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Slipping out of the Mom Jeans and Looking for a Mom Skirt

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 Replies to “Slipping out of the Mom Jeans and Looking for a Mom Skirt”

    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 🙂

  1. 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.

  2. 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!

  3. 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 🙁

  4. 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!!

  5. 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.

  6. 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.

  7. 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.

  8. 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 😉

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

  10. 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.

  11. 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

  12. 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!

  13. 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).

  14. 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.

  15. 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.

  16. 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!


  17. 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.

  18. 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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