Planning outfits for a vacation always feels like my version of a pre trip thrill.
I love those effortless looks that feel relaxed yet still give a touch of quiet luxury.
Some people love bold prints but I always find myself drawn to pieces that look polished without trying too hard.
I put together this list of refined vacation fits because I know how satisfying it is when a man’s outfit looks breezy classy and perfectly put together.
If you’re into that subtle mix of comfort and style you’re in the right place.
Breezy Beach Linen Look
This outfit is the definition of relaxed summer elegance! He’s rocking a crisp white linen long-sleeve shirt, unbuttoned just enough at the neck for that effortlessly cool vibe, with the sleeves neatly rolled up. The shirt is paired with wide-leg, slightly oversized trousers in a beautiful, earthy tan or khaki color, also likely linen or a breathable cotton blend. The whole ensemble feels incredibly light and airy, perfect for a sunny day stroll on the boardwalk or beach.
I absolutely adore this look because it showcases how simple, high-quality fabrics and a great fit can make such a refined statement. The monochromatic, neutral palette is so chic and allows the textures of the linen to really shine. The loose, flowy fit of the pants is super comfortable yet still looks incredibly stylish and flattering. It’s the perfect blend of laid-back vacation style with a touch of sophisticated class that I think looks amazing on any guy.
Mediterranean Blue and White Elegance
This outfit is giving major Riviera vibes and looks so incredibly sophisticated for a warm, seaside vacation. He’s wearing a long-sleeved shirt in a stunning rich, textured indigo or denim blue, which looks like a soft linen or a linen blend, with the sleeves casually rolled to the elbows. The shirt is perfectly contrasted with crisp white tailored trousers that are slightly cropped or rolled at the ankle. Dark brown suede loafers and classic round sunglasses complete this effortlessly chic look.
I think this combination is a winner because it’s a timeless classic that always works in a sunny climate. The contrast between the saturated blue on top and the clean white pants is so striking and instantly elevates the entire appearance. Plus, choosing breathable fabrics like linen keeps the wearer comfortable while still looking polished and refined. It’s the perfect example of dressing up for vacation without sacrificing that relaxed feeling.
Textured Knit and Linen Trousers
This outfit is the definition of quiet luxury meeting vacation comfort, which I am totally here for. He is rocking a short-sleeved top with a beautiful chunky knit texture in a warm beige or light brown shade, paired perfectly with wide-leg, high-waisted linen trousers in a pale gray or off-white color. The top is neatly tucked in, giving the whole look a tailored feel. He completes the ensemble with dark brown leather slide sandals and cool round sunglasses.
I think this look works so well because of the fantastic interplay of textures and the intentionally relaxed silhouette. The knit top adds a unique dimension that feels more interesting than a basic tee, and the flowy linen pants are the epitome of comfortable chic for warm weather. Tucking in the top defines the waist in a flattering way, and the simple, high-quality leather sandals tie the entire sophisticated, laid-back vibe together beautifully.
Boardwalk Ready in Patterned Linen
This look is absolutely perfect for a sunny day on the boardwalk or exploring a cute beach town! He’s sporting a fantastic short-sleeved button-up shirt with a cool, subtle check or gingham pattern in shades of grey and white, giving it a really fresh and airy feel. This is paired with crisp white shorts that hit above the knee, creating a clean and sharp contrast. Light-colored espadrilles, stylish sunglasses, and a simple chain necklace complete this effortlessly cool ensemble.
I adore this outfit because it perfectly balances casual comfort with refined style. The patterned linen shirt is super breathable and adds a touch of personality without being too loud, while the white shorts keep everything looking neat and summery. The espadrilles are such a chic alternative to sneakers or flip-flops for vacation, truly elevating the whole vibe. It’s a look that says “I’m on vacation, but I still have great style,” which I think is just wonderful!
Crisp White Polo and Tailored Khaki Trousers
This outfit is the picture of tropical tailoring, mixing classic pieces with resort-ready fabrics. He’s wearing a fitted, short-sleeved white knit polo shirt, often called a knitted or Cuban polo, with a stylishly deep open V-neck. This is paired with stunning high-waisted, wide-leg linen trousers in a beautiful natural khaki or oatmeal color, which are perfectly pleated and slightly cropped. Dark brown suede loafers, a sophisticated wristwatch, and round, tinted sunglasses complete this luxurious look.
I absolutely love this combination because it feels instantly elevated and incredibly flattering. The way the fitted white top contrasts with the voluminous, textured linen trousers is pure genius and creates a really lovely, balanced silhouette. It’s chic and comfortable for warm weather, and the rich brown accessories add a touch of warmth and seriousness that says this guy really knows how to dress well, even on holiday.
Earthy Linen Shirt and White Shorts
This look is the ultimate vacation uniform, combining earthy tones with light, airy comfort by the sea. He’s wearing a short-sleeved linen shirt in a gorgeous, muted taupe or light brown color, left casually unbuttoned at the top for that relaxed holiday feel. Below, he has on voluminous, pleated white linen shorts that offer a fantastic contrast and excellent breathability. The outfit is grounded with simple, classic brown leather sandals, keeping the whole vibe sophisticated yet totally easygoing.
