14 Resort Wear Pieces All Men Should Have In Their Vacation Wardrobe (2024)

It wasn’t that long ago that resortwear as a category didn’t really exist for men. We put whatever summer pieces we had in a suitcase alongside some swimming shorts, stuck a straw hat on and headed to the airport.

Thankfully we’re a more discerning bunch now and see the value in looking and feeling as good on vacation as we do at home. Lazing away the days between poolsides and restaurants requires a unique set of aesthetic qualities so we’ve spotlighted the key elements to a concise and compact holiday wardrobe.

With this set of resortwear in your carry-on, you’ll have every style box ticked, from horizontal days on the beach to the post-dinner club.

Tailored Swim Shorts

For great swim shorts inspiration, you have to travel back in time to the 50s and 60s, when the likes of Cary Grant was gracing the Cannes promenade in To Catch a Thief. Or there’s the iconic image of Dustan Hoffman reading on a pool float in The Graduate, in a similarly understated pair.

The neatly tailored style cut with a sleek leg is as chic and timeless as they come, perfect for hopping from beach to restaurant with a linen shirt without feeling underdressed. Orlebar Brown set the benchmark for modern styles when they first launched their Bulldog short in 2007, but you’ll find plenty of resortwear brands offering sleek tailored styles these days.

Terry Cloth Polo

Terry towelling is having a resurgence now – the only surprise is why it ever fell out of favour. It is woven with a loop yarn in the pick and normal chain, which means the looped ends stand up to create a super soft and very absorbent fabric.

This makes it perfect for poolside lounging, of course, but it’s just a great lightweight tactile fabric that adds a unique textural quality to your holiday outfits. While it works well in the form of polo shirts and tees, you can also find some excellent softly tailored options in the form of terry blazers by the likes of Oliver Spencer and Armor Lux.

Cuban Collar Shirt

Just like the guayabera shirt before it, the iconic Cuban collar shirt has been part of the Caribbean island’s menswear culture forever, but has only really seen a resurgence in the West in the last few years.

Now, it’s a non-negotiable piece of summer kit, thanks to that structureless collar that nonchalantly flaps open at the chest. You’ll find no shortage of lightweight cotton and linen styles (as well as some plush silk options too) that you can pair with tailored shorts and loafers for a smart vibe, or keep it relaxed with chinos and sandals.

With plain styles, go for interesting textural fabrications such as waffle knits or seersucker, whereas on the patterned side you’ll find endless options to give your seasonal wardrobe that slice of Caribbean cool.

Resort Collar Polo

While the classic two- or three-button placket polo is a very useful piece of resortwear kit, the resort collar just adds that extra bit of off-duty seasoning. The resort collar is by definition, any collar with a medium spread and no stand so that it naturally sits open and flat to the chest, rather like a bowling shirt.

The absence of buttons reaffirms the informality of it, making it ideal to wear with tailored swim shorts by day, or a pair of tapered chinos and loafers for a chic summer evening vibe. Textural styles in terry cloth and linen add an extra dimension to the polo, whereas smooth cotton jersey provides a smarter vibe.

Espadrilles

Peasant footwear since the 14th century, espadrilles were made all over the Basque region of Spain and Occitania in France. Notable for the soft canvas upper and esparto rope sole, the espadrille is still going strong after 700 odd years, reinventing itself as a comfortably chic summer shoe and a casual alternative to open-toe sandals and the like.

The aforementioned peasants would be confused to find that the modern-day espadrille has become the choice shoe for smart casual summer style, whether rolling up to the beach in a pair, or dressing down a smart evening look.

Linen Trousers

Nothing comes close to linen for lightweight breathability, which are exactly the characteristics you need in your summer trousers. Besides being very sustainable (flax crops are typically irrigated with rain water, unlike cotton crops), linen has natural slubs in the cloth which give it that subtle textural quality.

