We may earn money or products from the companies mentioned in this post.
Even if you’re not putting the top down on your sports car and heading out for a Sunday drive, you can look the part in shoes and hats from this collection. The comfortable, slip-on driving shoes here offer modern interpretations of the classic style, featuring colorblocking and woven detailing. And the centuries-old style of the driving cap also gets an update, going beyond stalwart tweeds, with plaids and colorful woven options that eschew its English gentry connotations.
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Kangol Men’s Clery (Cafe)$48.0$25.0 -
Kangol Men’s Clery (Kelp)$395.0$25.0 -
Kangol Men’s Circuit Cap (Grey)$395.0$22.0 -
Bruno Magli Men’s Pogia Bit Driver (Light Grey)$365.0$120.0 -
Bruno Magli Men’s Pogia Bit Driver (Blue)$48.0$149.0 -
Dino Bigioni Men’s Moc Crocco Driver (Black)$48.0$125.0 -
Kangol Men’s Jacquard 507 Cap (Twill Stripe Black)$42.0$24.0 -
Kangol Men’s Jacquard 507 Cap (Twill Stripe Smoke)$195.0$24.0 -
Kangol Men’s Patched Cap (Tan)$195.0$19.0 -
Gordon Rush Men’s Davenport Driver (Tan Leather)$160.0$85.0 -
Gordon Rush Men’s Davenport Driver (navy leather)$150.0$85.0 -
Vince Camuto Men’s Rocca Woven Driver (Brown)$150.0$49.0 -
Kangol Luxe Men’s British Ripley (Burton Check)$89.0$46.0 -
Kangol Luxe Men’s British Ripley (Copley Check)$138.0$46.0 -
Kangol Luxe Men’s Neo Check Hudson (Diamond Stripe)$138.0$27.0 -
Kenneth Cole New York Men’s Sports Car Slip-On Loafer (Black)$90.0$59.0 -
Kenneth Cole New York Men’s Sports Car Slip-On Loafer (Brown)$70.0$59.0 -
Rockport Men’s Chaden Penny Driver Loafer (Tan)$70.0$50.0 -
Bailey of Hollywood Men’s Uzielli Windowpane Ivy Cap (Smoke)$90.0$30.0 -
Bailey of Hollywood Men’s Uzielli Micro Stripe Ivy Cap (Smoke)$235.0$30.0 -
Bailey of Hollywood Men’s Angelli Micro Stripe Ivy Cap (Smoke)$235.0$34.0 -
Bacco Bucci Men’s Galvan Driving Moccasin (Blue)$120.0$105.0 -
Bacco Bucci Men’s Galvan Driving Moccasin (Orange/Brown)$70.0$105.0 -
Original Penguin Men’s Zero to Sixty Loafer (Aegean Blue)$70.0$36.0 -
Bailey of Hollywood Men’s Uzielli Plaid Ivy Cap (Meadow)$158.0$30.0 -
Bailey of Hollywood Men’s Herringbone Uzielli Ivy (Sage)$158.0$29.0 -
Andrew Marc Men’s Hollis Driver (Light Grey)$98.0$64.0 -
Andrew Marc Men’s Hollis Driver (Root Beer)$51.0$64.0 -
Kenneth Cole Reaction Men’s Super-Human Driver (Taupe Suede)$51.0$49.0 -
Kangol Men’s 507 Cap (Cafe)$50.0$25.0 -
Kangol Men’s 507 Cap (Chlorine)$375.0$25.0 -
Kangol Men’s Marl Stripe 507 Cap (Putty)$375.0$25.0 -
Dino Bigioni Men’s Driver (Grey)$48.0$114.0 -
Dino Bigioni Men’s Driver (Navy)$48.0$114.0 -
Kangol Men’s Cap (Chambray)$48.0$24.0 -
Kangol Men’s Cap (Grey)$55.0$24.0 -
Kangol Men’s Cap (Navy)$43.0$24.0 -
Goorin Bros. Men’s Retainer Ivy Cap (Grey)$43.0$22.0 -
Dino Bigioni Men’s Driver (Green)$50.0$129.0 -
Dino Bigioni Men’s Driver (Orange)$50.0$129.0 -
Kangol Men’s Tropic Galaxy (Greige)$38.0$19.0 -
Kangol Men’s Tropic Galaxy (Sycamore)$195.0$19.0 -
Goorin Bros. Men’s Gaston Ivy Cap (Brown)$195.0$17.0 -
Goorin Bros. Men’s Bruce Ivy (Brown)$365.0$17.0 -
Goorin Bros. Men’s The Game Ivy (Brown)$365.0$13.0 -
Gordon Rush Men’s Finlay Driver (Brown Suede)$460.0$89.0 -
Gordon Rush Men’s Finlay Driver (Grey Suede)$460.0$89.0 -
Dino Bigioni Men’s Calfskin Driver (Black)$35.0$125.0 -
Dino Bigioni Men’s Calfskin Driver (Brown)$35.0$125.0 -
Dino Bigioni Men’s Suede Driver (Beige)$35.0$165.0 -
Dino Bigioni Men’s Suede Driver (Blue)$250.0$165.0 -
Giovannio Men’s Ivy Cap (Blue)$98.0$18.0 -
Giovannio Men’s Ivy Cap (Camel)$98.0$18.0 -
Giovannio Men’s Ivy Cap (Grey)$86.0$18.0 -
Hickey Freeman Men’s Panama Cuffley Hat (Natural)$86.0$115.0 -
Robert Graham Men’s Fetch Driver (Elmer)$205.0$44.0 -
Robert Graham Men’s Fetch Driver (Mojito)$205.0$44.0 -
Bailey of Hollywood Men’s Sienna Ivy (Brown/Grey Plaid)$205.0$34.0 -
Bailey of Hollywood Men’s Sienna Ivy (Brown/Peach Plaid)$$34.0 -
Bacco Bucci Men’s Rai 3 Tone Kilty Tie Driver (Brown/Blue)$$79.0 -
Bacco Bucci Men’s Rai 3 Tone Kilty Tie Driver (Brown/Green)$$79.0 -
Bacco Bucci Men’s Rai 3 Tone Kilty Tie Driver (Brown/Taupe)$$79.0