Summer Vacation Night 2 · Primer

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A classy tropical evening look that looks like it costs way more than its (sale) price.

You’re a long night’s sleep and a full day of decompressing into your respite in paradise and you’re heading to the first real dinner with the people you care about. The goal is look put-together but still comfortable and casual. This outfit will work in most waterside spots, with some easy tweaks if needed:

A casual outfit featuring an olive green short-sleeve button-up shirt with white piping, paired with black textured drawstring shorts. Accessories include a rectangular Fossil watch with a brown leather strap, a silver chain bracelet, and a black leather wallet. The ensemble is completed with off-white canvas sneakers with white laces and a dark blue stripe around the sole. The outfit is marked as smart casual on a scale ranging from casual to dress.

Get the Look:
Shirt: Banana Republic
Shorts: Cotton-linen Jackquard
Sneakers: Sperry
Watch: Fossil Carraway
Bracelet: Fossil
Wallet: Bellroy Card Case

Banana Republic Luxury Touch Resort Shirt, $27.99 ~~$70~~

This relaxed fit shirt is made with jersey cotton, so while it has buttons and has a dressier effect, it’ll feel like wearing your nicest t-shirt. Plus the flat camp collar with white piping gives it a retro vibe, one of my tricks for dressing “nice” in summer.

Banana Republic Jacquard Short, $31.98 ~~$90~~

A unique pair at a discount, these pull-on shorts are made of a jacquard fabric which has a black and navy textured geometric weave.

If the pattern or drawstring isn’t what you’re looking for, a pair of charcoal chino shorts in a 7-9″ inseam will keep the outfit intentional.

For an evening look with pants, BR also has a pair of linen cotton traveler pants that would be a smart swap.

Sperry Cloud CVO Sneaker, $80

These Sperrys strike that perfect balance of classic, minimalist, and sophisticated, no easy feat for a simple canvas sneaker from a brand dating back to 1935.

If you’re looking for something more like a dressy sandal, leather huaraches are a solid choice that will fit right at home in any hot vacation spot.

Fossil Carraway Watch, $170

Rectangular watches always offer an outfit a dressier vibe, and in summer, with less layers, making use of that is strategic. We recently also featured one in our Chris Pine outfit rebuild.