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    

Vintage Wrangler Denim Sanforized Western Button Up Shirt Blue Bell Big E PearlVintage 1950s 50s Big Mac Cotton Blue Denim Work Shirt New Old Stock NosRare Vtg 1960's Wrangler Denim Western Shirt Blue Bell Sanforized Size 15 1/2Vintage 50s Mid-century Old Kentucky Well Made Sanforized Work Shirt Size 17 NipVtg Bnwt Deadstock Og Nos Fila Bj Borg Settanta Tennis Shirt Us36 80s Casuals SmVintage 1950's "towncraft" Chevella-type Shadow Plaid Rockabilly Shirt -s/m- NrVintage 1950's Pink Black Plaid Wool Loop Collar Rockabilly Monterey Shirt SVtg Bnwt Deadstock Og Nos Fila Bj Borg Settanta Tennis Shirt Us42 80s Casuals LVintage 1950's "arrow Chevella" Shadow Plaid Rayon Rockabilly Shirt -l- NrVintage 50s Rayon Bowling Shirt Rockabilly Native American Indian Sz 15Vtg 50s Style Xl Black Rayon Embroidered Bowling Shirt Ichaban 10 Strikes!!Vintage 1950's Surf'n Sand Hawaiian Shirt-jac 46" Chest Alfred Shaheen Aloha!Versace Silk Shirt & H&m Xl Brand New From Fashion Week Superb Art! Masterpiece!Vintage 1970s 70s Levi's Denim Jeans Western Snap Work Shirt New Old Stock NosVintage Polo Ralph Lauren Bear 92 93 Shirt Pwing SnowbeachDirty Rotten Imbeciles "crossover" Era Tour Shirt 1986 Black Flag Slayer VenomVintage 1950s Novelty International Print Cotton Rockabilly Shirt New Old StockVintage 1950's "h Bar C" El Dorado Western Gabardine Rockabilly Shirt Large NrOriginal Issue Vtg 1984 Iron Maiden Aces High Tour Sleeveless Low Shirt CutoffVintage 1950's "h Bar C" Rosemead Western Gabardine Rockabilly Shirt Large 16.5Burberry London Burberrys Check Great Shirt Sz M Medium Rare Logo ExpensiveVtg 80s Ac/dc Who Made Who Concert Tour Levi Denim Jean Jacket Backpatch Shirt TKenzo Homme Great Shirt Designer Sz 16.5 Expensive & Rare CottonVintage Obituary Slowly We Rot Tour Shirt Sepultura Sodom Slayer Bathory VenomVtg 60s 70s Lee Denim Blue Jean Cowboy Western Shirt Pearl Snaps Fred Perry Check Green & Red L/s Cotton Shirt - Xxl - Ska Mod Scooter TerracesNew - Vintage 1960's British Bri Nylon White Shirt By Delamare - Size 17" CollarVtg 40s 50s Mens Beige Crepe Rayon Rockabilly Shirt L Vlv Loop Collar CaliforniaVtg 70's Daber Nude Afro Woman Girl Polyester Retro Disco Big Collar Shirt Small1930's Chin Strap Work Shirt Wool Plaid Rough Condition Pull OverFred Perry Check S/s Cotton Shirt - Xxl - Ska Mod Scooter TerracesVintage 1950's Pali Handprint Hawaiian Shirt M 44" Chest In Steele Book Aloha!Lot Of 50 Vintage Western Shirts Pearl Snaps Rockabilly 70s 80s 90s Large XlVtg Levis Blue Denim Chambray Western Shirt M Orange Tag Levi's Vintage 80's Red Western Pearl Button Denim Shirt,size L/44Superdry Japan Co. Mens Shirt Heavy Denim Sz M Designer Cotton Logo Medium Vintage Buffalo Plaid Loop Collar 50's Mint Pendleton Virgin Wool Board Shirt LVintage Western Shirt H Bar C 70s Pearl Snap Polyester Smiley Pockets Navy WhiteVintage 1950s 50s Shell Gas Station Green Denim Work Shirt Washington Dee CeeVintage Versus By Gianni Versace Silk Shirt Size 48 Made In Italy60's Vintage Pabst Pbr Shirt Sz L!Vintage 1960s 60s Big Mac Cotton Blue Denim Work Shirt New Old Stock NosVtg 50s Chambray Work Shirt Washington Dee Cee- W/gussets- Distressed. 15 1/2Vtg Lot Slayer Iron Maiden Metallica Motorhead Rock Metal Concert Tour T-shirtsVintage Led Zeppelin, Jean Jacket. Rare Patches! Concert ShirtVintage 1950's No Label Crepe Rayon L46" Chest Great Print Hawaiian Shirt Aloha!Vintage Woolrich Lumberjack Plaid Mens Wool Shirt Jacket Sz L/xlVintage 50s H Bar C Ranchwear Western Shirt Square Dance Cowboy Long SleeveVintage 50's H Bar C Ranchwear Western Shirt Square Dance Cowboy Long Sleeve50s Arrow Contour Tailored Rayon Chevella Loop Collar Shirt Rockabilly Size M Vtg Bowling-shirt King-louie Chain Stitch Foot Printer Fresno Ca Green L #11Lot Of 26 Flannel Shirts Vintage & Modern 70s Though Current Plaid Med Large XlVintage 1960's Davinci Da Vinci Cardigan Style Sweater Jacket Shirt Sz Mens LVintage Adidas 3 Stripe 80s Polo Usa Red White Blue Stripes Cotton Sz S ShirtVintage 60's Penneys Ranchcraft Denim Western ShirtVintage Green Black Plaid Lumberjack Wool Hunting Shirt Jacket Coat Large To XlVintage Pendleton 2011 Beach Boys 50'th Anniversary Wool Shirt1950s Elvis Pink Rockabilly Shirt With Tri Colored Crowns L VlvVtg Deadstock 40's Sanforized Work Shirt L/xlVtg 70s Brooks Brothers Navy White Real Madras S/s Shirt 16 Large Usa Ivy League