22 December 2008

How I fail to look fully cute or ladylike in winter

By: Jessica B.
Tagged: Chicago, Fashion

I don’t consider myself to be a vain person, but I like to look nice when I leave the house (unless it’s Sunday, when showering is putting forth enough effort for the day.)

Looking cute in summer is easy, but winter provides a few more challenges, thanks to the cold and snow. In Wisconsin, I drive everywhere, so looking cute is easier because I don’t have to worry about public transport or much foot travel. When I moved to Chicago, someone told me, “in winter, you sacrifice how you look to stay warm.”
This was a foreign concept to me, so I ignored her, and boy did I pay for it. Now when I buy coats or boots, I always ask myself if they will survive a Chicago winter. If not, I don’t get them. My stepmom is routinely horrified by the “unfashionable” items I purchase because they’re “durable.” My usual response is, “they may not look that cute, but they will keep me warm.”
But in the essence of staying warm over fashionable or ladylike, I started thinking about the fashion/etiquette faux pas’ I commit regularly in winter and I decided to make a list:
  • Pant leg tucking – I don’t want to ruin my pant/jeans legs with the snow/salt, so I tuck them into my boots and, gasp, the pant’s aren’t skinny leg, so I have a mild Pied Piper look going
  • Public nose wipe – I get a runny nose easily and I don’t always have the time/ability to reach for a tissue (especially on the bus), so I just use my hand, sometimes more than once to wipe away snot. Yes, I know, it’s gross. It also looks like my hand is feeling up my face
  • Scarf flap – I actually saw in a fashion magazine in a “tips about wearing a scarf” article that having the tails peek out from the bottom of your coat is a big no, no. Too bad I don’t care and routinely look like I have a crotch flap 
  • Pick a color – I am a routine offender of not having a matching hat, scarf and gloves. If I’m lucky, the hat and scarf match, but not always. I hate being that matchy-matchy and sometimes, I grab for whatever accessories are closest to me, thus resulting in a color-blind-like palette of color when I go out
So that’s my list. I feel cleansed now that I’ve said it out loud. And anyone that judges is free to come visit Chicago, especially when we get pummeled by snow and see how you feel. Several ladies learned last week that Uggs are not appropriate snow attire (but I still love them!)
Does anyone else have similar winter fashion shames? 
Well the holidays are almost upon us, so I will be taking a few days off to be with family and try to hone my cooking skills (pictures forthcoming!)
Although I’ll be away from the blog, I will be tweeting my way through the next few days, which will be full of FAILs, inappropriate comments and forced family bonding. So if you don’t already, follow me on Twitter for the full adventure.
I hope everyone has a happy holiday and I will be back shortly. I will definitely want to hear what Santa brought everyone!


  1. dolcechic says:

    I hope you had a Merry Christmas!

  2. erin says:

    I think I posted about this last winter or the winter before. I always look like a bag lady in my winter gear, but I don’t really care. I’d rather my face be covered in scarves and my pants stick out of my boots than freeze and ruin my pants.

    I’d like to say everyone gives up on looking cute in the winter in Chicago, but I’d be wrong. Those fools who attempt looking cute? They FAIL majorly (generally by ruining their stuff or face-planting in the ground).

  3. EP says:

    I’ve never lived in a really cold climate, but even when it gets cold here, I’m never matching and don’t necessarily looks ladylike while out in the cold. (True story: My dad and his new wife bought me lots of warm, outdoorsy Christmas presents because they know I get cold.)

    To me, if your outside in the winter and doing what you need to be doing, you should be excused for any fashion magazine faux-pas.

  4. Athena Valentine says:

    I am visiting BF’s parents and family in Michigan and I packed alot of cute crap. But I learned, I will constantly be running around in a huge sweater plus coat in an effort to stay warm. I will also be walking like a penguin to avoid falling on ice. :)

  5. Rachel Burton says:

    Oh, I do all those! I pretty much resign myself to looking like a bag lady for four months out of the year. But at least I’m a warm bag lady…

  6. Dingo says:

    I start out the season with matching winter wear but by early December, I’m stuck wearing whatever I haven’t lost. Yes, I’ve gone out with one brown glove and one black one. What of it?

  7. mycynicalpov says:

    Hahahaha, I love that you admitted wiping your nose with your hand. I do the boot thing, too. And I wear a hat that looks like something a grandma from England would wear when I am going to work and it is snowing. A girl’s gotta stay warm!

    Merry Christmas.

  8. Rebekah says:

    Oh, but I love my winter clothes! Scarves, coats, hats! BOOTS!!!

    I never look ladylike in summer because somehow my legs are always bruised and/or bug-bitten. You’re not supposed to look ladylike when you play in the snow, but I think you are adorable :o)

  9. susan says:

    This is such a good post – I am totally with you – Boston winters are pretty treacherous too. The good thing is, I usually have to bundle up so much that you can’t even see my face, so there is the plus.

