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Chicago Sun-Times
Chicago Sun-Times
Ismael Perez

Someone in Chicago wants to look stylish even in freezing temperatures

How much does the cold hinder our creativity to look nice when we go out for special occasions, or even go watch a movie on a Tuesday? (Angela Cheng/Sun-Times)

I was concentrating on staying warm while waiting for the train in the Loop when a young lady walked onto the platform and made me reevaluate my recent fashion choices.

The first thing I noticed, apart from her confidence, was her scene-stealing pair of boots. And then my eyes admired the attention to detail she put into her ensemble. The burst of creativity and the energy to care were a big contrast to what I was doing earlier that day — online shopping for warm joggers and sweatpants on sale during Thanksgiving week.

We sometimes want to run away from our youth, like when you walk into a Forever 21 and feel very uncomfortably above 31. Sometimes, we feel kicked out by the younger generation, like when Gen Z led a campaign on TikTok asking millennials to move on from skinny jeans.

Need advice?
Submit your question to ‘Someone in Chicago.’

But in that moment, as the Pink Line was arriving, I jumped at the opportunity to learn from someone in Chicago whom I knew nothing about. So I went up to the friendly-looking stranger and asked her for advice.

I dress up every so often. But I thought I’d ask a person who was at the height of self-confidence and self-love how to get there while feeling stuck in a comfort-over-fashion limbo.

Her name is Nailah Brown. She is a 19-year-old dance major at Columbia College, and this is what I learned from her:

Dress for occasions, big or small

As a dancer, Nailah says most of the time she can be seen in baggy clothing or athletic wear. And, yes, during the cold seasons, dressed in a lot of layers. But she likes dressing up occasionally, especially on weekends that present her with opportunities to bring out favorites from her closet.

What motivated her to dress up that day? A recent sale and a picture-perfect opportunity. More specifically, she bought flashy boots a day before and hopped on a train with a friend the next day to take pictures with the Christmas tree at Millennium Park.

Nailah Brown, 19, dressed up to take photos with the Christmas tree at Millennium Park. (Provided)

Making a plan is great. The challenge sometimes for me is getting over social anxiety before heading out the door because I know people will stare and might think I’m being a little bit “extra.”

Nailah recommends not taking offense to the stares.

“If I feel confident in that outfit, then I really don’t care,” Nailah says. “I don’t mind other people staring at me because at least they’re staring at a good outfit.”

Stay warm, healthy, wear what makes you feel good

With the weather getting disgustingly chilly, there’s a high chance we will end up walking down the street looking like Randy with the infamous snowsuit in “A Christmas Story.” And that’s fine, Nailah says — keep your health and well-being as your main priority.

A nice reminder for all of us, especially if we expect to wait in line outside a crowded bar or restaurant.

I think dressing in comforting layers or a bulky coat might make an outfit reveal even more exciting when you get to your indoor destination. Keep people on their toes. I also like to invest in bright-colored coats or dramatic, vintage store faux fur coats, to stand out from the average black or gray jacket.

Overall, I think the trick here is to remind yourself of the bad bitch that you are every once in a while.

“Just wear what makes you feel comfortable and confident, even if it’s sweats and hoodie,” Nailah says. “If you feel confident and wear it with style, then it shouldn’t matter what other people think.”

After our conversation, I went ahead and bought the sweatpants. No need to ask me twice. Check back next week, when I write about my online shopping problem.

Write to Someone in Chicago at or fill out this form.

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