22 Cool Men’s Shirts For Smart-Casual Style In 2023

Price: From $98
Sizes: S-XXXL
Customer Reviews: “Absolutely stunning, superb quality and craftsmanship.”

German luxury fashion house, Hugo Boss is renowned for their opulent range of clothing, accessories, footwear, and fragrances. Founded in 1924, and with a very controversial history (they produced Nazi uniforms during World War II), after founder Hugo Boss’ death in 1948, the company turned to men’s suits. Today, the company is a global fashion empire and produces men’s & women’s fashion lines as well as fragrances (and we promise they are no longer affiliated or condone Hitler’s actions in any way, shape, or form!).

With a huge range of casual shirts, Hugo Boss most definitely have cool shirts for men that’ll take your off-duty dressing in a new, fun direction. You’ll find high-contrast graphic prints with hardware detailing for “attitude”. They’ve got everything from short sleeve to long sleeve, linen to cotton, slim to relaxed fits.

Price: From $70
Sizes: XS-XXL
Customer Reviews: “Well made shirt that’s very breathable for the hot days, and very stylish.”

Everlane prides itself on exclusively partnering with ethical factories and using only the finest materials for their products; they call it “Radical Transparency”. Therefore, you get quality clothes that will last for years to come, with an added bonus of feeling good about supporting a company that strongly advocates for fair wages and working conditions

While Everlane is rather light on graphic shirts, they have a bunch of cool shirts in dope block colours that’ll enhance your look. Everlane’s shirts are crafted with either linen or seersucker, both extremely lightweight & breathable fabrics that’ll keep you cool in the hottest of temperatures, but are also rather textured for a cool look and feel.

Price: From $79
Sizes: XS-XXL
Customer Reviews: “High-quality shirt – Compliments on your way. If you are looking for a nice shirt, Get this one.”

Bonobos was born because founders, Andy Dunn & Brian Spaly, couldn’t find men’s pants that fit (they were either too tight or too boxy) and wanted to fix this common problem men face while shopping.

They fixed it with their not-so-secret secret: all Bonobos’ pants have a curved waistband that conforms to the natural shape of men’s waists. Bonobos then expanded into producing awesome shirts, suits, swimwear; you name a piece of men’s clothing, they do it!

Bonobos have a huge range of cool shirts for men that feature colourful prints. Extremely well-crafted, any one of Bonobos’ awesome shirts will last you for quite a long time.

Price: From $211
Sizes: 35-46
Customer Reviews: “Gorgeous fabric and print! Fantastic shirt and super quality.”

Founded in 1928, Eton has grown from the small village Ganghester in Sweden where founder Annie Petterson would sew for her friends and neighbours, into a global brand, best known for their incredible shirts. The company mantra is “made to be remembered” and this most definitely rings true when looking at their impeccable garments.

Eton’s range of casual shirts feature contemporary street style elements that are interpreted in high-end materials, and the result is effortlessly cool shirts for men. With a wide range of shirts in a variety of fits, styles, materials, colours, and prints, if you’re after a seriously stylish shirt to elevate your wardrobe, Eton is a brand you have to check out.

Price: From $125
Sizes: S-XXL
Customer Reviews: “This specific one + its navy counterpart are awesome. They’re classy, and timeless .. without being pretentious. Lightweight so as to elevate any summer style without compromising comfort. The cut is flattering; it’s not boxy and the sleeves fit right whether or not you have gym bro guns.”

World champion surfer Kelly Slater founded Outerknown in 2014; a brand rooted in environmental sustainability. Outerknown walks the fine line between function, style, & sustainability, and the result is stylish clothing that’s created with long-lasting materials and in a way that both protects our natural resources & provides fair wages to factory workers.

With a surfer at the helm, it’s no surprise that Outerknown’s range of cool shirts have a laid-back beachy aesthetic. Think tropical prints, pops of summery yellow, relaxed fits; honestly, throwing on any Outerknown shirt will make you look effortlessly cool, and ready for any adventure the weekend may throw at you.

