What to Wear for a Summer Regatta

From the Gotland Runt to casual yacht club weekends, summer sailing season is as much about style as it is about the sea. Wondering what to wear to a regatta? We’ve curated five refined, wearable men’s outfits designed to help you look the part—whether you're racing, relaxing, or raising a glass at the harbor bar. Think Riviera polish meets Swedish archipelago ease.

We’ve assembled five looks that carry you from morning harbor strolls to evening dinners and everything in between. Anchored in tailoring, comfort, and subtle flair, these outfits are your guide to dressing well for Gotland Runt, the Eton Archipelago Race—or simply a very well-dressed weekend by the sea.

Preppy Regatta Dinner

This is your “I-just-came-from-the-helm” dinner look. Crisp, club-appropriate, and lightly nautical without tipping into cosplay. The classic Oxford gives polish, while the white trousers and navy layer nod to tradition. Finish with loafers and a spritz of sea salt spray in your hair if you didn’t earn it naturally.

The Deck Stroller

Ideal for dockside coffee runs and leisurely inspections of other people’s boats. A soft, well-fitted polo keeps things sharp without trying too hard. Tailored shorts and retro-leaning sneakers make this feel like a nod to the '60s Riviera. The bandana? Optional, but undeniably confident.

Archipelago Swim & Lounge

For those between-race hours—or entire days—spent horizontal by the water. This look is your stylish permission slip to lounge, dip, repeat. Wear the linen shirt open, sleeves rolled, and treat the espadrilles like barefoot’s better-dressed cousin. Bonus points if your swim shorts double as tailored trunks.

Summer Night Layering

When the sun dips behind Sandhamn’s pine-lined horizon (or any horizon for that matter), this is what you reach for. Lightweight knits and tonal layering meet transitional function. Think warm enough to stay out late, polished enough for that unplanned nightcap. If you’re layering correctly, you’ll look better with each piece you peel off.

A summer regatta isn’t about overthinking your outfit. It’s about letting style glide alongside substance. These looks? They do the work—so you can focus on navigating the social seas.

See you on deck.