Summer in Chicago means hitting Lake Michigan and a scramble to find a friend of a friend with a boat. I’ve always said Chicago is a bipolar city: it’s cold and barren during the short days of winter and during those long summer days, humid and bustling. These are the months we live for. The months that we brute the fearful Chicago winters for. It’s Summertime Chi.
Here’s a casual summer day look that I’ll be rocking often this summer. A summer must for me since middle school has been my Sperry Topsiders. These classic preppy shoes have been such a staple because they’re a perfect summer shoe. They’re comfortable, breathable, and stylish. The style I’m wearing is the Men’s Gold Cup Authentic Original Chevre Boat Shoe. The shoes are lined with soft lambskin and have the iconic preppy two-eye eyelets with rawhide laces. The Functional 360º Lacing System means that the shoelaces loop all the way around the shoes and can be pulled to tighten for a great fit. My top is a linen shirt from Faherty Brand and my khaki shorts are a new favorite fit from Topman (I have them in khaki and navy).
If you don’t have a friend with a boat, here are some rental companies that I’ve either used in the past or recommend here in Chicago:
- Chicago Boat Rentals
- Chicago Nautical Boat Rentals
- or take a ride on the H.R.H Lola!
Shop the look here:
Here are a few more styles from Sperry’s new arrivals this summer that I’m lovin’:
Photography by Wes Taylor