The definition of a good shirt depends on where and how it will be worn. If you're getting in a round of golf with some friends, then a Burberry, Lacoste, or Izod polo shirt is probably perfect. Office attire may demand a handsome Thom Browne oxford or perhaps a tasteful print from Emporio Armani. And if you are just hanging around the house on the weekend, a vintage plaid or two-tone from Campus or McGregor is probably as formal as you want to get.

That said, when it comes to a good dress shirt, there are a few things to look for. Turndown collars should have removable bones, the yoke or back of the shirt at the neck should be split (this is a particularly costly detail if a pattern needs to be matched), and the sleeve should be pleated where it meets the cuff. Cotton is the favored fabric, and weaving styles include poplin, Oxford, and pinpoint, which is a combination of the two.

For the best suits, well-dressed Englishmen head to London’s Savile Row. For the best shirts, Jermyn Street is their destination. Turnbull & Asser requires a minimum order of six shirts, with a delivery time of 12 weeks. New & Lingwood is famous for its brightly striped shirts. And while the tailors at Harvie & Hudson can make you a jacket and pair of pants, they are best known for their shirts.

That’s the formal stuff. For casual wear, perhaps the most collectible category of vintage men’s shirt is the Hawaiian shirt, particularly those made during the 1930s, ’40s, and ’50s. Many were made of cold rayon, so-called for its cool, silky feel against the skin, but lots of Hawaiian shirts came in a more textural crepe de chine rayon, as well as cotton and silk.

Patterns ranged from vibrantly colored tropical floral prints to scenes of Hawaii to abstract, monochromatic designs. Vertical patterns that create a border at the buttons and buttonholes are especially prized, and collectible labels include Surfrider Sportswear, Catalina, Kahanamoku, Kamehameha, Kahala, Hale Hawaii, Royal Hawaiian, Duke of Hollywood, and (wait for it) J.C. Penney.

Rockabilly shirts from the second half of the Hawaiian shirt’s heyday are also sought after. Look for two-tone button-ups or pullovers, bowling shirts with the names of strangers stitched above the breast, or shirts in Mid-century Modern atomic-style prints.

Western shirts are cousins to rockabilly. Levi’s signature denim shirt from 1954 was called the Sawtooth, so named because of the jagged shape of the pocket flaps on the front of the shirt. With all dues respect to Levi’s, though, Rockmount Ranch Wear of Denver had been making similar shirts for years...

In fact, what Levi’s is to jeans, Rockmount is to the cowboy shirt. In addition to Sawtooth pockets, Rockmount also makes shirts with Quarter Horse pocket flaps and flapless pockets called Smiles, which should give you an idea of the shape. Rockmount is known also for the snaps on its shirts, which are mother-of-pearl in circles or diamonds, as well as its incredibly detailed embroidered shirts.

Like Levi’s, many Rockmount products are made out of denim. Chambray, which has that similarly blue, denim look, is also a favorite, as is gabardine and even traditional patterns and weaves such as tattersall. Other Western-style shirt makers include Wrangler and Dickies.

Of course some shirts are hot among collectors because they are favored by fashionistas. Robert Graham shirts, which have been around for barely a decade, took off when contestants wore them on “American Idol.” Shirts by motorcycle giant Harley-Davidson and venerable retailer Abercrombie & Fitch are always in demand, as are shirts by relative upstarts like Ed Hardy and Lucky Brand.

About our sources | Got something to add?

▼ Expand to read the full article ▼

Best of the Web (“Hall of Fame”)

The Black Tie Guide

The Black Tie Guide

Peter Marshall became an authority on formalwear out of necessity — he needed a tux to wear on the maiden transat… [read review or visit site]

Fashion Columbia Study Collection

Fashion Columbia Study Collection

The Fashion Columbia Study Collection (FCSC) is the digital home of the Columbia College Chicago’s fashion archiv… [read review or visit site]

