Hat tricks

Train in vain
Head-to-toe black still works for spring, as long as it’s balanced by pastel punches. Fedora, $450, at Optimo Hats. Oliver Spencer jacket, $450, at Jake. Theory pinstriped shirt, $225, at apartment number 9. Rag and Bone tuxedo trousers, $230, at Hejfina. adidas patent leather sneakers, $135, at Barneys Co-Op. Photographed at the Kedzie El stop in Albany Park.

Untouchable style
Everyone looks more badass when wearing a cool chapeau. On Sung, left: Fedora, $450, at Optimo Hats. Trovata shirt, $138, at apartment number 9. Anzevino and Florence tie, $18; A.P.C. sharkskin suit coat, $396; and Marchand de Legumes pocket square, $8; all at Penelope’s. On Grant, right: Beaver fedora, $550, at Optimo Hats. P.A.M. jacket, $150, at Saint Alfred. Anzevino and Florence T-shirt, $39, at Penelope’s. Photographed at Marie’s Pizza, 4127 W Lawrence Ave (773-685-5030).

In the pocket
Take a cue from these guys: Remove vests from their stuffy suits, and you’re left with a hip, insouciant look. On Grant, left: vintage Borsalino hat, $225, at Silver Moon. Martin Margiela shirt, $335, at apartment number 9. Vest, $30, at H&M. Martin Margiela trousers, $405, at Scoop NYC. On Sung, right: Fedora, $450, at Optimo Hats. Paul & Joe striped shirt, $248; and Paul Smith plaid trousers, $300; both at apartment number 9. Vintage waistcoat, $80, at Silver Moon. Anzevino and Florence tie, $18, at Penelope’s. Camper shoes, $160, at City Soles. Miracle Icons necklace, $235, at Barneys Co-Op. Photographed at Marie’s Golden Cue, 3241 W Montrose Ave (773-478-2555).

Counter culture
Stripes don’t have to be in-your-face to make a statement. Let them peek out from under a button-down shirt. Miracle Icons necklace, $235; Barneys Co-Op jacket, $310; both at Barneys Co-Op. Nice Collective striped shirt, $110; You Must Create shirt, $120; both at Hejfina. Montecristi hat, $850, at Optimo Hats. Photographed at Susie’s Drive Thru, 4126 W Montrose Ave (773-283-6544).

Shake it up
Seersucker and straw hats aren’t just for old fogies anymore; the Geritol generation would never rock them with bold, look-at-me sneakers or skull-and-crossbone neckties. On Grant, left: Milan hat, $350, at Optimo Hats. Jacket, $60, at H&M. Rag & Bone tuxedo trousers, $230; Corpus T-shirt, $55; both at Hejfina. Nike Court Forces, $70, at Niketown. On Sung, right: Nicole Fahri seersucker trousers, $268; Lee Allison tie, $90; both at apartment number 9. Anzevino and Florence shirt, $69, at Penelope’s. Barneys Co-Op jacket, $310, at Barneys Co-Op. Vintage Borsalino hat, $225, at Silver Moon. Cloak shoes, $535, at Jake. Photographed at Susie’s Drive Thru.