The Getup: Summer Vacation Night 2

The Getup: Summer Vacation Night 2
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 to 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

green button up short sleeve shirt

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.

Blue pull on shorts

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.

close up of geometric pattern on shorts

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 tan sneaker

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 square watch

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.

stainless steel minimalist bracelet

Fossil Stainless Steal Bracelet, $18 $65

Jewelry doesn't have to be big or flashy. Adding a small, unassuming chain bracelet next to your watch can have a rakish effect without the fuss.

Thoughts or swaps? Let's chat below!

Andrew Snavely

Andrew founded Primer in 2008 and brings 15+ years of men's style expertise. Known for his practical, relatable approach to style and self-development, he has been a recognized speaker at conferences and has styled work for top brands. Off-duty, he loves photography & editing, and enjoys road trips with his dog, Leela. Raised in rural Pennsylvania, educated in DC, and living in LA for nearly 20 years, Andrew's diverse experiences shape the relatable and real-world advice that has helped millions through Primer. On Instagram: @andrewsnavely and @primermagazine.