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    

Very Rare White 50s Penneys Towncraft Printed Corduroy Shirt Size MediumVintage Polo Ralph Lauren Stadium Bear P Wing 92 Rare Polo Usa Ski JacketVintage Ralph Lauren Polo Crest Turtleneck Sweater Mens L Snow Beach BearRare Vtg 50s Levi's Short Horn Big E Sawtooth Blue Peal Snap Western Shirt M UsaMid-century Used Catalina California Creator Hand Print Hollywood Duck ShirtVintage Mens,levis,orange Tab,small E,chambray/work Shirt, Size Medium,usedVtg 90's 1991 Harley Davidson 3d Emblem Downtown Cruise Motorcycle Biker Shirt MVintage 3d Emblem 80's Shirt Truckers Only Forging New Frontiers New/dead StockTexas A&m Corps Of Cadet Uniforms Shirt & BreechesVtg 50s Arrow Chevella Green Blue Plaid Rayon Loop Collar Shirt LVintage Michael Jordan Nike Shirt Big Face News Print Xl Gray Tag 90'sVintage Adidas Shirt LFred Perry Grey Marl Button-down Slim Fit Polo - Xl - Ska Mod Scooter Casuals Vintage 1940s Orange Rayon Palm Tree Novelty Button Down Loop Collar Shirt LVintage 1930s 40s Big Smith Work Shirt 17 Deadstock Usa Sanforized Brown Old Vtg Rare 60's Levi Strauss Small Western Cowboy Shirt Blue Grey & White StripedVintage 1950 Leopard Print Gaucho By Leifer Shirt Rockabilly M1940's 1950's Vintage Pearl Snap Embroidered Silk Western ShirtVtg 50s Arrow Chevella Shadow Plaid Rayon Loop Collar Shirt Large 16-16.5Fred Perry Utility Blue Twin Tipped Pique Polo - Xs/s - Ska Mod Scooter CasualsFred Perry Navy Cut Back Stripe Trim Pique Polo - S - Mod Ska Scooter Casuals Vintage 1992 Polo Ralph Lauren Shorts Pwing Polo Bear Snow Beach Cold WaveVintage 1950's Rayon Bowling Shirts (4) Nat Nast, Hilton Rockabilly Ohio MediumFred Perry Navy Check Button-down S/s Shirt - M/l - Ska Mod Casuals VintageFred Perry Coral Pink Tipped M1200 Pique Polo - S/m - Mod Ska Scooter CasualsRed Hot Chili Peppers 1991 Vintage Shirt Large Blood Sugar Sex MagikVtg Polo Ralph Lauren Reversible Embroidered Jacket Large Red Nylon, Navy TartanVtg True West Rockmount Ranch Wear Cowboy Western Embroidered Floral ShirtVtg 60's Jc Penney Big Mac 100% Cotton Chambray Long Sleeve Shirt Work Chore MOasis Shirt Xl Long Sleeve Rare Britpop Blur The Smiths Stone Roses MorrisseyGorilla Biscuits Vintage Xl Shirt Nyc Hardcore/punk Straight Edge Youth Of TodayFred Perry Black Twin Tipped M1200 Pique Polo - L/xl - Ska Mod Scooter CasualsDeadstock Vintage Sears Chambray Work Shirt M 15-15.5 Long Sleeve Workwear UsaFred Perry Navy Twin Tipped Pique Polo - M - Ska Mod Scooter Football CasualsFred Perry Navy Gingham Trim Button-down Slim Fit Polo - L/xl - Ska Mod ScooterVtg 90s Tommy Hilfiger Sports Big Logo Hip Hop Fleece Pullover Jacket ShirtLot Of 30 Flannel Shirts Vintage 70s Through Contemporary Cotton Plaid Work XlVtg 90's Wu Tang Clan Forever 1997 Shirt Rap Hip Hop Size Xl Tupac Biggie Lot Of 30 Flannel Shirts Vintage 70s Through Contemporary Cotton Plaid Work XlFred Perry Grey Marl Twin Tipped M1200 Pique Polo - Xl - Ska Mod Scooter CasualsVtg 90s Tommy Hilfiger Spell Out Big Logo Patch Hip Hop Style ShirtMen's 50's Vintage "gene Vincent" Style Rockabilly Knit Shirt Size S/mVintage Polo Ralph Lauren Sportsman Indian Head Chambray Work Shirt Xxl 1992Vtg Ralph Lauren Polo Sport Spell-out Pullover Windbreaker Jacket Size L Fred Perry White & Navy Check S/s Shirt - M/l - Ska Mod Scooter Casuals VintageAmazing Box Of 10 Vintage Black Tie Englsh Shirt Collars Charterhouse SchoolVintage Woolrich Plaid Wool Hunting Jacket Coat Shirt Jac Red Green & Grey Exc!Vtg 50s 60s Champion Thick Flannel Cotton Work Wear Shirt Plaid Railroad GussetsLot Of 30 Flannel Shirts Vintage 70s Through Contemporary Cotton Plaid Work XlVtg 50's Green Rayon Gabardine Pullover Gaucho Shirt.mans SmallVintage Guns N Roses ShirtRare 1970s The Rolling Stones Vintage Adidas Shirt Small S 70s Mick Jagger BlueRockmount Men's Western Wear Shirt Guitar Theme Vintage Rap Shirt "notorious B.i.g"H Bar C Mint Condition Western Shirt 16 1/2 34 Pearlized Snaps, Smiley Pocket, R90s Vintage Grateful Dead Shirts Size XlVtg 1960s Hilton Bowling Shirt Large Chainstitched Cowboy Bowladrome RockabillyVtg 50's 60's Pennleigh.cotton Flannel Plaid.shirt.mans Medium.Vintage Red Hot Chili Peppers Shirt Xl Baseball Jersey Californication 2000Vtg 70s Paper Thin Camo Camouflage Hunting Fishing Trucker Tshirt Shirt Sz M