Just because you’re taking a holiday doesn’t mean you should take a vacation from looking good. Good casual resort attire is flattering, comfortable, and, best of all, easy.
I’ve said it once; I’ve said it a thousand times. To master resort casual attire is to master casual menswear in general. This is especially so when it comes to summer and spring casual.
And I know what some of you might be thinking. The point of casualwear is to be relaxed. The idea of mastering it as an art? Tiresome. Intimidating maybe. No worries! It’s less of an art and more of an elementary school equation.
And, of course, there are always ways to incorporate it into any guy’s personal style. You’ll see that achieving a cosmopolitan, worldly, but entirely unstuffy off-duty Bond look is as easy as pie.
Or, in this case, as easy as a margarita on the beach.
What Is Resort Casual Attire? A Quick Primer
Casual resort wear is a style of relaxed dress that one would wear during a summer resort. This means it accommodates the practical needs and dress codes of that vacation experience.
It may be a large hotel with amenities and programming, a cruise ship, or a community of businesses around a main lodging facility.
Yes, there are winter resorts as well. However, those often revolve around a sport, like skiing. The attire there is more technical than the more common summer resort situations. And, it’s a different topic of dress completely.
So today, we’re focusing on soft, breathable fabrics, warm weather shorts and pants, loose but still clean-lined pieces, and well-ventilated slip-on shoes. Basically, you want clothes you can wear for days on the beach, on an island, on a boat, or even on a safari.
Breathable Fabrics To Consider
You want summer fabrics that allow air to flow through the garment. This means looser, lighter weaves, often lighter colors, and sweat-wicking qualities.
- Poplin
- Light jersey
- Seersucker
- Chambray
- Linen
- Bamboo
- Silk
- Hemp
- Certain synthetics like rayon, micromodal, and tech fabrics
So, basically, go for versions of your basics in these fabrics.
Don’t bring a wool blazer in a dark neutral like navy. Bring a linen blazer in lighter neutral colors like cream and light slate.
Instead of denim, go for chambray. So on.
Resort Casual Dress Code: A Range
Let’s talk about the resort casual dress code. Even within this category, there’s a range.
If you’re at a work-sponsored resort, colleagues may be around. You’ll still need to be polished.
Or maybe you just want to look good even when you’re extremely comfortable.
Here are the most basic casual pieces. Then, I’ll show you how to level it up from there if you want to.
The Most Casual Resort Attire: Basics
Since these pieces are at the extreme end of casual, it’s important to ensure a proper fit. Again, summer holiday attire can be looser for comfort purposes. Just make sure the shoulders of your shirts are well-fitted and that the lines are clean and mostly straight.
Crewneck T-shirt
You might even go for a scoop neck, if that’s your style. Go for light cotton blends, like poplin. Light colors fit a warm-weather vibe best. Ideally, you want a shirt with UPF protection.
Hawaiian Shirt
Hawaiin shirts are celebratory, fun, and comfortable.
Good ones are usually made of silk, which means they’re also great for your skin.
Casual Pants
Don’t bring heavy jeans or even traditional wool dress pants. I sometimes wear my dress pants casually, but they’re too restrictive at a resort.
Instead, you want light linen pants or even lightly woven cotton chino-style trousers. They’re highly casual but give a cosmopolitan aesthetic.
White jeans are also a resort staple that can be worn casually or with a suit jacket.
Shorts
Find yourself some light linen or bamboo shorts (which you can often find in sets) or some classic chino shorts.
Cargo shorts are a good option if they’re well-fitted and fall above the knee.
Sneakers
Go for light, breathable canvas
Boat Shoes
These are good at the beach, by the beach, and on a boat. And hey, resorts are the only places you can actually wear boat shoes with a blazer.
Hat
You have to protect yourself from the sun. If you’re a baseball cap guy, a vintage one might add more character than any old hat you find at the sporting goods store.
Pool Wear
Bring a pair of swim shorts, a singlet, and flip-flops. However, make sure to only sport these items when you’re poolside or beachside.