Price: From $140
Sizes: XS-XXL
Customer Reviews: “Super soft and comfortable, true to size.”

Since its creation by David Reiss in 1971, Reiss has established a design philosophy centred on creating design-led menswear, womenswear and accessories. With an uncompromising commitment to delivering innovative and original products, Reiss fuses exceptional design, quality and value.

Reiss understands that shirts are not just reserved for the office, which is why they experiment with playful prints in laid-back fabrics as well as providing ‘classic’ shirts, so you can easily build a versatile wardrobe. If you’re after cool shirts, you’ll definitely find what you’re looking for at Reiss.

Price: From $149
Sizes: S-XL
Customer Reviews: “Will be great for my first holiday for ages.”

The joyful and free spirit of St Tropez in the 70s is forged into all Vilebrequin products, as that’s when & where the brand was founded. Best known for their men’s swim trunks, the French luxury brand produces not only swimwear but also ‘elegant vacation wear for men, women, and children.

Their range of cool shirts for men are exclusively made from linen or cotton voile for airy breathability and are impeccable elegant yet comfortable. While Vilebrequin’s shirts are specifically designed for summer getaways, these fun coloured shirts can easily be worn in your day-to-day life for a cool, fresh look.

Launched in 2013, the intention behind Frescobol Carioca was to spread the spirit of Brazil around the globe. Their collections are inspired by Brazil’s rich cultural and aesthetic diversity, such as the mosaic sidewalks of Rio’s beaches or the hypnotic rhythms of Bossa Nova… The result is well-made clothes and accessories that just ooze an exuberant vitality.

With a nice range of cool shirts for men that are predominantly crafted from either lightweight linen or supple tencel, any Frescobol Carioca shirt will give you timeless style. They have slim and relaxed fits, and prints that are, of course, inspired by Brazil culture. What’s cooler than that?

Price: From $255
Sizes: S-XXXL
Customer Reviews: “Looks stylish as well and always a pleasure to wear. This is perfect summer wardrobe stuff.”

Launched in 2013, the intention behind Frescobol Carioca was to spread the spirit of Brazil around the globe. Their collections are inspired by Brazil’s rich cultural and aesthetic diversity, such as the mosaic sidewalks of Rio’s beaches or the hypnotic rhythms of Bossa Nova… The result is well-made clothes and accessories that just ooze an exuberant vitality.

With a nice range of cool shirts for men that are predominantly crafted from either lightweight linen or supple Tencel, any Frescobol Carioca shirt will give you timeless style. They have slim and relaxed fits, and prints that are, of course, inspired by Brazilian culture. What’s cooler than that?

Price: From $125
Sizes: S-XXL
Customer Reviews: “I had ordered a shirt online. Great for my upcoming vacation!”

A lifestyle brand that emphasises comfort and versatility in all things, everything that Onia produces is crafted for ease. Clean-cut silhouettes and modern fabrics create Onia’s minimalist aesthetic, meaning Onia garments are perfect for everyday style. Founded in 2009, the brand is also passionate about fine craftsmanship and superior design; everything Onia creates is reliable, elevated, and well-crafted down to the finest detail.

And their range of cool shirts for men is no exception. Linen, cotton gauze, chambray; fabrics that are incredibly functional yet aesthetically pleasing are used exclusively, and playful yet tasteful prints in both pastel & bold colours are peppered throughout Onia’s shirt collection. If you’re after cool shirts, Onia is a brand you HAVE to consider.

Price: From $56
Sizes: XXS-XXL
Customer Reviews: “Some of the best made clothes around…. I never shop anywhere else now!”

At River Island, great design is at the heart of everything they create. Founded in 1948, the UK brand is one of the best known on the High Street, and prides itself on producing stylish yet affordable fashion. Catering to men, women, and kids, River Island also sells exquisite footwear and accessories.

With a huge range of cool shirts for men that will all give you “laid-back steez”, River Island has every kind of shirt to ensure you find the perfect one for you. From relaxed to sculpting muscle fits, from long sleeve to short, from block colours to tantalising prints; River Island is most definitely a maker of cool shirts.

