I am not a skirt/dress person.  My view of the fashion kingdom has always been to keep a supply of easy to put on, no muss, no fuss articles of clothing that I could grab, slide on, and run out in.

Enter the husband.  Thanks to my summer tummy tuck, he seems to think I’m looking pretty good, and women who look pretty good have a whole different level of fashion expectations.  He’s like to see me in some casual skirts or dresses to wear this winter while he thinks I have nothing better to do than sit and have him admire the new figure.  Thats his view on the world.  Now for the reality.

I need skirts and dresses that are casual, comfortable, not frumpy, and give me a more polished look.  I don’t want anything sleeveless, because I freeze.  I’m not a huge fan of stockings, because, again, I freeze, so ideally, I’d like to do tights.  And just what kind of shoes am I supposed to wear?  I don’t like boots with short skirts, and you can’t really do heels well with tights.  What time is my appointment to be on What Not To Wear?

In doing extensive skirt/dress research, I did find a few things.

Don’t wear baggy – No kidding?  Did I lose 150 pounds and go through all this surgery to wear baggy?  I think not.

Pleats Please? – Ummm, no, you big fat arse.  I may have lost all that weight, but I still carry about 30 pounds too much, and pleats and gathers on a skirt just add poundage.  Unless you’ve been on the Lara Flynn Boyle diet lately, skip them entirely.  So now I know what I looked like all summer long – enormous, wearing pencil skirts day after day.

Remember the big fat arse comment? – Yeah, I’m talking to me.  No light colors on the bottom – especially if you are wearing dark on top.  Dark on the bottom in slimming; light on the bottom gives you bubble butt.  Nobody looks good in bubble butt.

The length of your skirt should not be determined by how desperately you want to look like Tina Turner.  Face it, sister, you don’t look like Tina Turner.  The woman is smokin’ in her almost 70 year old skin, and she can rock the mini skirt.  The worse your legs look, the longer your skirt should be.  That means I should only wear skirts with a cathedral train.  At least that’s how I interpret this rule.

So which skirts will look okay on me?

A-Line seems to be the skirt for everyone – even my big old butt.  They are fitted at the top, but then they get a bit wider as they go down, to accommodate those areas of my body that have not had the benefit of the work of the fabulous Dr. Veitia.

Wrap skirts are another style that seems like it would flatter every figure.  Are there winter wrap skirts?  And what shoes do you wear with them?

Straight skirts, now that I don’t have that hanging tummy, seem like they might work as well, but I’ve seen longer straight skirts.  I don’t think it’s a look I can carry, and I always think bag lady when I see them.  Seriously.

I still have kind of wide hips, but I’m not sure I know the difference between a pencil skirt and a straight skirt.  Anyone want to enlighten me?

I like the look of a flared skirt, but for some reason, I just always think they’re either for MUCH younger people or dancers.

So, who wants in on the skirt discussion?  Help a sister out, will you?

113 thoughts on “Slipping out of the Mom Jeans and Looking for a Mom Skirt”

  1. Hey,
    I love skirts in the winter. I have a pair of wedge boots that are very comfy. So don’t rule them out. I have found that Kohl’s has a great selection of skirts that are flattering. my favorite out of your pics is the last one. but I would want it 1-2 inches shorter and in solid brown, grey and black. Then they are easier to wear. If you get a shorter than skirt you can try leggings under it with boots. Use the thinner leggings though. I love leggings boots and long cut shirts…..There my 2 cents….hope it helps some!! Thanks

  2. Thanks, Chas! I was just looking online at Kohl’s LOL – I might end up there this week looking at skirts in person!

    Can an old broad carry off that leggings and skirt thing? I love the look, but it’s very “young” – I’ve got a lot of years on you!

  3. Ill make you a bet Anna – get 100 comments in this thread, and Ill give you cash for shopping for clothes and a $20 Starbucks gift card to a random winner out of those 100 comments.

