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WHAT TO WEAR: Weekend Wear

It’s the weekend! Summer weekends are the best, especially if you’re living in one of the busiest and most happening cities in the world. Chicago’s most anticipated summer events include Taste of Chicago, the Pride Parade and Lollapalooza. Add the countless number of local markets, outdoor concerts, street fairs, marathons and food festivals to the list, and you’re sure to be booked every weekend until Labor Day.

This weekender sports a solid V-neck T-shirt and casual twill shorts. T-shirts and shorts are key elements to a foolproof weekend outfit for both men and women. The simple combo can be easily played up by mixing different textures, prints or colors depending on your personal style. This Fashionisto chooses to pair his outfit with classic leather boat shoes—the ultimate summer men’s shoe. His look is completed with a pair of mirrored aviators and a leather strap watch. Combining comfort and style, this Fashionisto masters weekend wear in a look that can be taken from an afternoon sail to a backyard soirée.

Whether you’re a foodie, a music junkie, a shopaholic or an art lover, you’ll surely be able to enjoy one of Chicago’s summer happenings. Personally, I can’t wait to attend the city’s Dose Market, an event that celebrates the best of Chicago’s food and fashion community.

No matter which event you’re attending this weekend, make sure to consider both comfort and style when selecting your outfit. Happy summer!

One Simple Change: It’s date night! Swap your T-shirt for a light, textured sweater to dress up your look and keep you toasty on chilly summer date nights.