This isn’t fashion, it’s a coping mechanism

Just some background…

I’m born and raised in California, then I went to college in North Carolina (Go Heels!), and for the past 4 1/2 years, I have lived in Cape Town. Do you see the common theme?

I am a cold weather sissy. I’ve never dealt with snow or extreme winters. Something tells me I’m in for a surprise here in Chicago. We haven’t had any snow YET, but its been downright cold, and everyone tells me this is mild.

My method for getting dressed is…layers, layers, layers, and something to cover my ears and hands. I also have had to get on board with practical (i.e flat) footwear.

Grey tank, lululemon racerback. white henley, Spendid. Flannel lumberjack shirt, J. Crew. Vest, Esprit. Pants, H&M (HERE). Boots, Sorel (via Zappos). 

I have really worked to clean out my closet in the past couple weeks, so now I am focusing on cold weather appropriate clothing to help me cope with this winter. 
When it first started to get chilly, I browsed Zappos and ordered these two:

I kept the “Conquest” (shown in outfit above) even though I feel like they are outside my style comfort zone. I struggle with casual wear, but I’m trying. I didn’t love the “Tofino” style, so I sent them back (free returns). Now I’m in the market for some other fairly flat black boots that I can wear in tundra that I’m about to experience.

Another thing I’ve been trying to embrace is skinny jeans. I used to think I would never be caught dead in skinny jeans because my legs are fairly thick athletic, but I have come around. Apparently, they are not as scary as I originally thought.

I tried on these coated modern skinny jeans from LOFT a couple months ago and have been patiently waiting for them to go on sale.  Black Friday came and went….Christmas came and went, and these pants are still $79. Everything else in the entire store has been on sale multiple times, but these edgy pants refuse to reduce in price and come home with me.

Luckily, I found these
They have the same coated black denim look and are a fraction of the price. They are pretty tight, but I have managed to squeeze myself into them and I’m digging them. 
LOFT loses. I win. The end. 

Thoughts on flannel? I was against it until I realized how cozy it is. Now I’m seeking out flannel…L.L Bean here I come. 

What’s your favorite jean style? I think boot cut is most flattering on me, but apparently this is yester-year.  

  • alyt27

    I live in Canada so I’m definitely used to the cold winters – I really recommend the Joan of Arctic boots by Sorel. They’re a bit heavy but there is seriously nothing warmer or more durable that these boots. Plus, the fur is kind of cute.

    The biggest tip I have about cold winters is to dress for them (i.e. cover all exposed skin!) and make the best of them.

  • Sprint2theTable

    I live in GA and I’m still all bundeled up. I hate cold weather!

    Flannel and skinny jeans with big boots are where it’s at!

  • Christina

    Ok, LOFT has been acting a fool lately. I usually buy so much stuff but haven’t in a while. With the exception of those sassy pants, I feel like they’ve been selling a lot of ooooldeerrr lady stuff. Or it just isn’t as cute. :(

  • Erin @ Loop Looks

    You know, I was all against Uggs for the longest time. But then I got some as a gift and decided that they are necessary evils for Chicago in the winter.

  • Pete B

    At this rate, we won’t get any snow this winter. My cross country skis will sit in the basement for another year!

  • casey

    it’s even cold in SANTA CRUZ. i’m so bundled right now..but i’m sure it’s no comparison to what chicago will bring—and the wind chill factor to boot?? #shuddering.. if you ever drop in american apparel, they have some “winterized” pieces..i love their “winter leggings” which are a thick version of the regular legging—they are so warm + thick! ..might help with the wind!

  • Catherine Crain

    It’s 70 degrees in SC today….crazy! I actually like those boots you’re wearing too, even though they aren’t

  • Katie @ Peace Love & Oats

    omg I LOOOOOVE Flannel! And I’m definitely pro skinny jeans! That outfit is adorable!

  • Camryn Stahlman-Dwyer

    Layering is totally fabulous right now! And flannel is in :)


  • Nicole

    Living in the Midwest, good boots are a must! I don’t wear flannel, but have a lot of fleece!
    My favorite jeans are GAP Long & Lean – they were discontinued in late 2012.

  • Shauna

    Love the Flannel!!!

    Quick question…Where did you find those jeans??? I tried clicking on the pic but the website didn’t come up :(

  • Sierra

    Shauna…try this link:

    If that doesn’t work, go in the denim section, these have zips at the ankles

  • Sierra

    I would love skinny jeans if I had your legs too

  • Sierra

    rub it in…I need a SC getaway

  • Sierra

    I haven’t been in there in years, but I may have to take a look. Thanks for the tip

  • Sierra

    I concur….loose tops and weird sweaters. Sassy is the perfect word for those pants 

  • Christina

    I love my sorrels! I have the tofino in red! They are warm and comfy. Since I have lived in the midwest my whole life I also recommend layering. I usually wear big bulky sweaters too.

  • Bryn

    I used to be a bootcut girl too, but have now embraced the skinny jean despite ‘athletic’ thighs ;) After living in a city where heels were no longer a daily wear because of comfort (and boot cut jeans don’t look so good with flat shoes!), I’m all about the riding boots and flats with skinny jeans. It’s all about finding the right tops to balance out the look :)

  • Bryn

    This might help: surprisingly I like the Target ones best!

  • Sallyeatsmke

    How do you struggle with casual wear?

  • Sierra

    I mean that I struggle to dress in a “jeans and tee” kinda way. I either like to be dressed up, or in yoga pants/athletic wear. Anything in between is tough for me to find a style that I like and feels comfortable/flattering.

  • Sierra

    I like a lot of these! Target ones look like Sorel

  • Sierra

    my balance = big top, off the shoulder styles. It’s really a distraction technique.

  • Kim

    SUCH a super cute outfit! Love it!

  • Paula

    I love, love those Tofino boots. Instead of sending those back, you should have sent them to meeee! :-) I so love Winter clothes and seeing all your cute outfits makes me miss Chicago. Why can’t Florida get it together? It’s Winter, it’s not supposed to be 80 degrees!
    Oh, and your blog is super hard to comment on now! Eek!