There’s something about men’s vacation style that always catches my eye. I love the way a look can shift from laid-back to effortlessly polished with just a few thoughtful choices. Linen shirts, tailored shorts, and those timeless sunglasses always feel like a quiet nod to old money charm.
I find myself drawn to outfits that look relaxed but still carry a sense of understated luxury. It’s the kind of style that makes strolling along a seaside promenade or enjoying a quiet dinner outdoors feel like a scene from a classic film.
For me, these are the vacation looks that never try too hard yet always stand out in the best way.
Relaxed Vest and Linen Trousers
This outfit blends effortless charm with coastal sophistication. The man is wearing a beige vest layered over a crisp white shirt, rolled at the sleeves for a casual touch. His pleated linen trousers match the vest perfectly, and the dark leather sandals balance the light tones. The watch adds a polished accent while the stone wall and sea backdrop make the look feel timeless.
I love how this outfit feels both smart and breezy. It’s structured enough to look refined but still relaxed enough for a vacation stroll by the water. To me, it’s the kind of style that says you planned your outfit but not too much, and that’s what makes it so chic.
Nautical Polo and Cream Trousers
This look is pure marina elegance. A navy polo is tucked neatly into cream tailored trousers, paired with a slim brown belt and loafers. The cream sweater draped over the shoulders adds an old money touch that feels relaxed yet elevated. The yachts in the background tie it all together, giving this outfit the perfect vacation-in-the-Riviera vibe.
I adore this combination because it feels timeless and effortlessly stylish. The draped sweater instantly gives off that preppy, old money aesthetic that always feels fresh on holiday. It’s one of those outfits I’d notice instantly if someone walked by on the pier.
Linen Suit with Double-Breasted Jacket
This outfit features a classic linen suit in a soft beige tone with a double-breasted jacket. Worn with a crisp white shirt, open at the collar, and paired with tan loafers, the look is sharp yet relaxed. The pocket square adds a subtle statement, while the balcony setting with a sea view makes the whole scene picture-perfect.
I think this is one of those outfits that makes a man look instantly more elegant. Linen keeps it vacation-friendly, while the double-breasted cut adds that polished old money edge. It’s such a winning mix of refinement and ease.
Breezy Linen Shirt and Khaki Shorts
This look keeps it simple yet stylish. A white short-sleeve linen shirt is paired with fitted khaki shorts, finished off with dark leather sandals. The straw hat in hand adds a classic vacation accessory, while the natural beach backdrop gives the outfit its laid-back charm.
I find this outfit so attractive because it’s minimal but effective. The crisp shirt against the tanned skin and relaxed beach setting makes it feel like the ultimate easy vacation look. It’s carefree but never sloppy, which is what makes it stand out.
Smart Blazer with Polo and White Trousers
This outfit is the definition of polished vacation style. A navy blazer is layered over a pale pink polo, tucked neatly into white tailored trousers. The suede loafers, pocket square, and aviator sunglasses make the look even sharper. The convertible and cliffside setting complete the sophisticated vibe.
What I love about this outfit is how it balances relaxed pieces with formal touches. The polo keeps it casual, while the blazer and details give it a luxury twist. It’s that exact mix that feels so effortlessly stylish on vacation.
Classic Linen Shirt and Navy Shorts
This look leans into breezy sophistication. A light cream linen shirt is casually tucked into navy tailored shorts, paired with boat shoes. The man carries a woven tote bag with a throw blanket inside, making the outfit practical while still chic. The whitewashed house in the background enhances the resort-like feeling.
I like how wearable this outfit is. It feels approachable and easy, yet still refined. The tote bag adds character and makes it clear this isn’t just a look for show but also for living comfortably on holiday.
Pastel Polo and White Trousers
This outfit features a soft yellow polo paired with white tailored trousers and polished brown loafers. A beige sweater is casually draped over the shoulders, and round sunglasses give the final touch of sophistication. The clean village square backdrop keeps the look fresh and timeless.
I personally think this is such a charming combination. The pop of pastel feels youthful and fun, while the sweater and loafers ground it in that old money aesthetic. It’s playful yet refined, which is exactly what vacation style should be.
Crisp Linen Shirt and Tailored Shorts
This outfit nails vacation polish with ease. A classic white linen shirt is paired with tailored beige shorts, accessorized with brown loafers and a straw hat in hand. The clean fit and rolled sleeves create a breezy yet sharp look, while the cobblestone street and blooming flowers add that picture-perfect backdrop.
I love this look because it feels so effortlessly stylish. It’s simple pieces styled well, which is exactly what makes it stand out. Honestly, I’d call this the ultimate old money sightseeing uniform.
Balcony Style with Grey Shorts
This look is sleek and understated. A white short-sleeve shirt is tucked into grey tailored shorts, paired with navy loafers and a cream sweater draped casually over the shoulders. The man leans against the balcony railing, with the sea view behind him, making the outfit feel both relaxed and refined.