Price: From $50
Sizes: XS-XXXL
Customer Reviews: “The clothes are awesome and the prices are absolutely fair for the quality that you are getting. It’s tough shopping anywhere else after coming in here.”

While known mostly for their motorbikes and motorbike gear, Deus Ex Machina believes it’s more than just a brand; it’s a culture. They have an awesome range of clothes that embody Deus Ex Machina’s core values, which are inclusiveness, authenticity, and enthusiasm.

Their range of cool shirts for men definitely takes cues from era’s gone by but also feature fresh prints and detailing, giving Deus Ex Machina’s shirts a very unique vintage-meets-postmodern aesthetic. The shirts are available in relaxed fits, and when paired with the bold graphics that are used throughout Deus Ex Machina’s collection, the result is some seriously cool shirts.

Price: From $158
Sizes: XS-XXL
Customer Reviews: “Awesome shirt and, one of the best shirt I bought in my life ….people will look at me like I’m celebrity lol…”

Iowa native Todd Snyder makes effortless everyday luxuries for the modern gentleman. Blending Savile Row’s craftsmanship with a downtown New York aesthetic, his clothing is relaxed, refined, and always impeccably tailored.

Todd Snyder also isn’t one to shy away from bold prints and colours. The brand has at least one men’s shirt in every single colour of the rainbow, and feature some of the coolest, inventive prints on the market. If you want cool shirts that’ll get heads turning, Todd Snyder is the brand for you.

Price: From $165
Sizes: XS-XXL
Customer Reviews: “I wear this shirt all the time – timeless style and great material.”

Launched in 2009, on a quiet cobblestoned street in SoHo, Saturdays NYC has since expanded into an international lifestyle brand that’s synonymous with high-quality craftsmanship, a minimalist ethos, and classic style. They have a tremendous amount of stylish t-shirts, pants, outerwear, sweaters, shorts, swimwear, and loungewear, all made from premium materials.

Ultra-modern prints are used by Saturdays NYC for their cool shirts for men, which are mostly crafted from premium cotton. Bold colours and graphic designs are abundant, and in all honesty any shirt from Saturdays NYC would instantly make anyone look cool.

Price: From $90
Sizes: XXS-XXL
Customer Reviews: “I got a printed shirt. The color is so unique. And the style is amazing. Great quality : )”

Club Monaco was founded in 1985 to create ‘better basics’; classic, effortless pieces that are well-made and elevate wardrobes. Club Monaco believes the mark of true style is experimenting thoughtfully, something they’re experts at; constantly growing and evolving their style, Club Monaco encourages their consumers to do the same.

Minimalist cool is the best way to describe Club Monaco’s range of cool shirts for men. Slim and relaxed fits in cotton and linen fabrics, with pastel colours and simple yet effective graphic prints dominate Club Monaco’s shirt collection, and no matter which one you pick, you’ll be transformed into a King of cool.

Price: From $128
Sizes: XS-XXL
Customer Reviews: “Nice fit, nice looking and very comfortable linen shirt.”

Born from a need for products without limitations, Taylor Stitch produces versatile clothing that can handle anything; chopping wood, surf sessions, snagging trout, heading to the office… Committed to building the best possible clothing while also pledging to limit their environmental impact, Taylor Stitch is one impressive brand.

Despite producing bottoms, denim, knits, and accessories, Taylor Stitch has always considered itself, at its core, a shirting company. And it’s easy to see why; their shirts are impeccably well-made and are built for the long haul. But Taylor Stitch’s shirts are also cool! They come in fun colours and prints, and will add character to any outfit.

Price: From $700
Sizes: 35-42
Customer Reviews: “Crafted with utmost attention and high quality fabric! Looks expensive, feels expensive.”

Fashion designer, Alexandre Mattiussi, founded AMI after many formative experiences with several fashion houses in Paris, Milan, and New York. Created in Paris and inspired by the French city, AMI offers stylish and comprehensive wardrobes for both men and women, and the clothing AMI creates blurs the boundaries between casual and chic.

