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Get ready to elevate your vacation style with our curated collection of men's vacation wear. Whether you're heading to a tropical paradise or exploring urban landscapes, Tillys has everything you need to infuse your wardrobe with the laid-back vibes of California. Discover versatile pieces that effortlessly blend comfort and style, ensuring you're prepared for any adventure. From breezy shirts perfect for beachside lounging to lightweight shorts ideal for city strolls, our selection captures the essence of relaxation and exploration. Embrace the spirit of wanderlust and make every getaway memorable with fashion that speaks to your unique style. Dive into your next destination with confidence and discover the perfect attire for unforgettable moments.
$64.99

A water-friendly sandal with anatomical arch support, 360-degree heel airbag, and built-in bottle opener.

$34.99
Now $14.97 (57% Off)

SALE!

A coral floral tile pattern swim short with a 5'' inseam, elastic waistband, and multiple pockets.

$34.99
Now $14.97 (57% Off)

SALE!

A dark coral swim short with a 5" inseam, elastic waistband, and eco-friendly recycled polyester blend.

$34.99
Now $14.99 (57% Off)

SALE!

I have like 5 pairs and I wear them almost everyday. Very comfortable...They feel like regular shorts but look nice enough to wear to a semi-formal occasion. Review Sweepstakes...

$36.99
Now $4.97 (87% Off)

SALE!

A pair of swim shorts with a water-reactive hibiscus print, elastic waistband, and 7" inseam.

$32.99
Now $24.74 (25% Off)

SALE!

RSQ Stripe Camp Button Up Shirt. Stripe print. Button front. Notch collar. Short sleeve. Lightweight and breathable material. Straight hem with side vents. 100% Rayon. Machine...

$32.99
Now $24.74 (25% Off)

SALE!

Feel is cool and light enough to wear over t shirts or alone.

$32.99
Now $18.74 (43% Off)

SALE!

RSQ Tropical Button Up Shirt. Add some tropical color to your wardrobe with a RSQ Tropical Shirt. Allover print. Button front. Camp collar. Short sleeve. 100% Rayon. Machine wash....

$34.99
Now $14.97 (57% Off)

SALE!

A stylish pair of swim shorts with an allover print, elastic waist, and multiple pockets.

$32.99
Now $18.74 (43% Off)

SALE!

RSQ Stripe Oxford Camp Shirt. This shirt features timeless stripes, adding a touch of refined charm to your wardrobe. The camp shirt design brings a casual and laid-back vibe,...

$34.99
Now $14.97 (57% Off)

SALE!

A pair of white and gold 6" shorts with elastic drawstring waist, made from 100% recycled nylon.

$36.99
Now $25.89 (30% Off)

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RSQ Big Palms Swim Shorts. Allover palm tree graphics. Elastic waistband with adjustable drawstring. Slant pockets. Back right pocket with hook-and-loop closure and woven RSQ...

$49.99
Now $29.99 (40% Off)

SALE!

Great fit and style, comfortable to wear around the house or out and about.

$36.99
Now $4.97 (87% Off)

SALE!

A pair of 7" swim shorts with an elastic waistband, available in blue and coral.

$39.99
Now $27.99 (30% Off)

SALE!

Fits well, I haven't worn them yet. Bought them for vacation....Great to wear at home or out of the house...These shorts fit great! Super comfortable to wear around the house...

$34.99
Now $14.97 (57% Off)

SALE!

A pair of red/blue striped swim shorts with elastic waist, drawstring, and multiple pockets.

$34.99
Now $14.97 (57% Off)

SALE!

A green short sleeve camp shirt with a leaf print, made from 100% polyester.

$34.99
Now $18.74 (46% Off)

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RSQ Eyelet Camp Shirt. Allover eyelet pattern. Left chest pocket. Button front. Camp collar. Short sleeve. 100% Cotton. Machine wash. Imported. | RSQ Mens Eyelet Camp Shirt

$34.99
Now $18.74 (46% Off)

SALE!

Great fit! Usually wear a small but ordered a medium for an oversize fit.

$39.99
Now $14.97 (63% Off)

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A pair of ocean-colored, quick-drying volley shorts made from recycled polyester with a modern fit.

$34.99
Now $14.97 (57% Off)

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A turquoise swim short with a 5" inseam, elastic waist, and eco-friendly recycled polyester blend.

$36.99
Now $25.89 (30% Off)

SALE!

A pair of multi-colored swim shorts featuring an allover dandelion print and stretchy polyester-cotton blend.

$36.99
Now $25.89 (30% Off)

SALE!

A pair of multi-colored swim shorts featuring an allover pattern, elastic waist, and mesh pocket bags.

$36.99
Now $25.89 (30% Off)

SALE!

RSQ Vacation Scene Swim Shorts. Allover graphics. Elastic waistband with drawstring. Slant pockets. Back right pocket with hook-and-loop closure and woven RSQ label. Mesh pocket...

Men's Vacation Wear

When it comes to leveling up your summer escapes, the right vacation wear makes all the difference—whether you’re jetting off to a tropical paradise, road-tripping down the coast, or just soaking up the sun with friends at a backyard BBQ. Men’s vacation wear is all about striking that perfect balance between comfort and style, with pieces that keep you cool and ready for whatever the day brings. Think lightweight tanks and cropped tees that let you beat the heat in style, breathable button-ups you can toss on for sunset bonfires, and shorts built for spontaneous wave breaks or weekend hangs. The vibe is effortless, but the impact is real—fresh fits that feel just as good as they look, letting you move from beach to street without missing a beat. When you’re packing for your next getaway, consider those details that make a difference: moisture-wicking fabrics for all-day comfort, relaxed silhouettes that breathe easy, and versatile layers that work for both lazy afternoons and late-night adventures. Accessories like grab-and-go bags, sunnies, and hats aren’t just about the look—they’re functional essentials that keep your vibe on point and your SPF close at hand.

Vacation wear isn’t just about what you wear, but how you wear it—and who you share those moments with. These pieces are made for anyone chasing that endless summer feeling, from the guy planning a last-minute surf trip with the crew to the one who just wants to look sharp at a rooftop hangout. They also make a solid gift for dads, brothers, or friends who are always on the go or just love a laid-back, on-trend style. Picture this: you’re heading out for a day of exploring, sliding into fresh kicks and laid-back sandals, tossing a beach towel and portable speaker into your bag, and hitting the boardwalk with confidence. Or maybe you’re gifting a set of breezy tees and boardshorts to someone who lives for weekend getaways and poolside hangs—either way, these are the must-have styles that keep up with every adventure. The right vacation wear isn’t just about looking good in the moment; it’s about creating memories that last all season long, with pieces that feel like summer, wherever you are. For even more options that blend effortless style with functionality, check out our curated collection of Cool Casual Wear For Men and discover your new favorite fits for every sun-soaked plan.