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Side of Style: Trenchermen

Wicker Park
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Trenchermen embodies everything wonderful about Wicker Park. The ambiance, the people, the location, and the food—these things all factor into what makes a a great Wicker Park restaurant.

If you’re looking for a relaxed brunch with a unique and exciting menu, then Trenchermen is your place. The vibe at Trenchermen is one to be envied by other nearby restaurants. While they spared no expense on decor, the real star of the show is the menu. Thankfully, while on paper Trenchermen might seem really fancy, in reality it’s not. The ambiance is loud and vibrant—with an array of diners.

The food at Trenchermen is fresh and inventive. Cocktails are hand crafted and delicious, which is probably why the self-proclaimed “hipsters” love this spot; they make a mean old fashioned! Read our full brunch review here.


Trenchermen’s casual-but-vibrant vibe makes dressing for the occasion easy—as really anything goes. The whole “not-trying-too-hard” look does really well, and to be honest, I try to embody that every time I dine there. Staples for Trencherman include oversized sweaters, chambray button ups, plaid shirts, and really great boots or booties. A Chelsea Boot in Wicker Park is a must. Spare no expense when it comes to comfort while dining at Trencherman, because you will be eating… a lot.

We love this oversized sweater from H&M paired with black ripped skinny jeans and some Chelsea boots from TopShop. Accessorize it with a flat top hat, bejeweled stud earrings, and a chunky plaid sweater, and you are good-to-go!

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