There’s something about Parisian style that gives off a feeling of effortless elegance, and AMI most definitely captures that with it’s range of cool shirts. These shirts will easily take you from work to dinner & drinks to weekends, all while making you look incredibly stylish.

Price: From $90
Sizes: L-XL
Customer Reviews: “I honestly couldn’t rave more about the laidback but subtly refined aspects of the Island print shirt more. The fit is loose as the description states, I’d definitely size down one.”

J. Crew believes in ‘looking a million bucks, not spending it’ which is why they source the best high-quality fabrics at the most accessible prices. All of their products are classic with a modern twist, meaning you’ll always look effortlessly polished when sporting J. Crew.

With an enormous range of cool shirts for men, you have so many options with J. Crew. They’ve got every size, fit, fabric, colours, and prints you could ever dream of and will instantly give you and your wardrobe a cool laid-back look.

Price: From $50
Sizes: XS-XL
Customer Reviews: “Each and every piece of merchandise ordered has been flawless…using the faster shipping items received in a weeks time..lov’em.”

“Fashion’s best kept secret”, Boohoo Man combines cutting edge design with an affordable price tag. Pushing boundaries to bring you the latest styles but with less of a strain on your wallet, Boohoo Man’s philosophy is to not take fashion (or life) too seriously; and the result is menswear that is playful and trendy yet surprisingly affordable.

You’ll be able to easily level up your shirt game with Boohoo Man’s range, which come in long & short sleeves, and a wide variety of fabrics, fits, colours, and prints. Boohoo Man is constantly producing the latest trends, so if you want ultra-modern cool shirts that’ll add an unconventional flair to your wardrobe, Boohoo Man is the way to go.

Price: From $150
Sizes: L-XXXL
Customer Reviews: “I love the quality, and consistency of sizing. That’s always a question with an online order: will this item fit? TB fits. Always. I know my size, I don’t stray, and it always works.”

The British born tailoring brand with a twist is the luxury brand Ted Baker. Founded in 1988, Ted Baker has had a very clear, unswerving, focus on quality and attention to detail since its inception.

With Ted Baker’s range of cool shirts, you’ll be able to button up in style with the bespoke prints, fine-fitting cuts, and signature detailing featured throughout the shirt collection. You’ll find shirts that are both daring and demure in terms of design, but no matter which route you take, you’ll definitely look cool in a Ted Baker shirt.

Price: From $295
Sizes: XS-XXL
Customer Reviews: “Great colours and feel. Top quality product , great packaging and very simple to follow returns service if needed.”

Founded in 2007, London-based brand Orlebar Brown initially focused on ‘shorts you can swim in’; tailored swim shorts that can be worn on the beach or in the pool but are also smart enough to then be worn to summer dinners and drinks. However, over the years the brand has evolved to a full resort collection inspired by 1960s poolside utopia; think the Riviera or Palm Beach. The result is clothing that’s sophisticated meets fun.

Orlebar Brown’s cool shirts are exuberant and elegant; you’ll feel like you’re going on a luxurious holiday in Monte Carlo or somewhere tropical whenever you don an Orlebar Brown shirt, and what’s cooler than that? Featuring many botanical inspired prints, as well as bold block colours in both short and long sleeves, you definitely need to add an Orlebar Brown shirt to your wardrobe immediately.

Price: From $60
Sizes: S-XL
Customer Reviews: “Really great prints and thoughtful. I wouldn’t hesitate to purchase from Mango again.”

Spanish clothing company, Mango, was founded in 1984 with one goal in mind: to create clothes with “a Mediterranean essence”. Mango’s garments achieve this with their natural and contemporary styles paired with comfortable fabrics.

Mango understands that a shirt is one of the most timeless garments in a man’s closet, which is why they have a large and versatile range of cool shirts for men. They have many different cuts, fabrics, colours, and prints available, but at the end of the day, all of Mango’s shirts will keep you feeling comfortable and looking cool.