  10. bianca says:

    HAHA omg I’ve totally been thinking about fashion faux pas that I’m committing now that I’m in this ridiculous winter weather. You really got me with the “nose wipe”. That’s the worst but I totally do it! I swear you can’t help it when wind is attacking your face. I also don’t have winter boots (gasp!) since I wouldn’t get a lot of use out of them in CA, so I’ve been rocking my cute pink and purple kangaroos which would be fine except the majority of my sweaters don’t match so once I take off my coat I look ridiculous.

    I hope you have a fabulous holiday! I’m here until Jan 7th so maybe we can plan something when you get back!

  11. Miss Adventurous says:

    Winter fashion shame = snow boots.

    I don’t know how some women walk around the city in the snow in their hot stiletto-type boots, but that is way out of my league. Snow boots all the way.

  12. Joy @ Big Time Fancy says:

    Hahaha, things that are necessary for surviving a Chicago Winter:

    – a coat that strongly resembles a sleeping bag.
    – lined waterproof boots that go to the knee
    – hat
    – scarf
    – mittens/gloves/glittens
    – another scarf

    But by some miracle, all my wintery stuff is somehow matching this year. Hooray berry purple-pink and navy!

  13. Mega says:

    1- My favorite phrase from this blog post was “crotch flap”. Hhahahaha

    2- I always look sexy no matter what I’m wearing. In short? Me, FTW.

  14. Megkathleen says:

    There is nothing wrong with tucking your pants when there is lots of snow on the ground! I hate the snow and how cute shoes are impossible. That depresses me more than anything.

  15. Erin says:

    I get laughed at all the time because I bring my shoes to school rather than walk through the snow in them. I’d rather have dry feet all day, thank you very much.

  16. Megan Lagesse says:

    Gosh, I don’t know what you’re talking about. I always look fantastic during the winter. My marshmello green coat really lends a hand in that :)

    Merry Wisconsin Christmas, you should pull over at Mars Cheese Castle and snag some smoked string cheese.

  17. Hope says:

    Oh how I love me my uggs!!! Even though my feet are constantly wet…….

  18. Coconut says:

    I would rather stay warm and dry than look fashionable, even though I work in fashion. I wear black 90% of the time, and my Uggs are dark brown, so it never really works out. And I bring big-girl shoes to work, but my Uggs usually don’t make off of my feet. I look pretty hot.

  19. Angela says:

    We’re not Emily Post. Your fashion faux pas don’t matter! It’s winter–hell, stay as warm as you need to be! It’s not as if the bum on the street corner looks better than you do!

  20. Katelin says:

    i always have the scarf flap and i do not care, haha.

  21. A Super Girl says:

    I, too, do the pant leg tucking. In adition I hate hats, so instead I use this really long, rainbow colored scarf I have and wrap it around my head to cover my head/ears and then wrap it around my neck repeatedly so it stays put. Not fashionable at all!

  22. G+D says:

    LOL! And as far as that pied piper pant tucking thing goes–*raises hand*–I’m guilty as well.

  23. Little Miss Obsessive says:

    My coat I wear pretty daily is beige with some brown but I wear it all the time with Black Uggs… I don’t care! My Uggs are warmest and it’s my warmest coat! Heh =)

  24. Deutlich says:

    I find I sacrifice fashion for warmth because I just can’t stand being cold.



  25. Miss Merry says:

    Is this true? Do I need to invest in a puff coat and snow boots? people don’t bother looking cute in an effor t to stay warm? if so, that’s awesome, because here in the big D people would NEVER sacrifice looking cute for feeling warm. i will welcome the change.

    but really, do I need to buy some heavy duty winter gear?

  26. Vanessa says:

    I’m with you, stay warm and if it happens to match all the better. Priorities people!

  27. The Maiden Metallurgist says:

    One big difference between Chicago and Denver I’ve noticed since I’ve moved here is that everyone here is so put together and she-she. In Denver we’re much more sporty and utilitarian. I don’t worry one iota about being cute, I just want to be warm.

  28. laura marie says:

    I’m obsessive about cute winter wool coats and wraps. I have thus far refused to purchase anything considered ‘puffy’ or made of nylon to wear outdoors since I was little. But then I go and wear a $1 beanie hat from Dollar Tree and black rubber boots from walmart.

    I have awesome priorities.

  29. Nilsa says:

    AWESOME post because anyone who lives in such a cold-weather climate should be nodding their head with you! My big fashion faux pas? Wearing fur-lined boots with snow pants and a 3/4 length down coat with a big furry hood over a wool hat (complete with tassels) and bit down mittens. Look, a girl’s gotta walk the dog and spending 30 minutes freezing is not my version of fun.