    100 real comments, not 1 worders, or enter me. But something that helps you in picking out your clothes. People can reply to other people’s and your comments, but not to themselves.

    And you have to have it done within 7 days.

    Deal Lady?

  4. I’m a big fan of wrap and A-line skirts…but I haven’t worn a skirt in years (pre-kids, I wore them a lot. Post-kids…no way no how. Unless I HAVE to.)

    And pleats? No way. I spent 4 years at a Catholic High School rocking out the pleated skirt. That was 4 years too much if you ask me.

    I really like the picture above of the black/white skirt w/ black tights and really cute shoes! A classic look. Also like the straight black skirt (have no idea if it’s just a straight skirt or a pencil skirt).

    Best of luck! 🙂

  5. I love the wrap and flare skirts…if I had to pick those would be the ones I would wear.

    1. I like the wrap skirts, too – I just haven’t seen any in heavier fall/winter weight yet. I’ll have to keep looking! Maybe if I check OUTSIDE of the Disney Store…

  6. Anna,

    Not to add to all your questions of what to get, I am a skirt person that I like to look modest but attractive ( I am a mom of 2 & in my mid 40’s) so looKing “HOT” is out of the question and no longer my phase of life.

    So to really find that piece that is “you” will take a long shopping trip to several locations of trying on every type of skirt on. Also take your best critic mine is my oldest daughter, she knows my true personality and what I think looks good on the hanger might not look good on me. When I say try everything on what you think might not look good might surprise you.

    Now with shoes I am not a boot person either, dont like the feel around my fat calves. I had found nice block heels have done well for me.

    Good luck and I hope when you choices are selected you post runway pics 🙂

  7. I think a nice mid-calf length skirt with some boots and a cashmere sweater always looks nice. Black skirt, red sweater, some bling, black boots and then you can rock the red tights. 😉 Good luck.

  8. A-Line Anna for the win! Flattering for all of us girls.

    I was just searching today for the perfect a-line corduroy skirt to wear this fall. I ordered one from ll bean that said it was a-line, but they lied! It was straight up and down and really ugly on my plus sized rear end! So back it went! I was on the phone with my Mom when I tried it on and actually screeched which tickled her to no end.

    That Boden Catalog has some super cute a-line skirts…I’ve gotten a few off of ebay before that I really like. Nicely made.

    A true pencil skirt, or wiggle skirt, should end at the knees and have a very small slit in the back so that your stride is actually shortened and you get that “wiggle” walk… Think Marilyn Monroe! My Granny was known for causing a scandal around Montgomery, Alabama wearing her’s without a girdle underneath…the hussy! Heh. She was makin’ her granddaughter proud even then!

    Ok, I was NO help. But I got to yabber. I’m good at that! Hope you get a hundred comments and a shopping spree!! This should be fun!

    1. Lands End has some corduroy skirts!

      I have an LL Bean store near me, and I buy the kids winter stuff there every year. I find though, for me, I have to buy up a size or two in everything. As a fat chick, that’s the last thing you want to have to do 🙁 And their jeans? I don’t know what’s wrong with my arse, but I just can’t make them fit right in LL Bean jeans 🙁

  9. I love the wrap skirt. The pencils have never looked good on me because of my bottom. The flare skirts give more of a hippy look, and while comfy, that isn’t what you want. The footed tights look great with boots and decent with cute flats. I don’t love them with heels, but I don’t love heels. I do ask that you don’t try the gladiator shoes. I really don’t want that look to stay, and if you promote them they will take off again. 🙂

    1. I’m afraid of that hippy look in the flares, too, but they seem quite popular at the moment!

      No worries on the gladiator shoes. Nothing that has ever graced the body of Russell Crowe will find a home in my closet!

