Spring in Annapolis means one thing: it's time to get outside, get on the water, and look good doing it. Whether you're browsing the docks at the Spring Sailboat Show or cheering on the midshipmen during Commissioning Week, we've got the coastal looks to keep you stylish all season long.
Spring Sailboat Show (April 24–26)
The Spring Sailboat Show is the unofficial kickoff to Annapolis sailing season — and the perfect excuse to refresh your dock-ready wardrobe.
What to wear:
- Kelly Green Dad Hat — A pop of color that says "I know my way around a marina." The Kelly Green is our most Annapolis spring shade, and it pairs perfectly with everything from a fleece to a sundress. Shop Dad Hats →
- Trucker Hats — Breathable, broken-in, and built for a day on the water. Grab one before you head to the show. Shop Trucker Hats →
- Yacht Socks — Because even your ankles deserve to celebrate sailing season. These make a great impulse buy — or a gift for the sailor in your life. Shop Yacht Socks →
Pro tip: The Sailboat Show gets crowded fast. Wear layers — Annapolis spring mornings are cool, but afternoons on the dock warm up quickly.
Commissioning Week (May 13–22)
One of Annapolis's most beloved traditions, Commissioning Week at the Naval Academy brings parades, ceremonies, and a whole lot of Navy pride to the streets of downtown.
What to wear:
- Annapolis Tees — Soft, garment-dyed, and made for a week of celebrations. Whether you're watching the Blue Angels or strolling Maryland Avenue, a classic Silopanna tee is your go-to. Shop Tees →
- Hoodies — Evening ceremonies can get breezy on the Yard. A Silopanna hoodie keeps you warm without sacrificing the coastal aesthetic. Shop Hoodies →
- Floating Keychain — Okay, it's not something you wear — but it's something every Annapolis local needs. Because keys and water don't mix. Shop Keychains →
Commissioning Week is also a beautiful time to give a gift. Know a midshipman or a proud family? Our College Send-Off Bundles make a meaningful, Annapolis-made keepsake.
Paint Annapolis (June 1–7)
As spring turns to early summer, Annapolis transforms into an open-air gallery during Paint Annapolis — one of the most unique plein air painting events on the East Coast.
What to wear:
- Kate Mancini Collab Pieces — Art meets coastal style. Our collaboration with Annapolis artist Kate Mancini brings her signature watercolor aesthetic to wearable pieces that feel right at home during a week celebrating local art. Shop the Kate Mancini Collab →
- Totes — Perfect for carrying your finds from the art sale, a picnic lunch, or your weekend farmers market haul. Shop Totes →
Paint Annapolis is a love letter to this city — and so is everything we make. Stop by the event and wear your Annapolis pride on your sleeve (literally).
Shop the Spring Edit
Ready to gear up for the season? Browse our full Spring Collection → and find your Annapolis look before the crowds hit the docks.
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