    Since I don’t do Twitter, I guess this is goodbye for a few days. Have a great holiday break!

  30. Erin says:

    Pants tucked into boots? Got ’em. I refer to them as bloomers. My coworkers says she feels like a paratrooper.

    The non-matching winter wear? Got that, too. Pink and brown coat, purple or red scarf, pale blue hat….with kitty ears. It’s the warmest hat I own!

    I’m still working on the boot situation. I currently wear my black rain boots with heavy socks. It’s not cutting it. I’m hoping that Lands End or REI will have AWESOME post-holiday sales and I can buy a pair of non-fashionable warm, waterproof, clunky boots for less than a million dollars.

  31. Jess says:

    I am trying to remind myself that eventually if we live somewhere cold, I’m going to have to deal with this problem. For example, hats on curly hair? Not a good look, but still better than losing an ear to frostbite. And durable, waterproof snowboots with traction? Also not what I would go for if I were making a fashion choice. But necessary, maybe, someday.

  32. emmaelizabeth says:

    haha I live in MN and I think I committ all these “fashion crimes” as well. I no longer care what I look like when I go out in -12 degree weather with a -40 degree windchill… when it’s that cold, no one’s looking at you anyways. i’ll admit though, i found it funny when your stepmom is ‘horrified’ by your durable choices. my mom has ALWAYS told me i should just be warm rather than fashionable. at 24- i’m finally learning that lesson!

    keep warm!

  33. liz says:

    Over the years, I have gotten much better at looking cute when I am super bundled up.

    I think the key is to have wintery accesories that not necessarily match perfectly, but look alright together.

    I’m going snowboarding on Friday and that is where I will have trouble looking cute.

    I can’t wait for spring!

  34. S. says:

    Frostbite is not so fashionable. Stay warm!!

    Hope you have a great holiday!

  35. SBW says:

    i hear ya. so much easier to be a lady in the milder weather months. i recently noticed that i’m not wearing heals as much…probably has to do with the 25lb toddler that’s attached to my hip :) but i had this revelation over dinner w/my hubby. i don’t remember the last time i put panty hose on, and of course this brrr weather does not entice me to do so. bundle up and be cozy. i dig the red nose people get from the cold thought. it’s kinda sexy.

  36. Princess Pointful says:

    Hat hair! I loathe it so.

  37. Heidi Renée says:

    My sister is convinced that her Uggs will be just fine for walking around in the couple feet of snow currently gracing Michigan. Um, no. And I will laugh when her feet are completely soaked and mine are toasty warm in my big clunky boots. I may not be cute, but at least I’ll still have toes when I come back to Massachusetts.

  38. distractedspunk says:

    I have the opposite problem. I never manage to look coordinated or put together in the summer – more like I just grabbed whatever was available.

    But I invested in some great heavy peacoats, and I’ve always been big on the scarves and hats and gloves – though I’ve lost my brown hat and glove, so I’ll have to replace that. I also invest in mega socks, which means they go up to my knees to wear.

  39. Brandy says:

    My winter fashion no-no? Uggs. But I’ve ranted about them a lot lately and I secretly enjoy them, so are they really a ‘no-no’ to me?


    Also? I’m a girl (who living in Canada in the winter) has roughly 900 pairs of mittens,hats and scarves. But damned if I ever leave the house wearing anything that is even remotely matching. I’ve just accepted that I will never match wearing winter gear. I sleep easier.

  40. Maxie says:

    I’m practically never outside so I do a horrible job of wrapping up.

    I wore short sleeves today… yea like I said… I’m pretty bad at staying warm.

  41. Lacey Bean says:

    My mom used to always yell at me (not seriously) if my scarf didn’t match my gloves. She also yells if my toenails aren’t painted in the summer.


  42. Classy in Philadelphia says:

    Hahaha, omg this was seriously so funny.

    Especially the scarf thing! I used to do that, but now I find that i’m warmer if I just make it go around my neck as many times as possible.

    I def. don’t ever look cute in the winter….

  43. Maki says:

    Winter is so much fun to dress up, but it requires extra attention which was a pain when I lived in NJ.

    I used to have the same problem with my nose…

    Have a wonderful Christmas, honey!!!


  44. Mandy says:

    There is no way to look cute and be durable at the same time. My accessories never match.

    Have a wonderful holiday Jess!! Merry Christmas!!

  45. Rebecka says:

    just wait until you have kids! it gets better! :)

  46. Kyla Bea says:

    It’s completely impossible, I’m with you. Maybe if you live somewhere where jackets are a fashion thing and it’s not really cold, but my out door walks these day involve a face mask so I don’t get frostbite.

    I’m with you – I’m waiting for spring!

  47. andyhannon says:

    I never look ladylike?

    But now that its winter, I have a black and yellow jacket, jeans, brown boots, a purple and gray scarf and a black hat.

    I’m clash-man!