Before Speedos shocked the American male into hiding in overly long and baggy swim trunks, there was a happy middle ground: the classic boardshort—that token of endless summers, Mediterranean vacations and California dreaming. Now old-school boardshorts are back and in fine form. Not too short, not too long and always in style.

That ’70s Short
Checked, 17-inch polyester boardshorts with Velcro closure, $129, by heritage brand Sundek.

British Britches
The Bulldog, a tailored, mid-length, quick-dry short, $250, by Orlebar Brown.

Back to Cali
Style 301 Originals, $61, by Birdwell Beach Britches, through South Willard.

Sucker It Up
Seersucker Volley swim shorts with UPF 50 sun protection, $44, by Lands’ End.

Island Time
The Makaha Drowner button-fly, dual-stripe trunk, $170, by Hawaiian surf shop M.Nii.