How To Do Nantucket Right
I was lucky enough to have been flown up to Nantucket on Memorial Day weekend for the annual Figawi sail boat race by SquadUP. Really it’s an elaborate excuse to be around tons of other preps and get really really drunk in a nice setting. And get drunk we did.
Outside of all the drinking the island was chock full of preppy clothes, from the Chubbies shorts on the guys and statement necklaces on the girls to the Sperry TopSiders, color pants, and button downs on both. There also were many preppy staple stores such as Lily Pulitzer and Jack Wills to One Orange, who hosted us on Sunday for an intimate cocktail party in the alleyway behind their store. They even had special Tucker Blair x Figawi needlepoint embroidered items like belts, coasters, and flasks.
Across the way Chubbies shorts opened up a popup shop just in case you needed a last minute short shorts fix. It was great that they did that but it seemed like tons of guys up there already had theirs, including myself. I made sure to especially bring my American flag Chubbies because what Memorial Day outfit wouldn’t be complete without a little patriotism.
If you’re looking to go to Nantucket in the future make sure you bring these things:
- Sperry TopSiders
- Colored pants
- Button down dress shirts, preferably Oxford cloth
- Chubbies shorts or shorts above your knees
- Vineyard Vines tees (VV is a local fave)
- Croakies for your sunglasses
- Bathing suit, mid calf length (2xist makes some great swim trunks like this)
- Baseball cap - TuckerNuck is a local fave
- A weekender bag - Hudson Sutler makes some really great ones tailored to the prep set
- Oh yeah, and a coozie
If you can’t find some of this stuff the island will be sure to have it, especially the Vineyard Vines store. Go there and pick up a pink whale coozie. Everyone loved mine when I broke it out to drink.
Here’s to the next vacation!