  10. Ok…I really, REALLY like the ‘flirtyness’ of the wrap skirt–and I think it’d look great on you!! You should come down to TX and we could shop ‘commando style’–trying everything on and getting a good idea for what is flattering for you. I’m a firm believer of it!
    Now…if only I could fit into MY clothes! *sigh*

    1. I am coming to Texas! We’ll clean out your closet then tackle shopping – all the unpleasantness out of the way, then we’ll go eat BBQ 🙂

  11. ok, so i am fashion challenged beyond measure, but i think the wrap skirt would be fine in winter, just heavier fabric, not the light summer stuff. as far as shoes, maybe a pair of those cute loafer type things they have now? you have got to post after pics!!

    1. I always loved penny loafers – I wonder if you can even find a pair of those now! I’ll totally look like I stepped out of the 50s 🙂

  12. Anna,

    I think you would look great in the A-Line and the wrap around skirts. Honestly though, you really need to go and just try on different kinds with an open mind.

    I totally agree with the no boots on short skirts. I don’t think its a good look on anyone. But then, I really don’t like the look of boots with anything except snow suits.

    Good luck in your clothing search!


    1. There’s a theme here among these comments, and it doesn’t seem to be the one I’m most comfortable with – the one that says “Order online and cry in private when you look ridiculous!” All of y’all are sending me out to the store to make a scene in public!

  13. I think if you can pull it off, a line knee length skirts are trendy. They make my size 16 body look a little heavier, and are very summery. I like a long skirt for fall and winter, with a cute pair of boots… if you have them.

    The difference between a pencil and a straight skirt, is the pencil is slightly tapered, accentuating or creating hips. So if you have hips, straight is better. But a guy will always like the hips, and a pencil skirt can be sexy.

  14. Anna,
    I think the A line, wrap or possibly the flare would look ok. A line is universally attractive. Flare looks a little sassy! Not sure how they look now that we are a little older. Wraps are a version often of the a line usually. Enjoy shopping!!!

  15. Great site………..LOVE the skirt thing – gettin’ out of the mama jeans!!!!!!!!!!!!! GO GIRL!

  16. Anna,
    I prefer the flare skirt or the wrap. If you go with the A-line, a nice suit style would serve many purposes,work,meetings.church, funerals. You could also change it out to make several outfits.
    Good Luck and congratulations on your accomplishments.

  17. The best thing to do is go shopping and try stuff on. You’ll never know until you see it on YOU. I personally like skirts but only wear them about once a month.

  18. Hi Anna,

    I have a fear of skirts, and, as a result wear pants, anykind of pants, as long as they are pants.

    If I HAD to select a skirt, only because there were no more pants in the world, then, for my body type I would have to resort to the A-line type of thing. As much as I love the pencil type skirts, I would look like a Kelbassa sausage in one of those, and then walking in high heels…I would be a sight for sore eyes….

    Good luck with your quest, I have a feeling you will get that clothing spree regardless of how many posts you receive today. Jim seems like that kind of a hubby….

    Have fun,
    Jackie Psarianos

  19. I love wearing long skirts – any color, any print. I wear them with my ‘granny’ boots (think Little House on the Prairie, lace up, etc.) In the summer I wear them with ballet-flats or maryjanes. For the top, I keep it coordinating but fairly simple. For me, it’s still very comfortable (no pantyhose!) but dressed up. Perfect for the office, a wedding and a funeral and I’ve worn this look to all three!

    1. I used to have those boots! I wore those puppies out in the pre-children days – I think I wore them with nearly everything I owned.

      I so need to shop.

  20. Not a skirt person anymore as I spend too much time crawling around looking for books on the bottom shelves at the library.

    I agree that pleats are out, unless you are wearing a ladies’ kilt in your own tartan. But I love the flared skirt! No, it’s not just for younger babes; us older babes can wear it too. It looks great with a jacket or sweater, in dressier fabrics for work or parties, or in a more casual knit (Lands End may carry them–haven’t looked recently)for weekends or less formal occasions. They are a bit flirty, yes, but give great coverage when you are sitting (and need that extra fabric to keep your legs warm).

