Brad Bennett of Well Spent Shares His Favorite Chicago Shops

Each week, Chicago-based style blogger Brad Bennett of Well Spent recommends the can't-miss quality items that won't put a strain on your wallet.


Sir & Madame

Opened in 2009 by husband-and-wife team Autumn and Brian Merritt, Sir & Madame proffers an eclectic mix of men's and women's goods from both well-known brands (Levi's Vintage) and cult ones (Brooklyn Circus). The store's real show-stealer, however, is its in-house line. Designed by the couple and produced almost entirely in Chicago, the garments offer a nice mix of heritage and streetwear styling. Or, as Autumn and Brian like to call it, urban sophistication. Standouts include slim cargo shorts, heavy flannel shirts, and some great-looking rucksacks.


Winter Session

Founded by the husband-and-wife team of Tanya Fleisher and Roy Katz, Winter Session offers a tightly edited collection of rugged bags and aprons, all handcrafted by the couple in their Chicago studio. On top of being great-looking and extremely durable, the pair's wares also boast a reduced eco-footprint, thanks to the extensive use of environmentally responsible materials. The above photo is of Roy's several-month-old Garrison Bag. And as you can see, it has only gotten better with age.


To read more about these brands, as well as see the rest of the featured businesses, check out the Go Local series on Well Spent. To view the complete photo sets from each interview, including images not posted on Well Spent, visit Nathan Michael's Tumblr The Archive.

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