In Chicago, great men’s stores have traditionally been few and far between. But lately some fresh openings have reversed that trend. The new Jack Spade on Oak Street features the prep-school, smart-aleck style that has made the line famous. Reasons to visit include the signature bags, designed for men who don’t want a stodgy briefcase but are too old or professional for the beat-up college backpack. Messenger bags, briefcases, and duffel bags are available in canvas (from $195) and leather (from $345). The shop also carries shirts in cozy flannel or striped cotton (from $135), merino sweaters ($225), and Chicago-winter-worthy outerwear, such as the hooded Kentz coat ($695) and the Scottish mackintosh coat ($995), made from water-resistant rubberized cloth.

Jack Spade products are suited for the man who doesn’t take himself too seriously. “Our apparel and bags are well made and functional, but there’s room to have a personality, too,” says Chad Buri, the New York–based head of marketing. Accessories include basic cork wallets (from $85) and ties (from $95) but also an impish wool hat with an eye patch ($95), gloves with “hero” and “zero” written on the knuckles ($95), and small business cards that read “Stop Talking” ($11). And Jack can’t let Kate have all the fun with stationery. A foolproof Every Card You Need stationery box ($68) contains cards for Valentine’s Day, birthdays, and so on, to eliminate those last-minute trips to the drugstore.

The bright shop, across the street from the standalone Kate Spade store, has a vintage, lived-in feel and Chicago-found furnishings. (Kate Spade and her husband, Andy, who created the Jack Spade line, are no longer affiliated with their brands. Both lines are now owned by Liz Claiborne.) The same brownstone building also houses locally owned men’s shop George Greene—a purveyor of high-end European fashion—and newcomer Shrine, which is bedecked with all manner of dapper accessories. The shopping trip that every man supposedly makes once a year? It just got a little easier.

GO 47 E. Oak St.; 312-915-0315, jackspade.com
Finds Bags created in smooth mill leather ($155 to $395)

Photography: Courtesy of vendors