    Tights go well with low-heeled shoes that tie or have a kiltie style to them. See an example in your straight skirt photo. And with a straight skirt and tights, you can go all Audrey Hepburn and wear flats, which are very in right now.

  21. How do you feel about shopping and trying things on? In your position I would head for the mall for the afternoon, maybe with a few girlfriends in tow. Grab “one of everything,” try them on and take a good look in the mirror.

  22. I hate shopping, and lack very many local real life girlfriends. Okay – all you guys need to come to Jersey and shop with me!

  23. Anna-I definitely think the A-line, wrap, or flirty skirts are best. For shoes, if you don’t want high boots, or high heels, you could go with an ankle boot with a wedge heel. But ultimately, take the time to go out and shop in person, and try everything on. It’s all about what’s comfortable for you!

    Happy Shopping 🙂

  24. I am a fan of straight skirts and then “A” line skirts. Not a big fan of flared skirts, they remind me of my grandmother. Good luck with the 75 comments! Hope you get a shopping spree out of all this and some ideas as well. Enjoy shopping my friend!

  25. Anna, I am a professional bubble butt and I have always liked the A-Line. Not only is it flattering to almost all shapes it is also easy to move around in.

  26. I’m not a big skirt person either but you are brave thinking about it for the winter. I’d freeze ! When I worked in Corp america before kiddos I did tights too and usually ended up with ballet flats as I just don’t do heels but that’s probably not fashionable these days. I love the look of the simple jersey dresses that have that wrap look to them. They come just a bit past the knees and fall really nicely without adding something that’s not there

    1. Tanya – how forgiving are the jersey knit dresses? I have seen a few of them, and like the look, but I have bigger features on top than I have on the bottom, including some serious back fat Do you have to wear something over the dress to hide the flaws?

  27. How tall are you? I think the long pencil skirts look nice on women who are taller than average. Otherwise I would probably go with flair – they are cute. I have never thought A line looked good on me. I hope you find one you just love and have to have!

    1. Bec – I’m about 5’7.5″ tall – and I’m not sure about A-line. I am listening to how they flatter every body type, but I don’t think they’ve seen a body quite like this one LOL!

  28. I personally love a lines, I think they look good on everyone. I’m a a line girl living in Wisconsin with a hooker shoe fetish!! Anytime I get to wear a skirt with some great shoes or boots is a fantastic day No lie!
    Since we’re in the frozen tundra it’s not very often, but as often as I can make it!
    Good luck!

  29. It really depends on how tall you when determining what length of skirt to wear, just my personal opinion. It also depends on your age. I also think if you work outside the home that also determine what type of skirt/length you should wear. Have fun shopping. I am 3 weeks postop RNY and I am really hoping to get where you are!

    1. Congratulations, Cathy! I hope your recovery is going well and you were well on your way to Loserville!

      I don’t work outside the house, but I volunteer at school three days a week, and I go to school three days a week. On top of that, I’m trying not to look like I just rolled out of bed – it helps detract from my short comings if I dress better LOL!

  30. I’m not a skirt person either, but I think A-line is usually flattering on everyone….but with your beautiful new figure I’m sure you can carry off any of the styles you want to 🙂

    1. Michelle, that’s so sweet! But this is a body like no other, and not quite at the “beautiful” stage yet!

  31. Skirts pose a professional hazard to me as a preschool teacher but even on non-work days I can never seem to find one that makes me look skinny. Possibly this is due to the fact that I am no where near skinny. Perhaps when they invent that miracle skinny skirt I will be back in fashion!

    1. Well there it is, my problem in a nut shell – I also have not found the miracle skinny skirt!! As soon as they invent comfortable high heels, they’ll get right to work on this. And male birth control pills.