Most watched eBay auctions    

No For An Answer Rare Shirt Sxe Uc Schism Insted Chain Of Strength Yot Ralph Lauren Polo Xl Navy Blue 1989 Sweater Americana Flag Wool Hand Knit BearVintage 1950's Albert Shaheen Of Honolulu 7up Surfing Print Hawaiian ShirtVintage 1930 1940 Austin Reed Summit Mens Collarless Tunic Grandad Cotton Shirt Vintage Long French Linen Worker Farmer Shirt Smock Pintucks Homespun Flax TopVintage 1940’s Palm Beach Goodall “beach Cloth” Shirt By Jayson! MVintage Polo Ralph Lauren Usa Superman Jacket L Hi Tech Ski Bear 1992 93 P WingVintage French Linen Cotton Blue White Stripe Worker Farmer Shirt Jacket Coat Vintage Penney's Towncraft Rayon Chevella Shirt Size M Red/gray Shadow PlaidFred Perry Port Marl Twin Tipped M3600 Pique Polo - L - Mod Ska Scooter CasualsFred Perry Light Blue Polka Dot Trim Penny Collar Slim Fit Polo - M - Ska ModVtg 1988 Deadstock Adidas Olympic Shirt Sz Xl Made In Usa Hip Hop Rap Nos NwtLot Of 70 Vintage Western Shirts Pearl Snaps Rockabilly 80s 90s Contemp M Lg Xl Fred Perry Laurel Wreath White Twin Tipped Polo - M - Ska Mod Scooter CasualsVintage 70's Levi's Orange Tab Size Large Chambray Button Front Work ShirtVintage Rare Polo Ralph Lauren Collection Tennis Shirts Excellent Condition Sz LFred Perry Hunting Green Twin Tipped Polo - L - Mod Ska Scooter Football CasualsVintage Western Shirt H Bar C Fringe Stage Shirt Poly Rockabilly Mens Xl BlackFred Perry Black Tipped Knitted Slim Fit Polo - M - Scooter Mod Casuals SkaFred X Drake's Navy Paisley Print Twin Tipped Polo - S - Mod Ska Scooter CasualsVintage Long French Linen Worker Farmer Shirt Smock Antique Homespun Flax TopFred Perry Navy Stripe Collar Pique Polo - M - Ska Mod Scooter Football Casuals Vintage Western Shirt H Bar C Fringe Stage Shirt Poly Rockabilly Mens Sz Xl RedVintage Levi Big E Denim Late 60's Early 70's Shirt Jacket Leisure Mod Men's MFred Perry Navy Button-down Tartan Trim Slim Fit Polo - L - Ska Mod ScooterLacoste White & Blue Check Button-down Shirt - L - Size 39 - Mod Ska ScooterVintage Harley-davidson Motorcycle Get Your Pipes Cleaned Biker Chopper ShirtPolo Sport Sweater Ralph Lauren Bear Sweater Mens Large V-neck Golf Bear CottonLot Of 40 Vintage 70s Shirts Disco Triumph Kennington Jantzen Dimension WranglerVtg 1992 Ren And Stimpy Shirt Mtv Nickelodeon Cartoon 90sVintage Gianni Versace Silk Shirt Baroque Medusa Head Atelier L/xl/xxl 90s Rare!Ralph Lauren Polo Vintage 1989 Patchwork Sweater Flag Wool Hand Knit Bear CrestVintage Levi's Western Shirt 70s Disco Snap Front Leisure Jacket Cowboy Mens 38Fred Perry Limited Edition Ice Blue Twin Tipped Polo - M - Ska Mod Scooter RareVintage 1930s Shirt All Over Cartoon Print Music Tune Togs MediumKiller Lvc 1950's Bowling Shirt Vintage Repro Levis Rockabilly Vintage Doughboys Shirt Mega City Four Teenage Fanclub Crush All Systems Go PunkGrillo's Pickles Shirt Lockin Out Mental Boston Hardcore Ssd Sxe Slapshot BaneLacoste Oxford Light Blue Button-down Shirt - Xxl - Size 45 - Mod Ska ScooterUnworn Mint Vintage 1980's Kenny Rogers Country Dress Shirt Elvis Swing Dance LPretty Green Black Long Sleeve Twin Tipped Polo - S - Mod Ska Scooter CasualsNeurosis Hand And Sickles Long Sleeve Original Shirt Large Super Rare Sub Pop Shirt Tad Dickless Gwar The Dwarves. Vintage Original NirvanaFred Perry Navy Twin Tipped Pique' Polo - S - Mod Ska Scooter Casuals VintageVtg 50s Super-cord Pinwale Corduroy Loop Collar Shirt Two Tone Mod Rockabilly LVintage 50's Alfred's Acetate Striped Ban Lon Rat Pack Rockabilly Shirt LargeVintage 1980's Harley Davidson 3d Emblem Why Ride Anything Else Shirt!Fred Perry Black Twin Tipped Pique' Polo - S - Mod Ska Scooter Vintage CasualsVintage 1988 80s Iron Maiden Can I Play With Madness Sleeveless ShirtVintage Southern Classics Embroidered Roses Western Rockabilly Snap Shirt XlBruce Springsteen True Vintage Born In The Usa Shirt 1984 Never WornVtg 50's Ashfield By Duke Of Hollywood Rayon Camel Desert Aloha Hawaiian Shirt M1950s Vintage Gene Elvis Rockabilly Multi Colored Striped Summer Shirt Vlv LVintage Washington Dee-cee Western Wear Denim Chambray Work Shirt Size 16-32Vintage Club Babyhead Shirt WhiteLot Of 9 Vintage Chambray Work Shirts Embroidery Golf Dragon Flowers Usa Vtg 70s3d Emblem Harley-davidson 50/50 Vintage Screamin Eagle Motorcycle Biker ShirtVintage Donegal Rockabilly Rayon Gab Shirt Men's Medium Loop CollarVtg Lion Of Troy Shirt Tux Tuxedo Ruffled 70s Prom Formal Wear Mens Sz 17/33 New3d Emblem Harley-davidson 50/50 Follow Nobody Vintage Motorcycle Shirt Medium