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 Rayon Gabardine Shirt Marlboro Green 40s 50s Medium Flap Pockets LoopVtg Lot 16 Nirvana, Pearl Jam, Pink Floyd, Van Halen Rock Concert Tour T-shirtsVintage Bowling Shirt Great Print On Back Bob Vintage Japan Made Vintage 60s MedVintage Original Circle Jerks Tour Shirt Off!black Flag Dead Kennedys PunkVintage Rayon Shirt Made In California Usa Rockabilly Nos LargeVintage 1986 Grateful Dead Summer Tour Concert ShirtVtg Lot 16 Ac/dc, Kiss, Iron Maiden, Metallica, Metal Rock Concert Tour T-shirtsVintage Shirt 50s Button Down Collar Polka Dots Cotton Rockabilly Deadstock AsisVintage 1950's Atomic Zig Zag Flannel Rockabilly Shirt -xl- NrLot Of 50 Vintage Western Shirts Pearl Snaps Rockabilly 70s 80s 90s Large XlVintage 1950's Pink & Grey Flannel L/s Rockabilly Shirt -s- NrRare 50`s Levi`s Sawtooth Denim Shirt Original No Lvc (gripper Brand Snaps)Vintage 50s California Ranchwear Gabardine Embroidered Pearl Western Shirt 14.5Adidas Trefoil Vintage Xl Shirt Trikot Camiseta Maglia Made In TurkeyVintage 1950's Atomic Print Rockabilly Shirt -xl- NrVintage Levis Dark Blue Denim Look Western Shirt Saddleman Pearl Snap Vtg 70s Mens Vtg 90s Polo Sport Ralph Lauren Printed Logos Rugby Shirt Large BlackLot Of 5 Vintage 70s Denim Chambray Work Shirt Embroidered Novelty Flapper SportVintage 1950's Style Ukulele/hibiscus Print Rayon Hawaiian Shirt Sz M/l HipsterJack Wills Mens Stripes Shirt Top Great Cotton Rare Awesome Sz Xl Ex Large Vgc[my2]vintage Bic Mac Jcpenney Butterfly Embroidered Western Chambray Shirt N.o.s. 1944 Ww-2 Military Wool Uniform Shirts Olive Drab Green Long Sleeve.w/tagLot Of 25 Vintage 70s Shirts Disco Groovy Campus Van Heusen Hippie Hipster PolyVintage Alice In Chains Shirt Tour Layne Staley Authentic Retro 1993 Rooster TVintage Shirt 50s Contrast Collar Cotton Atomic Swirls Dapper Deadstock Asis NosVintage Holiday Sportswear Shirt Western Lounge Wear Hipster Rayon LargeLot Of 5 Vintage - Jimmy'z, Gotcha & Quiksilver - Shorts & ShirtsVintage Type 1939 World's Fair Print Levi's Lvc Limited Shirt -l- NrLot Of 14 Vintage Shirts Deadstock Button Front Vintage 70s Perm Press Arrow UsaVtg Mens Penney's Sanforized Button Front Long Sleeve Denim Style Blue Shirt1960-70s Custom Casual Vintage Photo Shirt Dirt Bike RacerVtg 1950's Dee Cee Sawtooth Black Cotton Diamond Pearl Snapped Western Shirt MdVintage 1950's Pirate Ships In A Bottle Rayon Hawaiian Shirt -m- NrVintage 1950's Gradation Stripe L/s Rockabilly Shirt -m- NrVtg 60s 70s Belair Black And White Disco Short Sleeve Mens Shirt LHandsome Westman Panhandle Slim Western Cowboy Shirt MVtg Mens Penney's Sanforized Button Front Long Sleeve Denim Style Blue ShirtVtg 1950's Hawaiian Shirt Hale Kala Surf Hibiscus Floral Paradise L Lg Lrg RareGaastra Great Shirt Top Expensive Rare Stripes Sailing Sz Xxl ExpensiveTommy Hilfiger Shirt Vintage Retro 80s Size M/m On Label Superb ConditionVintage Men's Jams World Rayon Colorful Hawaiian Shirt - XlVintage Garfinckles Linen Striped Hippie Festival Muscle Woodstock Shirt Tunic MVtg 60s 70s Multi Color Dotted Disco Short Sleeve Mens Shirt LVtg 70s-80s Burnt Yellow Ruffled Delton Tux Tuxedo Men’s Shirt Brown Trim Sz 15 Vintage Shirt 50s Button Down Collar Cotton Novelty Prt Boys Chubby Cheeks ToysVintage 1950's Cartoon Whiskey Fish Rockabilly Hawaiian Shirt -drunk Bum- L- NrVintage Judas Priest Painkiller Tour Shirt Xl 1990 Rare OriginalLot Of 2 Vtg Langlitz Leathers T Shirts 1990s Motorcycle JacketVintage 3d Emblem Harley Davidson Follow The Spirit Motorcycle Pueblo Shirt Sz LMen's Vintage Yellow White Plaid Shadow Enro Top Loop 50s Shirt - MVintage Bud Berma Plaid Western Mens Medium Shirt M/s Short SleeveVintage 40's Rayon Hawaiian ShirtVintage 1950's Atomic Pattern Cotton L/s Sanforized Rockabilly Shirt -s- NrRare All Over Print Van Halen Balance Tour Shirt 1995 Supreme Bape Vintage Vtg1950s Shaheen-like Joss Sticks Made In Hawaii Metallic Gold Hawaiian Shirt AlohaVtg 60s 70s Blue Lace Disco Long Sleeve Mens Shirt MLarry Mahan Vintage Rocky Mountain High Hippie Cowboy Western ShirtVintage 70's Joel California Polyester Button Up Groovy Hippie Shirt Sz Mens MVtg 60s 70s Spire Brown Disco Short Sleeve Texured 3d Mens Shirt MVintage Shirt 50s Pullover Henley Surfer Laceup Neck Cotton Oxford Beach As Is