Chicago Confidential. A New Yorker’s Fashion Perspective. Part 1. Second City Style Fashion Blog

December 5, 2007 • Fashion

As a New Yorker, I’m used to city snow and I’ve come to expect it in December. But as a New Yorker on her first visit to Chicago since she was 10 years old, I didn’t realize how quickly Chicagoans grow accustomed to a white wintery wonderland.

Take in the current Chicago scene, where about 3 to 5 inches of snow have been dumped on this lovely Windy City.


Ironically, I’m not sure even this much snow would have phased the fashion scenesters in NYC who are most likely to take the garbage out in a pair of heels, and wear the most stylish pair of leather boots even when the weather outside is frightful. (Think SJP wearing white stilettos while filming a winter scene for Sex and the City.)


I wouldn’t be surprised to see your average NY glamour girl wearing the loveliest (most couture) cashmere argyle sweater or a luxe cloche hat to look chic and keep away the cold at the same time.

Chicagoans are a bit different. For better or worse, it seems to me they don’t really glam it up like us  New Yorkers. In other words, they’re more worried about staying warm (and staying comfortable) then they are about looking trendy. Unfortunately that means I’ve seen lots of uncomfortable looking wool hats, cable knit scarves, and (UGH!) Ugg boots!

In my opinion, New Yorkers overall have an edgier style. They are less conformist then I’ve noticed with Chicago folk–for obvious reasons. Chicago people are worried about the weather and you know what that means, if you’re a trendy New Yorker, you’ll be a hit in this fair Second City. And you’ll teach those Chicagoans a thing or two about how to dress it up–NYC style! And if you live in Chicago and you love it–show the rest of your neighbors how to dress right!

Too many Chicagoans look like this right now…


…when they really should look more like Chicago’s trendy tarte Heijy Choi, owner of Milwaukee Ave. boutique Hejfina.  (More on this haute spot later!)


And perhaps a cue from New Yorkers…

Next up:  Take advantage of the fab fashion Chicago DOES have to offer.  Take a stroll down Milwaukee Ave. in Wicker Park/Bucktown where you’ll come across four fab boutiques.  I’ll give you a little preview in Part 2–coming up!

Photos: Hollywood Rag,, Lucky
–Simona Kogan

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4 Responses to Chicago Confidential. A New Yorker’s Fashion Perspective. Part 1. Second City Style Fashion Blog

  1. Lauren - SCS says:

    Great job! No truer words were ever spoken. You picked up on the my biggest complaint about Chicago…nobody gives a damn when it’s cold. It’s easy to look glam in Chicago in the winter…all you have to do is put in a modicum of effort. However, admit it…it’s nice being the best dressed in the crowd, right? It’s like fishing in a bucket. Too easy if you’re from NYC.

  2. Joanne-SCS says:

    I agree! I’m not a native Chicagoan or Midwesterner for that matter so it was culture shock for me too. That being said, it’s so easy to look at the tourists and mistake them for residents… which could be more disturbing?

  3. rachelh says:

    OK, native Chicagoan here. I won’t even try to excuse the Ugg boots, and I’ve never been to NYC during a winter storm. That said it’s generally accepted that in Chicago, wait 5 minutes and the weather will change. That means 1 inch of snow an hour, then ice rain, then temperatures below 10F, then temperatures back up in the 40s all within a business day. When it changes so fast, and when things are freezing, melting and refreezing, it makes for a treacherous, able to stain anything (including black) winter mix/sludge. I think that, combined with the fact that Chicago is, admittedly, less edgy when it comes to fashion, is why you see a focus on comfort/warmth over style.
    I guess my hope would be for more recognition that comfort and style don’t have to be mutually exclusive. Still, you would never catch me walking around Chicago in stilettos in this sort of weather. I think I’m OK with that =)

  4. Lauren - SCS says:

    Sister…I hear ya! In no way are we saying one should wear their Loubies in 4 inches of snow (that’s just crazy and dumb), but there has to be a happy medium. We are saying, just try a little harder. Snow does not mean wearing your flannels in public.
    Listen, I have a dog and when I have to walk him in NYC or Chicago and it’s below 30 degrees, you will find me in my Uggs. They are warm, but they ARE NOT A FASHION STATEMENT. You will never catch me out on even Saturday strolling around town in my Uggs, however. They are simply too ugly.

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