The first true great American menswear brand, Brooks Brothers opened its doors in 1818 and in the 200-plus years since has defined American tailoring. Ever since the Lower Manhattan boutique began hawking suits, shirts and shoes (all entirely hand-made in the U.S.), the label gradually altered the menswear paradigm. While affluent men for decades prefered British, Italian and even French suiting, Brooks Brothers cemented America’s tailoring prowess, convincing everyone from middle-class blue collar workers to Presidents that American suits could rival any made abroad.

It was more than 80 years later when John E. Brooks (one of four brothers who collectively decided to rename their father’s business Brooks Brothers) officially introduced the “Polo” shirt. Inspired after watching a polo match and witnessing the players’ button-down collars, Brooks decided to apply the same concept to dress shirts. Unlike the modern polo shirts you are accustomed to, these “Polo” shirts are inspired in name only, and are in fact widely considered the first ever American-made Oxford shirts. Made from a thick cotton for durability and designed for casual wear, the Polo shirt became an American icon. Today, the style is available in four cuts—Soho, Milano, Madison and Traditional—and made entirely from domestically-grown Supima cotton, a far cry from the garment district mass-produced original. While many men now opt for the slimmer SoHo or Milano iterations, we feel the style simply looks better in wider cut as the original Brooks Brothers intended. Tuck the Madison into a pair of khakis and a blue blazer and you’re essentially American royalty. It’s a classic for a reason.

On the opposite end of the spectrum sits Thom Browne. An American designer with a laser-focused yet entirely modern view of the male wardrobe, Browne’s aesthetic combines tenets of rigid mid-century men's uniform with irreverent takes on new American style conventions. That said, despite his directional, gender-fluid collections and near-comical suiting proportions, Browne is arguably as obsessed with Brooks Brothers as the directional designer is with upending the rules of modern tailoring. The former designer of Brooks Brothers high-end Black Fleece line, Browne’s commitment to a three specific garments—the gray suit, the white oxford and the the black leather brogue—is a reflection of how much he reveres the building blocks of American tailoring. Of the three, by far most accessible (in terms of both price tag and wearability) is his Oxford shirt.

Made from an unusually heavyweight cotton, Thom Browne’s classic shirt features the 4-bar brand insignia on the arm, signature grosgrain ribbing on the inside placket and gussets and of the infamous exterior size tag that doubles as a brand logo. Largely inspired by Brooks Brothers’ classic Oxford, the shirt sits a comfortable medium between a relaxed and slim fit, an ode to traditional American styling. While the price tag is for many a hard pill to swallow, and the core collection almost never goes on sale, there are constantly shirts floating around on Grailed for well below retail.

With spring fast approaching and summer around the corner, it’s the perfect time to invest in some linen. The most breathable material out there is also the perfect weight and consistency for those who want to wear a button-up in the warmer months. While you might not think a linen button-up is necessarily a good investment, if you’re looking for an alternative to an endless rotation of T-shirts this summer, the linen button up is an underrated classic—think Dustin Hoffman exiting the pool in The Graduate.

For all your linen button up needs, look no further than J.Crew. The classic mid-range American label boasts one of the best shirting programs in the business, at a price that no one can touch. For its linen, J.Crew sources directly from the most respected linen mill in Ireland, Baird McNutt. It’s namesake shirt features an incredible soft handfeel, however is more reminiscent of a traditional cotton dress shirt rather than the type of static-filled hair-rising linen camping shirts your grandfather insists on wearing. With a short button-down collar and a slightly cropped hem, the shirt is designed to be worn out, and matched with a similar color pant and you have the makings of a perfect summer fit. While cut slim, we recommend sizing up for a more louche, just hopped out the ocean look. Just because it’s a pool day doesn’t give you an excuse to be sloppy.