I am completely in love with this outfit’s color palette because the light brown and crisp white look so striking and expensive together, especially against a bright blue ocean backdrop. The key to this outfit’s success is definitely the contrast in fit, where the slightly oversized shorts balance the top nicely, making it feel breezy and flattering. It proves you don’t need bright colors to look amazing on vacation, just quality fabrics and a great relaxed fit.
Knitted Polo and Classic Cream Chinos
This is such a sharp and polished look that works perfectly for an upscale resort or a sophisticated evening out on vacation. He’s wearing a short-sleeved knit polo in a beautiful, muted sage green or dusty blue color, featuring a lovely ribbed texture. This is neatly tucked into tailored, off-white or cream chinos that are cuffed at the ankle. Dark brown leather loafers and a sleek watch finish off this outfit, giving it a truly refined and gentlemanly appeal.
I really think this combination is so effective because it proves a polo shirt can be totally dressy when paired with the right trousers and fabric choices. The texture of the knitted top feels so luxurious compared to a standard pique polo, and the light color of the trousers is universally flattering and perfect for warmer weather. The dark loafers anchor the look and keep it feeling sophisticated, making it a wonderful example of relaxed class.
Navy Polo and Bright White Shorts
This outfit is the definition of nautical neatness and absolute classic vacation style. He is wearing a crisp, short-sleeved polo shirt in a deep, dark navy blue, which is a fantastic contrast against the rest of the look. The shirt is paired with bright white, relaxed-fit cotton shorts, cinched with a light brown woven belt for a touch of texture. Dark leather sandals, a wristwatch, and stylish sunglasses complete this effortless, yet very put-together, holiday outfit.
I love this simple high-contrast color scheme because navy and white together always look so clean and effortlessly sophisticated, instantly making anyone look sharper. Tucking in the polo and adding the woven belt is a small but powerful detail that instantly elevates the look from super casual to relaxed classy. The overall vibe is comfortable and cool for a beachside lunch, yet polished enough for a casual evening out, which is why it works so well.
Earth Tones Linen for Beachside Strolls
This outfit is the pinnacle of comfortable sophistication for a slightly moody beach day or early evening stroll. He’s wearing a long-sleeved linen shirt in a pale oatmeal or sandy beige color, tucked into a pair of relaxed-fit linen trousers in a deep, earthy olive green, featuring a drawstring waist. The pants are casually cuffed just above the ankle. The look is grounded with light brown suede loafers, giving it a polished, yet totally relaxed, resort feel.
I think this neutral, earthy palette is absolutely gorgeous and makes the outfit look so effortlessly chic and flattering. The pairing of the light shirt with the darker trousers is a wonderful trick to keep the focus balanced and the silhouette feeling nice and long. It’s the perfect example of how choosing breathable linen in beautiful, muted colors creates an outfit that feels luxurious and relaxed without needing a single bright hue.
Striped Tee and Flowy White Linen
This look is so dreamy and captures the essence of sophisticated island relaxation perfectly. He is wearing a simple, short-sleeved t-shirt with subtle horizontal stripes in a warm taupe and off-white color combination, giving it a nice texture. This casual top is balanced beautifully by super comfortable, wide-leg white linen trousers with a drawstring waist that look incredibly breezy. He finishes the look with textured, raffia-detailed slide sandals and cool sunglasses for a complete resort vibe.
I absolutely adore this outfit because the contrast between the fitted, textured top and the loose, flowing trousers is just stunning and so flattering. The key to its chic factor is that even though the pieces are relaxed, the all-neutral color palette and the luxurious linen fabric instantly make it look elevated. It’s the perfect example of how combining comfort and beautiful natural materials makes for the best kind of classy vacation dressing.
High Contrast Vacation Cool
This outfit is a perfect example of effortless high-contrast style, ideal for strolling through a tropical city square. He is wearing a crisp white short-sleeved shirt with a relaxed, slightly open collar, which looks like a breathable linen or cotton blend. This bright top is paired beautifully with dark charcoal grey linen trousers that have a comfortable drawstring waist. Simple, dark leather slide sandals, classic round sunglasses, and a shoulder bag complete this cool and relaxed resort look.
I really love this combination because the pairing of stark white and deep charcoal is instantly chic and always looks refined, even when the clothes are super casual. The use of linen in both pieces is key, making it feel luxurious and cool on a hot day, and the slightly loose fit of the trousers keeps the entire outfit feeling very relaxed and unpretentious. This outfit truly proves that minimal color variation can have maximum style impact, which I think is just brilliant.
