124 Cumberland St., 647-352-4433
For anyone who goes to the beach to wear a swimsuit—and not, necessarily, to swim—Mara Hoffman is the first name in look-at-me apparel. The New York–based designer accessorizes her va-va-voom suits with snatches of pattern that are a little bit Amazon, a little bit Caribbean, and a whole lot of fun. $245–$275.
The Narwhal Boutique
8 Price St., 647-351-5011
This Summerhill boutique knows a thing or two about sexy, stocking a healthy selection of barely-there swimwear. The best: a solid-coloured two-piece, the frivolously frilly Beach Glow Rafaella by Eberjey. It’s also comfortable, if that matters at all. $190.
12 Trinity St., 416-413-1410
The New York–based Relwen does relaxed American cool better than any company out there, and there’s no single piece of clothing more relaxed, American or cool than board shorts. These are cut slim for a modern look, but still hang long enough that they’re unfussy and easy to wear. $208.
26 Bellair St., 416-920-2281
Board shorts aren’t for everybody. Specifically: not for Cary Grant, Robert Redford, or any of the men who’ve ever played James Bond. These trunks by Onia are cut classically—that means short—and suitable for a yacht deck cocktail. $100.