Written by 9:03 am Economics

How To Nail Poolside Cool (Without Falling Back On A Tank And Flip Flops)

The effortless way to style the best days of summer.

When the sun is at its hottest, it can be easy to reach for the tank top and flip flops and be done with it. After all, functionality over style can be just as important during a heatwave as it would be in a blizzard. 

But if you ask us, the long days of summer offer up some of the best opportunities to show off your best looks. And the truth is: there are plenty of ways to dress classy rather than lazily, even in the midst of a heat wave.

So if you’re heading to a pool party, out on vacation, or for a day at the beach, there’s no excuse not to put as much effort into your look as you would for social occasions throughout the rest of the year. So when it comes to nailing your waterside look this summer, don’t put so much focus on keeping cool that looking cool goes out the window as a result. 

Here are our top tips for pulling off a high summer look in style. And the best part? You can mix and match these 16 pieces and your ‘fit will always be on point.

On top

A classic t-shirt

Everlane / See our picks for the 11 Best Pocket T-shirts

When the sun is beating down, it can be tempting to grab the loosest top in your wardrobe. But trust us: a neatly fitting tee not only looks better, but it will feel better too. Opt for an absorbent natural fabric like 100% cotton and you won’t feel the sweat like you would in a baggy tee that doesn’t offer any wicking benefits. It’s the perfect casual poolside look that’s casual, but not too casual.

A polo shirt

image of a man wearing a coral red short sleeve polo shirt

The Tie Bar

The open neckline of a polo shirt allows some room for the breeze to cool you down, especially if regular tees aren’t your thing. As well as extra skin exposure, the collared neckline of a polo feels slightly preppy, which makes it a perfect waterside look that’s reminiscent of a yacht club vibe. This smarter angle also makes it an easy choice to throw on when you’re leaving the pool or beach for lunch or cocktails.

The tipped style of this bright polo from The Tie Bar is one of our recommendations if you don’t like the uniform-ish look of the common pique polo.

Popover shirt

image of a man wearing a short sleeve grey shirt

Club Monaco

A short-sleeved pull-over shirt is the natural step up from a polo. The benefits of a T-shirt but the formality of a button up shirt combined, the popover offers light, breezy fabric options like linen without the formal feel of buttons. And if you pick a classic plain or striped style, it can even work perfectly with your swim shorts when it’s time to hit the bar.

Printed shirt

dockers camp collar shirt


We’re here for the resurgence that printed shirts have seen. The classic summer style is ideal for the beach and can be a great way to feed some personality into your laid-back look. Wear it open if you’re confident, or buttoned up half way for a breezy Riviera look. Just be sure to go for big, bold patterns that feel contemporary compared to smaller, more formal patterns.

On the bottom

Tailored swim trunks

man wearing green swim trunks

Amazon / Upgrade: Vuori

An obvious poolside essential, there is no swimming without swim shorts (officially, at least). But picking the perfect pair isn’t just about what fits. If you find a pair of swims shorts that actually looks good – by which we mean isn’t too tight or too baggy, falls in the high- to mid-thigh area, and is comfy in the waistband. When it comes to prints, patterns, and colors, you’re free to experiment with whatever you like best.


image of close up of grey linen shorts

Target / Upgrade: SuitSupply

If you’re enjoying time by the water but not in it, cotton or linen shorts are the perfect option. Go for a similar length to your swim shorts, but with a slightly smarter edge like a button-up waistband and rolled leg. Simply paying attention to the cut and fit of your shorts can do some serious heavy lifting when it comes to elevating your look – and it’s no less comfy than your baggy at-home pair.

Linen pants

linen pants

28 Palms / Upgrade: Alex Crane

Shorts not your thing? If you only want to wear your swimmers in the sea and need a longer option that’s just as comfy for lounge time, look no further than linen pants. Slim- or straight-fitting pairs feel contemporary and cool, and can easily be paired with a T-shirt or button up shirt depending on how formal the occasion is. For extra comfort, pick a pair with a drawstring waistband.

White pants

image of a man wearing white pants and blue shirt


Date night by the water, lakeside weddings, or other formal summer events can call for something a little smarter than loose linen. Enter: white pants. Bringing this summery shade into your smart wardrobe instantly makes it feel less stuffy when the sun is out. Opt for linen-blends or cotton for sweat-wicking comfort, and pick a slim- or straight-leg cut for a comfy fit that still looks refined. You could even wear these to pool parties with a printed shirt or polo if your usual look is more elevated than most.

On your feet

Leather sandals

image of a person wearing birkenstock style sandals


We know flip flops are comfy, but honestly: how often do they look good? In the past decade, the rise of fashionable sandals means there’s no shortage of smart and stylish options out there for men – and they all come without the uncomfortable and (mostly) unattractive toe thong and distracting clip-clopping noise. We love a leather strap pair with a sturdy footbed. And the best part is, they’re just as easy to pair with smarter pants as they are with your swim shorts.

White sneakers


Box-fresh sneakers look especially great under the glare of the sun, which is why we like to get our brand new white pair out during this season. Break them in during summer, and you won’t mind so much if they begin to get mucky in fall and winter. Minimal sneakers have become so ubiquitous (in a good way) that they can easily be paired with formal looks as well as your throw-on beach outfit. And for extra comfort, opt for a canvas slip-on pair.


image of grey espadrilles shoes

Soludos / Amazon

Sandals aren’t for everyone. But if you want the same comfort and breathability without having your toes on show, try espadrilles. This traditional Spanish style is designed for wearability, so they can face the sand and sea without losing any of their refined look. Just slip them on, and enjoy a day of comfort and style.

To complete your look


Persol / Amazon

Sunglasses don’t just look great, they’re good for your health. So unless you’re looking forward to getting cataracts, there’s no good excuse to be seen without a pair this summer. From classic aviators and wayfarer styles to bolder contemporary frames, the beauty of sunglasses is that you only need one pair in your arsenal. Dedicate some time to finding a style that perfectly suits your face shape, and they’ll last you for years to come.

Tote bag

image of a white canvas tote bag

Orelebar Brown / Budget alternative

For days by the pool or ocean, you’ll need a practical bag that’s comfy to carry and fits all your things. And no, we’re not talking about your battered old backpack. A large tote can easily carry your towel, camera, book, sandals, and other beach essentials. And when the time comes to move on to dinner or drinks, you won’t mind carrying this refined style into the bar.


image of a man wearing a pink hoodie sweatshirt and a grey ball cap


Baseball caps are no longer reserved for athletes and teenagers. Now, just about anyone can pull off this cool, protective accessory with style. From plain designs in classic colors to quirky slogans, there are no shortage of caps on the market – so if you’re heading out in the sun, keep your head and face shaded in this newly-revived casual look.


Seiko field watch

Seiko / The Best Watches Under $200

An underrated summer accessory, the watch works extra hard when you’re by the water and don’t want to risk water damage to your phone. When the weather is hot, we often want to wear as little as possible. So if you’re looking for a way to add simple accessories to your summer look, the watch is an easy and timeless (in the style sense, at least) option that won’t minimize your comfort, but will maximize your style.

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