A dynamic fabric, it works well cut in wide-leg trouser styles, but is equally smart as a more tapered suit separate. Very easy to be dressed up or down with sandals or loafers respectively, opt for light-coloured neutral tones as a sophisticated backdrop for brighter resort polos, shirts and tees.

Linen Shirt

Much like the aforementioned linen trousers, the linen shirt is a key element to a sophisticated resort wardrobe. Aside from the already lauded properties of linen, this shirt swaps the stiff stand collar of its cotton cousin in favour of a much more relaxed soft roll collar.

Versatility is its forté, since you can wear it with a blazer for a smart summer look, or over your swim shorts and espadrilles for more of a bohemian beach vibe. The white option is the classic, while pastel tones and rich blues also style up well.

The Perfect Plain Tee

An invaluable part of the modern resort wardrobe, the simple white T-shirt is not to be underrated. It can hold its own as a casual poolside layer on the one hand, and chic underlayer for evening tailoring on the other.

That’s not to say any old white tee will do – seek out heavyweight cotton jersey in a relaxed fit for a more polished finish, while knitted merino tees are also a good option for wearing with tailoring in the evening (but probably not practical during the day).

Linen and linen blends are another excellent choice, but the slubby finish of linen doesn’t make it quite as clean cut as the classic cotton style.

Minimalist Sneakers

When it comes to resortwear sneakers, leave your hype kicks at home and opt for a pair of sleek minimalist pumps instead, simply because they are that much more versatile. You can wear them with shorts and a polo by day, and chinos and a linen shirt in the warm evenings.

Go for pared-back white leather styles by the likes of Uniform Standard or excellent new French brand Zespà.

Seersucker Blazer

It was a hard call between the linen blazer and the seersucker style but the latter got the nod for its laidback textural quality. The seersucker suit was born in New Orleans in 1909 at the hands of haberdasher Joseph Haspel. It takes its name from the Persian words شیر shîr and شکر shakar, literally meaning ‘milk and sugar’, from the resemblance of its smooth and rough stripes (the dimples of which allow air to flow and thus keep you cool).

When shopping for a blazer, make sure you stick to unstructured styles with a relaxed natural drape. Navy, ivory and pastel tones are all good considerations for a resort wardrobe, as well as the classic pinstripe style.

Pool Slides

The ultimate vacation slip-on, pool sliders have somehow slip-slopped their way into everyday streetwear with teenagers around the globe adopting the white-sock-and-slide vibe. That has not stopped luxury brands from proliferating this most simple of resort footwear into the menswear consciousness with logo-laced plastic forms or more sophisticated leather styles.

The Aquatic Watch

Given that most of us spend our holidays in short sleeves or at the very least with sleeves rolled up, our wrist furniture is there for all to see. What’s more, the constant dipping in and out of the pool or the sea requires a timepiece rugged enough to withstand the water, but smart enough that you don’t need to change it when dressed up in the evening.

This equation has a number of answers, depending on your budget. At the top end of the scale, Rolex’s Submariner, TAG Heuer’s Aquaracer, Omega’s Seamaster, Tudor’s Black Bay and just about anything from Panerai will give you peace of mind when in the water, while Timex’s Navi, Seiko’s Prospex and Oris’s 65 all offer excellent value.

The Sunglasses

Sunglasses are a balance of personal preference and face shape so we’re not going to say that one style is better than another, but when it comes to sophisticated resortwear, you’ll always be on the money in retro-styled frames such as Wayfarers and aviators, both of which will complement a relaxed holiday wardrobe.

Naturally, eyewear specialists have created myriad spins on the classics, but the key things to look out for are Italian acetate, quality hardwear and superior protective lenses.

Tote Bag

The final piece of the resortwear puzzle is the tote bag. Sleek and yet boasting plenty of volume for your wallet, tech and whatever else you need to traffic around, the tote is an elegantly casual bag with a simple, clean silhouette.

Canvas styles are great for the beach or the pool whereas elevated options in leather or suede add more than a touch of luxury to your look. For a more contemporary style, opt for edgier nylon totes.