Smart Floral Shirt and Dark Trousers
This outfit is such a refreshing way to wear a bold print while still looking incredibly polished and refined. He’s rocking a short-sleeved button-up shirt in a colorful floral or paisley pattern with a relaxed Cuban collar, featuring shades of purple, pink, and green. This lively top is perfectly grounded by tailored navy blue linen trousers that are cropped just above the ankle. Simple brown leather sandals and a classic wristwatch complete this stylish boardwalk look.
I absolutely adore how the sophisticated dark blue trousers instantly dress up the fun, patterned shirt, keeping the whole look from feeling too loud or casual. It’s a great example of letting one statement piece shine while using classic pieces and high-quality fabrics, like linen, to ensure the overall appearance is classy and flattering. It proves that you can embrace bright vacation prints and still look incredibly chic, which is always a style win in my book.
Linen Henley and Dark Tailored Shorts
This is the ultimate luxurious resort look, perfectly styled for watching a sunset over the water. He’s wearing a long-sleeved linen shirt in a beautiful pale beige or natural oatmeal color, featuring a stylish band collar, with the sleeves effortlessly rolled up. This light top is beautifully contrasted with structured, deep navy blue tailored shorts that hit mid-thigh. Simple brown leather slide sandals, a sophisticated watch, and classic aviator sunglasses complete this high-end, relaxed ensemble.
I love this outfit because it relies on excellent fit and classic color contrast to look incredibly chic and flattering. The light linen top is breezy and keeps him cool, while the dark, tailored shorts provide structure and a sense of formality that elevates the whole outfit beyond simple beachwear. It just shows how choosing the right fabrics and ensuring a polished fit can make shorts and a shirt look genuinely sophisticated and very appealing.
Marina Ready in Knitted Polo and White Linen
This look is absolutely perfect for a relaxed afternoon by the water, exuding that effortless European summer vibe. He’s wearing a fitted, short-sleeved knitted polo in a warm taupe or mushroom brown color, which looks so sophisticated. This top is paired with crisp white linen trousers that have a drawstring waist and are casually cuffed above the ankle. Light-colored woven espadrilles, stylish sunglasses, and a watch complete this chic marina ensemble.
I think this outfit is a total winner because the combination of textures and the neutral colors feels instantly luxurious and flattering. The knit polo adds a dressed-up element that’s much nicer than a basic tee, while the flowy linen pants ensure maximum comfort on a sunny day. Pairing it with espadrilles instead of sandals or sneakers is a fabulous styling trick that really ties the sophisticated holiday look together perfectly.
Striped Shirt and Drawstring Shorts
This look screams European coastal holiday and feels so incredibly relaxed yet classy, especially with those beautiful colorful buildings in the background. He is wearing a long-sleeved button-up shirt in a light linen or cotton blend, featuring vertical stripes in muted shades of blue, yellow, and beige, with the sleeves rolled up casually. The shirt is slightly tucked into off-white or cream drawstring shorts that have a comfortable, relaxed fit. Simple brown leather sandals and cool sunglasses complete this effortlessly chic pier-side outfit.
I just adore the easygoing elegance of this outfit, particularly how the softly striped shirt adds a beautiful visual texture without being too loud or tropical. The creamy shorts keep the entire look feeling fresh and summery, which is always flattering for a warm-weather environment. It’s the perfect combination of tailored pieces and comfortable fits, proving you can look completely refined while still being ready for a casual day of sightseeing and enjoying the sunshine.
White Linen Shirt and Grey Tailored Shorts
This is a fantastic example of balancing bright summer light with sophisticated structure for a warm evening in a tropical setting. He’s wearing a crisp white short-sleeved linen shirt, perfectly ironed but still breathable, with the sleeves neatly rolled up for a relaxed touch. This is paired with tailored shorts in a gorgeous medium grey or salt-and-pepper shade, giving a nice contrast to the bright white top. Dark brown leather loafers and a sleek watch dress up this shorts outfit beautifully.
I think this outfit is a winner because it proves that shorts can absolutely be dressed up for dinner or drinks, making it super practical for vacation. The crisp white linen is universally flattering and feels instantly refined, while the texture and tailoring of the grey shorts give them a more grown-up feel than basic cotton ones. Choosing the polished loafers over casual sandals elevates the whole look, making it chic and absolutely handsome.
Pastel Blue Trousers and White Polo
This look is absolutely giving off major Italian coastal vibes and feels so fresh and upscale for a daytime vacation outfit. He’s wearing a super clean, fitted white short-sleeve polo shirt that looks sleek and flattering. This is paired with stunning light blue or pastel sky-blue linen trousers that have a refined pleat and are neatly cuffed at the ankle. Dark brown leather loafers, sophisticated round sunglasses, and a classic watch complete this perfectly polished resort ensemble.
I am obsessed with the inclusion of the light blue trousers because they add a subtle, stylish pop of color that is still totally chic and sophisticated for warm weather. The bright white polo creates a beautiful contrast that keeps the outfit feeling crisp and clean, which is always flattering. The combination of the fitted top and the tailored, slightly looser trouser is pure genius for a relaxed but refined silhouette, making this look a ten out of ten in my book.