  32. Wrap tops with an A-line skirt seems to work for most ladies. Enjoy all the new clothes you will be getting.

    1. I have quite a thing for wrap tops – I love them! I have three at the moment, but have no trouble talking myself into more 🙂

  33. Anna, you and Jim crack me up 😀

    I was in Macy’s yesterday, and I saw a lot of sort of retro-ish winter skirts in plaids, but really subtle plaids, not like school uniform, and the skirt shapes were more modern, like flared and a-line. I think this is EXACTLY the kind of thing that would be awesome with tights for winter, and wouldn’t need a boot. I can’t find any of these skirts at the Macy’s website, but here’s another example:

    And I think you could do this type of thing instead of a boot:

    1. OMG – love the shoes!! The skirts remind me of old Church ladies, but hey, if that’s the style, maybe I need to get on the bandwagon!

    2. YES! Mel, those are the kind of shoes I was thinking of too. I love that clunky/chunky shoe with a skirt. I guess I don’t know the right word for it. I’m not a fashionista. Tim Gunn would barf if he looked at my wardrobe. But these are the right shoes to wear with a skirt and tights, says I.

      And a shorter skirt, a little above knee-length, to show off some leg, because it would look awesome:

      Again, sorry if my taste is terrible. I just want you to at least TRY the short skirts!

  34. I like the wrap skirts and the a-lines, myself. Although I’m not really much of a skirt wearer, being that I have to shelve books in my library. I’m sure you need to spend a day or two shopping–maybe take one or all of the girls???–and trying things on to see what you think looks best on your new figure.

    Congrats on the weight loss!

    1. Anna,
      Since I my self have not been in a skirt since probably back in my Catholic High School days. Not that we wore skirts. Nooooo, we wore those not flattering on anyone not even Britany Spears,
      JUMPERS. You know the ones. With the lovely little white blouses under them.
      Anyway, Kohls would be where I would look, if I ever wore one again. Ha.
      And they have great online shopping.
      Have you tried New York and company? I have spent many a day in their dressing room as the personal coat and purse holder while my daughter(s) shopped.
      They have a great array of sizes, and styles for all shapes.
      Good luck!

  35. I can totally understand the bubble butt comments I myself dont oftn wear skirts. I dont feel like I can mix and match them as well. Skirts seeem more formal an less comfortable. I am black pants nd shirt kind of girl, this is by neccessity usually as I need something fast to put on too :-).

    Ive found that dresses the maxi style (not super long) are very flattering and somewhat stylish, they usually have an interesting neckline and you can sort of throw them on 🙂 I bought a few non printed ones a few years back and some printed ones too. I feel like I can use them for everything in a pinch swimsuite cover up no problem, throw on to go to the store no problem a much needed breeze on a cool day no problem.

    Good Luck I hope you get enough comments to go shopping hmmmm maybe my husband should start a contest (I wish LOL!)

  36. A-line are good – make sure the hem is good; too short or long will kill the look of a skirt in a second. Good luck!

  37. I love the look of wrap skirts! But even if I wasn’t the Queen of cotton knit pants for myself I think my 2 year old would untie it!

  38. I am a fan of the wrap skirts – very forgiving and oh so cute. A-lines are nice too, and can be worn with a variety of shoe heights. Good luck with your choice!

  39. Anna … You have to try them on. I know you have heard this above, but that is so important.

    The more fitted, the better. SHOW you have a waist babe – you earned it. Flatter the entire figure – that is what matters in the end. To pair a nice fitted skirt with a baggy top will just do you a disservice.

    And – take multiple friends who like to shop. Show the legs, add some heels. But I’m not a tights girl, so I can’t help in that respect.
    I think the mid-length skirts look best – the extra long ones rarely look flattering.

    1. Okay – as soon as Beth is back from her vacation, you guys need to grab Melinda and head to Jersey – we’ve got shopping to do 🙂

    1. Funny, that’s the one Jim preferred as well!

      And how dignified is that – comparing me to an E-ticket ride? The nerve…

  40. i think the second skirt with black or white leggings and boots would look very cute. a fitted shirt would work well or a cute fitted sweater, not a bulky one. think this is an skirt you could have fun with and dress up or down.

