The Ultimate Men’s Vacation Style Guide: The Best Resort Style Picks for 2025
Planning a beach vacation or tropical getaway this year? Whether you’re heading to Cabo, the Amalfi Coast, or the Caribbean, vacation style is just as important for the guys as it is for the girls. This guide is packed with men’s style outfit inspiration, packing tips, and the best men’s resortwear picks for 2025 — from stylish swim trunks to laid-back linen looks, and everything inbetween. Let’s get your suitcase looking as sharp as your destination.
What to Wear on a Beach Vacation: Men’s Edition
When you’re on island time, your outfits should feel just as breezy, relaxed, effortless, and elevated as you do. Men’s vacation fashion in 2025 is all about cool comfort with an eye for detail and something special — think: high-end textures, fun prints, breathable fabrics, and a polished take on casual-cool.
Best Men’s Vacation Shirts
Lightweight button-downs and printed short-sleeves are a must. Look for resort shirts that go from beach to bar with ease.
Top picks:
Clean, crisp, ultra-soft linens
There’s nothing more effortlessly chic than a crisp linen shirt on vacation. It’s breathable, lightweight, and instantly elevates your look — whether you’re headed to a beachside brunch or a sunset dinner. I’d recommend whites, sand tones, or soft pastel corals and blues. I love the look when my husband leaves a linen unbuttoned over his swim trunks for that classic cool-guy-vibe. (I also love to steal his linens as beach cover ups on vacation!!!)
The Best Men’s Swim Trunks
The cornerstone of any tropical packing list. Choose quick-dry fabric, bold prints, and flattering lengths (you know you best, a 4.5 inseam swim trunk can be ultra-flattering, or go with a more classic 6-6.5 inch inseam swim trunk for a relaxed-but-chic vibe)
My Favorite Picks:
Tip: Pack at least two pairs so you always have a dry one on hand.
What to Wear to Dinner on Vacation (Men’s Style Tips)
Dinner on vacation is your time to shine. Think coastal cocktail attire: linen pants, elevated polos, and resort button-downs.
Our picks:
- Linen sets (pair with loafers or espadrilles)
- White jeans + lightweight shirt + leather sandals
- A blazer over a hawaiian for fancier resort dinners (this is my FAVORITE guy look!)
What to wear while traveling
A chic relaxed jogger like this, paired with a comfy tee, is the perfect travel look.
Best Vacation Shoes for Men
The best travel shoes for men are versatile, comfortable, and stylish enough for any setting.
Pack these:
- Leather slides or espadrilles (for dinner)
- Flip flops or sandals (for the beach)
- White sneakers (for exploring the town)
Men’s Resort Accessories
Don’t forget the details:
The Best Men’s Resortwear Brands
Looking for where to shop for a guy or as a guy? These are our go-to brands for men’s tropical vacation outfits:
- Kenny Flowers
- Rails
- Orlebar Brown
- Alex Crane (sustainable linen)
- Faherty
What to Pack for a Beach Vacation: Jetset’s Men’s Packing Checklist
✅ 3-4 swim trunks
✅ 3-4 resort shirts (mix of prints & solids)
✅ 3-4 dinner outfits
✅ 1 pair of white sneakers for travel & gym days
✅ 1 pair of sandals or slides and 1 pair of nicer loafers for resort dinners
✅ Hat, sunglasses, and sunscreen
Final Thoughts
Men’s resortwear is having a major moment, and it’s easier than ever to pack like a pro for your travels. Whether you’re looking for honeymoon men’s style inspo, guys’ golf trip looks, a sailing trip with friends, or just a fun adult spring break, your outfits should feel chic, effortless, and fun!
Now tell us — which destination are you styling for next?