A direct competitor with Brooks Brothers for decades, the Polo Ralph Lauren Iconic Oxford shirt was eponymous designer Ralph Lauren’s response to his juggernaut New York competitor. While it was his notorious neckties that launched the designer's label back in 1967, as the label expanded it was Lauren’s fresh take on American menswear and tailoring that propelled the business into the massive conglomerate it is today. Now over 50 years later, many of the same pieces—the polo, the tweed and herringbone blazers, the safari jacket—are still the label’s best-sellers, oxford shirts included.

Made from a midweight 100 percent cotton, the shirt features a button-down point collar, barrel cuffs and, of course, the celebrated multi-colored pony embroidery on the chest. While available in three fits—classic, custom and skinny—to suit a wide-range of tastes, we recommend the classic. With its lowered armholes, fuller sleeves and wide body, the added room creates a much more versatile silhouette, particularly for those of us who cannot fill out a slim-cut shirt. What can we say? There’s something undeniable about that embroidery. A bonafide American classic.

While American shirting is well and good, the Italians did it first. The first major Italian ready-to-wear men’s tailor to land stateside, Giorgio Armani introduced the states to the sort of classic Italian sartorial sensibilities the country is now famous for. While his collections no longer illicit the same sort of response they one did, amongst a certain set of devotees, Armani is unimpeachable.

Unlike American counterparts who prefer pique cotton or Oxfords, the Italians—and, by extension, Armani–gravitate towards more dignified, less utilitarian fabrics. For its classic shirt the label opts for poplin, an ultra-thin, lightweight 100 percent cotton perfectly suited for the light as air unstructured blazers it produces. Featuring a cut-away collar and slim (not skinny) throughout, this is the sort of shirt James Bond would reach for if he wasn’t constantly wearing Brioni.

Speaking of James Bond, the official tailor for the world’s greatest secret agent is no longer Italian. American designer Tom Ford claimed the lauded partnership back in 2008 with the release of Daniel Craig’s second Bond film, Quantum of Solace. Since then, the most reputable American designer working today has brought the enigmatic character into his all-encompassing, ever-expanding universe.

The only top tier high-fashion designer whose men’s sales outpace women, Ford is a true master of menswear. No matter the category—sportswear, denim, footwear, perfume, of course suiting—Tom Ford finds the best fabrics in order to create the most luxurious, premium version possible. For its dress shirts, the designer of course opts for poplin, made from the best cotton many can buy. With everything Ford makes, tailoring is the first and foremost concern, and his button-up shirts are exactly the same way, fitted in every sense of the world, a literal shield of cotton based armor. Featuring a cutaway collar perfect for his preferred full Windsor knotted tie, the shirt is available in both barrell and French cuff, however seeing this is a four-digit button up from the best in business, we advise you go full throttle on toss on some cuff-links. Whether it’s a wedding or your holiday party, when you wear Tom Ford, people notice.

While ostensibly a slight curveball, given that this is Grailed, we had to include at least one non-traditional choice. For those of you who are fans of the Japanese workwear aesthetic, you are already no doubt familiar with Engineered Garments. Based in New York’s garment district, the label is the only U.S.-based brand within the cult-favorite Nepenthes group. Designed by workwear obsessive Daiki Suzuki, the brand offers the most modern interpretation of utilitarian Americana through a distinctly Japanese lens. While many of its most celebrated pieces are considerably more off-kilter, its fan favorite Mandarin collar long shirts have been a menswear icon for years.

Featuring a band collar—essentially a collarless placket ending at the base of the neck—and an extended hem for layering, the shirts are made from a mid-weight cotton more closely resembling a work shirt than a true oxford. While we advise against the knee-length long shirts the brand produced circa-2012, the newer renditions which hit about mid-thigh are perfect alongside some baggy trousers and a hiking boot. Embrace your inner fashion beatnik.

We couldn’t not include menswear’s favorite brand for printed button-up shirts. Years before Prada camp collar shirts were a fashion must, Gitman Bros. was producing simple cotton button-up shirts featuring wild patterns ranging from casinos and playing cards to repeating grape motifs and woven U.S. flags. While best known for its often comedic patterns, the label is just as versed in simple oxford shirts made of high-quality U.S. cotton. Using a weighted cotton fabric, Gitman prints a bevy of patterns and textures onto its shirts, all while maintaining a level of quality and fit that fans have come to love.