What I like most about this outfit is how it balances casual and smart elements. The draped sweater and loafers elevate what could be a basic shorts look, turning it into a polished vacation vibe.
Blazer and Vespa Charm
This outfit screams timeless Italian elegance. A beige blazer is worn over a crisp white shirt, styled with cream tailored trousers and brown loafers. The pocket square adds character, and the vintage Vespa completes the effortlessly stylish aesthetic.
I think this is such a dreamy look because it has that cinematic feel. It’s polished but approachable, and the Vespa prop makes it even more charming. To me, this is old money style at its most classic.
Poolside Linen Suit
This look is refined yet playful. A tan linen suit is styled with a soft pink shirt, unbuttoned at the top for a relaxed touch. Navy loafers and a patterned pocket square finish the look, while the poolside setting makes it clear this is vacation luxury done right.
I adore how this outfit combines tailored elegance with a splash of fun. The pink shirt adds personality, and the setting makes the whole vibe feel indulgent in the best way.
Monochrome Cream Perfection
This outfit leans into minimalism with maximum impact. A cream sweater is tucked into matching trousers, styled with beige loafers. The clean lines, subtle watch, and coastal balcony setting make it effortlessly sleek.
I find this outfit so refreshing. It’s proof that sometimes less is more, and when done right, it feels chic and expensive. I’d notice this instantly as a quietly confident vacation look.
Relaxed Linen and Barefoot Confidence
This outfit mixes relaxed tailoring with natural ease. A beige linen shirt is paired with cream trousers, with a sweater tied casually around the waist. Barefoot on a wooden dock, holding a bottle of wine, the vibe is laid-back luxury at its finest.
I really love how this outfit feels almost cinematic. It’s casual and unforced, yet the details still look elevated. It’s the kind of style that feels like a scene from a perfect summer evening.
Light Blue Linen and Cream Trousers
This look is fresh and polished with a coastal charm. A light blue linen shirt is tucked into slim cream trousers, styled with a braided brown belt, leather loafers, and a matching brown weekend bag. The marina backdrop with sailboats completes the refined vacation vibe.
I really like this outfit because it’s so versatile. It feels dressy without being stiff and makes walking along the pier look like a runway moment. The bag adds a chic practicality that makes it even better.
Cream Suit with Navy Shirt
This outfit is tailored perfection. A cream linen suit is paired with a navy shirt, unbuttoned at the top for relaxed elegance. Beige loafers, a patterned pocket square, and a leather document holder complete the ensemble as he strolls through charming cobblestone streets.
I think this is such a striking look. The dark navy against the cream makes it stand out, and the details add polish. It’s bold without being loud, which is exactly the kind of balance I love.
Nautical Stripe and Sunset Style
This outfit is all about yacht-ready elegance. A crisp white shirt is worn with cream chinos and black loafers, while a navy striped sweater is draped over the shoulders. The warm glow of the sunset sets the scene perfectly for this effortlessly refined style.
I love how this look captures the essence of vacation ease. The sweater drape feels so old money, and the setting makes the outfit glow even more. It’s the type of style that feels timeless in every photo.
White Shirt with Rolled Chinos
This outfit is simple yet full of charm. A white linen shirt is paired with beige chinos, barefoot at the shoreline while holding brown loafers. The rolled hems and undone buttons give the whole look a breezy, lived-in feel.
I adore this outfit because it’s proof that understated can be unforgettable. The casual beach setting makes it feel romantic and natural, like the perfect vacation evening stroll.
Seaside Café Look
This outfit is relaxed but refined. A white shirt is styled with khaki trousers, brown loafers, and a light blue sweater draped across the shoulders. The seaside café tables and potted flowers add to the easy charm of the look.
I really like this one because it’s so wearable and relatable. It feels like something you’d actually see on holiday while still having that chic old money touch. It’s approachable yet classy.
Cream Suit with Green Pocket Square
This outfit is sharp and confident. A cream tailored suit is paired with a crisp white shirt, brown loafers, and a striking green pocket square for a subtle pop of color. The ivy-covered wall behind him makes the look feel timeless and sophisticated.
I love this outfit because it shows how a small detail can change everything. That green pocket square adds personality without breaking the polished vibe. It’s such a perfect finishing touch.
Balcony Brunch Elegance
This look blends smart tailoring with relaxed ease. A cream blazer is layered over a striped blue shirt, paired with beige trousers and burgundy loafers. The pocket square and coffee cup in hand complete the refined morning vibe on a sunlit balcony.
I find this outfit so charming because it feels like an everyday luxury moment. It’s relaxed enough for brunch yet polished enough to look stylish without effort. It’s one of those looks that makes me smile instantly.