  41. Okay my 2cents… I am long legged short torso so I do NOT do wide waistbands and I do NOT do pockets because they make me feel like I do look wider. Straight skirts work for me but I go just below the knee to make sure they don’t make me look like I am trying to be 20. I wear tights with my skirts at work – I find penny loafer style shoes work with them. I wear my sweaters with them and don’t do blouses – I have a larger top so blouses and me do NOT get along.

    Good luck with the shopping. Post pics of what you get!

    1. I’ve noticed quite a few while looking online with the wide waistband – it looks like a cummerbund that you would wear with a tuxedo.

      I am not terribly fond of blouses, either, and think I’d lay in a few sweaters.


  42. I have noticed more and more moms on the playground wearing skirts vs. shorts or pants. Personally, I am a blue jeans kinda mom. Can’t go wrong with denim and a long sleeve tee in the fall. If you do go for a skirt, make sure you are comfortable in it 🙂

  43. I vote for the longer A-line for fall. I have seen many folks pull that off with a pair of ankle or knee boots peeking from underneath. No legs need to show at all. No tights or stockings are necessary; you can wear nice warm socks. But a pair of spanx underneath the skirt could certainly take the place of tights and add a little extra schlllluuuuup (sucking-in noise). Hope you reach your goal!

  44. I love tights. If you go with some cool chunky shoes you can do the grown-up schoolgirl thing. Keep the skirt short. In tights your legs will look fab with a short skirt. Beware the below-the-knee skirt because they are eeevil unless you are a gazelle.

    If you get your skirt fitted but with room to move, above the knee, you will look like you are comfortable with yourself and THAT is sexy.

    Okay, you know I don’t know jack about fashion. So maybe ignore me. But I still think that dark opaque tights hide most leg ‘flaws’ and so you should go with shorter fitted skirts.

    1. I’m liking the tights – maybe they won’t look as “young” as I think they will. On to more research!

  45. I think that tights are in again, plus the cute little slipper shoes are stylish. So you should be all set there. I think you already have some great ideas! Enjoy your new look!

    1. Thanks, Melissa! How could I go wrong – new skirts, new shoes, new tights – it’s going to be a happy fall!

    1. Not sure I can rock the pink – maybe I’ll just get a skirt with a pink lining! I look like a Pepto Bismal accident in my Moms Panel attire!

  46. I love the flared skirt look – very big this season and so feminine and pretty. You could totally care it off!

    1. I’ll have to see a few in person – most that I’ve seen online remind me of the old school marm – only hipper 🙂

  47. I love the wrap and flared skirts too and totally think you can pull those off!! I love when your hubby does reward contests like these!! I know you’ll make it!! Off to spread the word!

    1. And she’s so emaciated that with her feet together, her thighs don’t come anywhere near touching. Eww.

  48. I don’t really know what clothes you should pick, but you’ll know what makes you feel the best when you try it on. Just wanted to comment to help you get your new wardrobe.

    Have fun!

  49. I think you should go with the A line skirts. With winter, you can wear tights, and flats and still have a sexy look, yet comfortable. However, depending on your style of tops your skirt style may also vary… So shop at Macy’s… they usually have a personal stylist that could help you. Congrats on your sucess…keep it up and keep us posted…
    YOU go girl!!!

    1. Oh my gosh – Macy’s has nine pages of skirts online! I had no idea! I usually only get makeup at Macy’s because our Macys seems filled with things from Baby Phat and Jennifer Lopez. I so don’t fit those collections 🙁

  50. I love it! Keep the length just at or just above the knee. Any longer cuts off your (ok my) calves and makes you (ok me) look like a wrestler. Is that a “real” enough comment Jimbo? Go Anna go!!

  51. Whoa, that model is creepy looking! I understand that they want us to focus on the clothes, but between her facial expression and her arms hanging lankily by her sides, the site looks pretty unappealing.

    Your skirt quest is an interesting one. I understand your hatred of shopping but maybe just go to one store and try a few things on, just so you start to know what you like and what you don’t.