While arguably passed its peak when the brand was stocked in nearly every respectable menswear boutique in the country, the label continues to release shirts guaranteed to turn heads each and every season. If you’re looking for a loud printed button-up and an unbeatable price, Gitman Bros. Vintage has you covered.

Brunello Cucinelli is hailed as the king of cashmere—and rightfully so—but he ought also be hailed as the king of effortless luxury, a look which he’s mastered since launching his eponymous label in 1978.

In some respects, Cucinelli’s Slim Fit Shirt typifies the brand: It’s simple, but well-made and subtly flattering, with a cut that hugs the body just enough, despite softer lines. It’s also one of Cucinelli’s classic pieces, a carry-over offering that, over the years, has been available in everything from classic white, blue and striped cottons to chambray to brushed cotton jersey that feels like your favorite fleece.

The Slim Fit Shirt is finished with tonal mother-of-pearl buttons, a spread collar, tri-button cuffs, and cut shorter than many dress shirts, making it a shirt that can be dressed up or down, worn with a suit or without a tie, and with jeans, whether tucked in or untucked. In short: Few luxury dress shirts are as versatile as Brunello Cucinelli’s classic Slim Fit Shirt.

It stands to reason that Comme des Garçons SHIRT would offer stellar shirting. The Comme des Garçons diffusion line, launched in 1988, is dedicated to the shirt, but also to showing a lighter side of what Comme des Garçons can be—both in terms of fabrics and color palette. It’s playful, but also polished.

While Comme des Garçons SHIRT has grown since 1988, with an offering that now includes a little bit of everything, the brand’s button-up shirts are still the standout—particularly those that feature mismatched stripes. Over the years, there have been shirts made of contrast panels, with stripes of different widths, colors, and even patterns used, turning the dress shirt into something light-hearted and irreverent.

Comme des Garçons SHIRT’s shirts tend to feature shorter collars than the others on this list, with light, almost paper-like fabrics. Combined with their eclectic stripes, these shirts are the unconventional pick for a button-up.

Founded in 1956, Kiton is one of the giants of Italian tailoring—albeit slept-on in the mainstream when compared to some of its peers, like Canali or Zegna.

Curiously, the Neapolitan tailoring house borrows its name from the Greek “chiton,” a tunic worn by aristocrats in ancient Greece, which symbolizes “classicism, quality and social distinction.” Kiton’s shirts uphold what the chiton stood for, thousands of years later.

Kiton’s attention to detail is unrivalled, but expected of the Naples-based brand: On patterned shirts, different strips of fabric are aligned so that the pattern flows unperturbed, the delicate hand-stitching is barely noticeable, and, perhaps best of all, each shirt takes 22 steps of handwork and five hours to make. A Kiton shirt is a shirt, yes, but it represents more than that. Worn, Kiton’s spread collar shirts have sleek, clean fronts that are refined but unpretentious.

While Kiton might be a tailoring house, the brand’s spread collar shirts are probably most famous in bright hues and irreverent patterns. Thus, a Kiton shirt makes a statement—both in terms of quality and look.

Founded in 1977, Drake’s prides itself on so-called “relaxed excellence” and, truth be told, that’s exactly what Drake’s offers, toeing the line between formal and relaxed: Its casual clothes are refined and put-together and their tailoring looks effortless and easy. Aimé Leon Dore has done something similar, albeit using streetwear as its base and punching up. It joined forces for the first time to release a collaborative collection for Fall/Winter 2019 and, since then, the pair’s unique blend of British-American street-wise tailoring has been a mainstay in the menswear world.

While other pieces have stolen the show, the simple cotton twill button-down shirts are worthy of a mention, with their made-in-the-U.K. craftsmanship, hefty fabric, thoughtful detailing and clean, relaxed lines. It’s a simple, almost unremarkable shirt at first glance—but it’s still stellar. After all, how many shirts are designed to look as good with grey sweatpants as with a double-breasted suit?