Jeans can get steamy in the heat, so go with a shorter option. Denim cut-offs are easy to throw on and look great with a pair of leather high-top Chucks.
Bonus: The sneakers—which tend to fade and distress—only get cooler with age.
Shorter Shorts and Boat Shoes
Shorter shorts are relaxed, so keep things low-key by pairing with casual boat shoes. From exploring a new city to actually steering a schooner, boat shoes are your best bet with 6-inch shorts.
Tailored Shorts and Oxfords
Tailored shorts are the warm-weather alternative to trousers. The clean, crisp, fitted look works best with finer shoes, such as an oxford or brogue—but skip the socks. Pair the shorts with a button-down to keep your classy-but-casual vibe in check.
Swim Shorts and Flip-Flops
Always complement swimwear with flip-flops. This leather pair is great for either poolside chilling or casual restaurant dining. Just give your feet some quality time before hitting the sand.
Long Shorts and Driving
A sleek shoe complements a longer short’s slim silhouette. Aim for neutral-colored shoes so you won’t have trouble matching shorts.
Cargo Shorts and Sandals
The age-old cargo is best worn with a sandal. The shorts have multiple pockets and a loose fit, so you should aim for the same comfort and functionality with your shoes.
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