This weekend I’ll be in Wisconsin, where I’ll play with my niece, eat plenty of cheese and fried fish with my fam, drink a couple beers, and run a 10k (not in that order). I’m excited. I mean, obviously. Babies and beer, what’s not to love?

But there’s a voice in the back of my head every time I visit that reminds me, “You look different than everyone else.” Usually I notice my city style on one of my ritual Target pilgrimages. It’s like those old Gap ads – Everybody in vests! – except it’s everybody in Packers sweatshirts, Patagonia windbreakers, and bootcut jeans! Meanwhile, I’m in all black with my hair doing who-knows-what and red lipstick, and little kids are giving me the side eye in the snack aisle.

City style

The longer I’m away from the Midwest, the more I feel separate from the Wisconsin aesthetic. I can’t talk much about sports much beyond my schoolgirl crush on Aaron Rodgers, and my outdoor hiking is limited to my morning trek to the subway. As for the bootcut jeans, well, we’ve discussed those before.

Of course, those who buck the trends are always easier to spot. There was a kid in my grade school who would wear skateboard brand t-shirts and sneakers when everyone else sported those Gap hoodies and Adidas sambas. A college classmate in Pennsylvania insisted on wearing almost exclusively surf brands, white tube socks halfway up his calves, and Vans like Sean Penn in Fast Times at Ridgmont High, even though he’d been born and raised in a land-locked farm town.

I think, unless you’re in a big city, it’s easier to dress down to match your peers than it is to break from the pack and really improve your style. I hear in the comments all the time, “People would look at me crazy if I wore ____.” But the clothes I’m suggesting – white jeans, shorts that hit above your knee, infinity scarves – aren’t really that out there. I don’t like guys in clothes that are too fashionable, so I would never recommend anything too crazy – just stylish clothes that fit well on your body. But apparently in some places, that’s simply blasphemous.

How does where you live influence your style?

Of course, you can’t help but be influenced by your city. If not culturally, then functionally. You can’t get away with a linen suit in Wisconsin in December, but in South Carolina? Sure why not. But still, I wonder: how much have you let where you live – and the people who live there – determine what you wear? Do you go along to get along? If you’re a style outsider where you live, how did you stir up the courage to wrest control of your wardrobe?

> Read more on how your hometown influences your personal style here