    I used to wear skirts but haven’t in a while, mainly due to not being able to find attractive looks in them at my weight. I do wear dresses some; in the summer especially I like a cool-feeling dress. You might take a look at dresses as well; it is possible you might see something that will be comfy and attractive for you.

    I agree with the above commenters; go for the tights. They will look fine and will keep you warmer in cold weather!

    1. Oh yes – I am aiming to be the next Tina Turner. All I need now is:

      The antidote to the Michael Jackson miracle race changing formula.

      Parents with WAY better genes.

      A hair stylist who will not have me committed when I show her the picture of the hair style I’ll need.

      So yeah, it may take me a while.

      And call Mommy – she wasn’t feeling well yesterday.

  52. Anna,
    I love skirts but do not wear them. Love the wrap skirt…but I think what you are just going to have to go try them on. Do they still have shoppers at Macy’s or Nordstorms maybe you could call and set up an appointment but 1 outfit but they give you options for others and suggestions. What Or call Clinton and whatever her name is from what not to wear =)

    1. That’s what I need – the What Not To Wear crew – except I’m afraid that once they looked into my closet, and pulled out everything I shouldn’t be wearing, I’d be left bare arsed and freezing all winter long.

  53. I don’t know which will look best, but I’m all for a $500 shopping spree! have fun!

  54. Anna, I hope you get 100! Does he not know how truly popular you are?
    Anyway, I think a longer wrap skirt would be perfect. Not too short, not too much flare. You could wear with tights and flats. I haven’t worn a skirt in YEARS!!!! Not sure I would want to. But I love the wrap and the flare, if I did.

  55. What is up with that model?? That is the posture and expression my mother assumes when she’s trying something on, and asking my opinion, and she wants me to tell her it looks awful so she can reject it and buy the other thing she already knows she likes 😉

    I think Macys is really not a bad place to start, just to get an idea of what might work, because they have a lot of different styles and sizes. I’m not sure what size you wear now, but they have such a wide range, and from my experience, they have tons more stuff in the store than what you see online, too. Plus, see, then you are already at the mall, and if you go through the hassle of trying on a zillion skirts, you can reward yourself with a new lipstick at Sephora 😉

  56. Why be frumpy? Skirts are so classy and sexy! I vote for A-line or flared. Hope you get to 100!

  57. I wore long skirts and flip flops all summer! Now that fall is here, I am going to give the leggings underneath a try. Boots too, since I get odd looks wearing flip flops these days. I love the wrap skirt, with a long sleeve tee, jean jacket and scarf I think you’de fit in anywhere!

    1. I’ve worn the long, flowy, broomstick style all summer long too. They were easy to get on and off around my wound and the wound vac. I was hoping to move through my hippy phase and into something chic-er.

  58. Wraps are great you should go to Salks or Dillars they have ladies to help you with everything and Jim can pay for it all

  59. Anna, go for the flare. It’s a “nice” look, yet casual enough to just slip on some flats or slides / mules & dash out the door. I personally think RESTRICTED when I think of pencil skirts – but then again, I still have a kid of the age where I need to be able to get onto the floor & back up LOL!

  60. Pencil skirts are simply not comfortable, if you are prone to walking or sitting that is. Go with an a-line or wrap for comfort — these are also more feminine (IMHO).

  61. Ummm…your daughter just got skirts for autumn and winter. And used to wear skirts and tights every day for school. Remember?

    Think wool and corduroy. Old Navy had super cute, but my Old Navy had mostly shorter lengths.
    Pick up black and brown tights, since they’ll go with any skirt colour you’ll buy and any shirt you’ll wear.

    If you get longer A-line lengths you can wear your Uggs, otherwise you have crocs which will look cute. And those crocs ballet flats will work, too, and the tights should prevent any blisters.
    If you’re not wearing boots or those fuzzy crocs and you opt for flats, just pick up some thin ankle socks. I used to wear socks and UnderArmour under my tights for school on the really cold days. You couldn’t even tell.