Garments to Level up Your Casual Outfit
Alright, let’s take it to the next level. Here are some items you can pair with the pieces above if you want to look just a bit more polished.
The outcome will still be casual, and putting the outfit together will be just as easy. However, these pieces add structure that mimics dressiness without actually being dressy.
Polo Shirt
If you’re anywhere near a golf course, you’ll want a polo shirt. For style purposes, though, you might try a knit polo with a less structured collar.
Or, perhaps try an open-weave button-up polo. You can wear it open with a shirt or singlet underneath.
Since you’re likely going for a lighter, less structured construction or even a looser fit, I highly recommend cinched hems. This adds a flattering structure to the arms and waist while maintaining comfort.
Collared Shirts
In general, going for a collared shirt versus a non-collared one will level up your casual outfit.
A linen button-up can be worn with shorts, linen trousers, or even a suit jacket. If you find a bamboo or silk blend, it has a nice sheen to it that adds character without loudness.
Camp collar shirts are perfect for lounging by the pool and are completely unstuffy. They’re like a more sophisticated aloha shirt.
Popover Shirt
A popover has the silhouette of a rugby shirt but is looser, softer, and more relaxed looking.
Madras Shorts
Madras is a preppy staple and is most natural in warm weather holiday settings.
If you’re so bold to wear them, they go well with polos, blazers, boat shoes, and loafers.
Dress Shorts
Dress shorts are my secret weapon in making a casual summer outfit look a bit more chic.
They were popularized by Thom Browne and are basically just dress pants cut above your knee. They pair beautifully with polos and light, linen button-ups.
Seersucker Suit
Now, I don’t have it in me to wear a full seersucker suit unless it’s a dress code requirement. However, you can use the separates in interesting ways within a casual dress code.
Seersucker pants with an untucked linen button-up, for example. Or a monochrome polo and shorts combination with a seersucker jacket over it.
Light Safari Shirt
A lightly woven safari shirt is the summer counterpart to a shirt jacket. It looks worldly, the pockets are convenient, and they’re nice to have on windier summer nights.
Classic Straw Hat
A straw trilby hat, straw fedora, boater hat, or panama hat are classier options over a regular baseball cap. And they can be worn in a T-shirt and shorts or a summer suit.
Espadrilles
Espadrilles have a European vibe to them. They’re comfortable and breathable. Opting for them over
Leather Sandals
If you’re not a flip-flop guy, a premium pair of leather sandals is a good way to go.
A singlet with an open camp collar shirt, swim shorts, and a pair of full-grain leather sandals? Way classier than just swim shorts and flip flops.
Driving Moc
They may not be as nautical as boat shoes, but they’re a dressier style of slip-on that’s still fully informal.
As an added plus, driving mocs give you good traction.
Using Formal Pieces Casually
Did you know you can wear dressier pieces in casual contexts? They add a level of distinct sophistication.
Just don’t pair any of these with each other. Add them to a completed outfit using the above toolboxes, and you’re good to go.
- Blazer or sport coat
- Hard-soled leather loafers
- Velvet slippers, particularly ones with nautical accents
- Pocket square
The Athletic Clothes Conundrum
Some people will say to avoid workout clothes, and I understand why. But athleisure has come a long way since the days of baggy sweatpants and velour track jackets.
These days, brands make polos, shirt jackets, and button-ups in performance materials. These are good options for days you’ll be doing a lot of physical activity.
Slim navy joggers, a matching shirt, and white
Conclusion: Don’t Forget to Experiment a Bit
When it comes to resort casual attire, I recommend going for that loud pattern you thought you could never do. Or go for that slightly feminine color that makes you a bit insecure.
After all, it’s casual wear. And it’s casual wear in a completely different world than your everyday life! Have as much fun with your clothes as you do with the resort activities.
If you’re heading to a resort, what are some clothes you plan on wearing? Do you ever incorporate dressier items into your casual vacation clothing rotation? Let me know in the comments!