    And you can easily find regular waist and high-waist and longer length skirts because they’re very in right now, so you don’t have to worry about super low waisted or high hemmed skirts.

    I would hit Old Navy, Banana Republic, that Coldwater Creek store you like and Target. Or try the more expensive business-casual-oriented shops at Cherry Hill Mall – the money won’t stretch as far, but you might find some very nice quality skirts that are cute, conservative and comfy.

    I think a simple A-line or something with a little flare at the bottom would look nice, and you don’t have to worry about the longer lengths making you look frumpy because you’re tall. (jerk.)

    For something a little dressier, I would tuck in an oxford button-down. I think you still have a white one that would be cute. And you could add a belt.
    Otherwise, you have lots of nice sweaters that will look cute.

    Don’t wear a skirt with that grey wrap you have, then it’ll be too much volume – only wear that with pants.

  62. Anna, I think you’d look awesome in any of those! Being on the short side (5’2″), I tend to gravitate toward the straight skirts, full circular skirts that drape (but only if they’re hemmed by someone else – not me!), or the button-down-the front skirts. Pretty much anything that makes a ‘long line’. I used to do skirts whenever I had an occasion, now it’s only once in a blue moon. Maybe I’ll take some of Brighid’s shoe/skirt combo advice. I just can’t find anything I seem to like that’s not high heels.

  63. Anna… while I can not totally relate to the whole weight issue… I can relate to not liking how I look in certain clothing. After my hystarectomy I have gained alot of weight. For me, even though everyone else thought I was still thin, was a nightmare. I was no longer a size 5/6. I suddenly found myself wearing 11/12 pants/skirts/ect. So I had to get creative. I took pictures and lots of them. I remember going shopping with Hector, my ex… not my fiance, and having him take photos of everything I tried on. He hated it… but the outcome was awesome for me!

    I was able to see how I looked in an outfit before I bought it. At that time in my life this was crucial… first, I was not in a financial position to buy a lot of clothing… and secondly, I was going thru serious depression. The reality of my surgery was setting in. Not being able to have my own biological children was hitting me harder than I could have ever imagined. I started to regain confidence in myself. After all, wasn’t the one thing that made us important in the stream of life the ability to carry a child and give birth? I felt less than a woman… but was able to reclaim myself through small things like my clothing.

    I hope this helps you in some way. I love you always!


  64. Anna,
    Here is wishing you much success on your clothing search!! Your findings are a help to me too! I have also recently lost a few pounds (94) and will soon be doing a bit of clothing shopping myself!! My mother says I look “tacky” in my old clothes and has offered to take me on a shopping spree!! Woo Hoo!
    As for the skirts, I prefer the wrap, because they can be tightened or lossened to a degree. And as you said, you have 30 more to go, so it might help budget if nothing else to be able to wear them a bit longer.
    Shoes for skirts? Even tho I am a shorty, I still prefer those flats, especially in winter!! Ever seen a fat butt trying to pick themselves up after sliding down on the ice? LOL. I’ve always had a fear of falling, so I’m sure that is the truth to my reasoning. And you can wear tights or stockings with a skirt and both would be cute!
    Good luck with your search, let us know what you decide!!

    1. I agree about the shoes… but also remember the past always comes back. There was a time when i wouldn’t be caught dead in clothing from the 70’s, specially cause I’m an 80’s rocker….lol. Now the story is different. Boots with A-line Skirts is totally in. Whether you go knee high or calf high, you can not go wrong. BUT no matter what in the end, STAY TRUE TO WHO YOU ARE IN EVERYTHING YOU DO….. This applies to fashion as well.

  65. I’m a little late stumbling upon this blog and now am dying to know what you decided on! I’m all about the shoes … that’s the only reason I don’t wear skirts or dresses except in summer … I can never find shoes that don’t hurt my feet due to the massive bunion I inherited from my father 🙁 Post a pic of you in one new “look” so we can all see!!

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