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 1991 Spurs Tottenham Hotspur Gazza Matchworn 8 Hummel Shirt Trikot XlMens Pendleton Board Shirt Button Up Wool Plaid Nwot Xl Long Vintage 1940,s Made In California Rayon Hawaiian Long Sleeve Shirt RockabillyVtg Deadstock 3d Emblem Harley Davidson Shirt Nos Biker Motorcycle 1980s Vtg 50s 100% Rayon Shirt L ~ Hollywood Rouge Navy Loop Collar Rockabilly AtomicVtg 50's Penney's Foremost Sanforized Snap Front Ranch Western Shirt L NewVintage 1940s Made In California Rayon Hawaiian Shirt Sz S San Francisco SurfersVintage 40's Wwii Usn Chambray ShirtBeautiful Vintage 50's Penney's Rayon Shadow-plaid Rockabilly Shirt -m-Vtg Harley Davidson Biker Shirt Motorcycle 1980s 3d EmblemMen`s Go Barefoot Primo Hawaiian Beer Aloha Shirt Size-xl U.s.a MadeVtg 50s 60s Arrow Chevella Rayon Shadow Plaid Collar Loop Shirt Sz Medium MVtg 3d Emblem Harley Davidson Shirt Biker Motorcycle 1980sVintage Adidas West Germany Made Goalkeeper Football Shirt Size-18/lVtg Lyle & Scott Polo Shirt Indie L Large 44"chest Oldschool Oi Weller Mod KnitNew Nwt Vtg 1950s Rayon Gabardine Shirt Jac ~ Xl ~ Gene Vincent Rockabilly ElvisVtg Penguin Polo Shirt Indie L Large 42"chest Oldschool Oi Weller Mod OrangeVtg Arrow Chevella Shirt M ~ 100% Rayon Shadow Plaid ~ Rockabilly Vtg 50s Shaheen Mens Cotton Aloha Hawaiian Shirt Tiki Rockabilly Print LVtg 1950s Lancer Shirt L ~ Atomic Loop Collar S/s Rockabilly Elvis Gene VincentVtg 1950s Mr California Shirt Xl ~ 100% Rayon Rockabilly Atomic S/s Loop CollarVintage 1950s 60s Rayon Rockabilly Shirt Penneys MediumRetro Vintage 1950's Pioneer Brand Chambray Work Shirt Hipster Rockabilly LargeVtg 3d Emblem Harley Davidson Shirt Biker Motorcycle 1980sVtg 50s Hawaiian Shirt M L Pali Style Loop Collar Elvis Hand Printed RockabillyVtg 3d Emblem Harley Davidson Shirt Biker Motorcycle 1980sVtg Fred Perry Polo Shirt Indie Medium M 38"chest Mod Weller Tipped White Oi SkaVtg Stylized Emblem Oilzum Motorcycle Club Lounge Shirt Speed-parts Paterson Nj Vintage 1950's - "borges Jersey Milk" Rockabilly Gabardine Bowling Shirt - Xl -Vintage 1977-80 Spurs Tottenham Hotspur Hoddle Admiral Shirt Camiseta Trikot XsVtg Deadstock Sweatshirt Harley Davidson Shirt Motorcycle 80s Biker 3d EmblemRetro 1990s Designer Abercrombie Shirt LAdidas Vintage Tennis Polo Shirt , Jersey Lendl Size 42Vintage Buckskin Leather Suede Pullover Shirt Antler Buttons Ranger Label S/mVtg Ds Kriss Kross Shirt Rap 1990s 1980s Concert Tour Promo Public Enemy NwaFred Perry S/s Button-down Check Shirt - Xl - 46" Chest - Scooter Rockabilly ModLqqk! 1950's Rockabilly Hipster Chambray Sleeveless Hercules Work Shirt TastyVintage 40's 50's Silk Hawaiian Shirt Waikiki Matching Pockets Tourist RayonVtg 50s 60s Loop Shirt Acrylic Panel Knit Mod Pullover M ~ 40" Chest NrVtg Men's Lyle & Scott Polo Shirt Indie 46" L Large Oldschool Oi Weller Blue Vintage 1950's "town Topic" Atomic Cotton S/s Rockabilly Shirt -nos-l- NrVintage Levi's Levis Levi Jeans Western Cowboy Denim Jean Shirt Sz Mens MVtg 3d Emblem Harley Davidson Shirt Biker Motorcycle 1980sLot Of 2 Unworn Vtg 40s Style Loop Shirts Ralph Lauren Country Rayon Gab L/s MRetro Awesome Hawaiian Beach Tropical Stag Night Pattern Shirt XlYarmo Vtg Lk Blue Moleskin Mariner Work Smock Pullover Fishermans Jacket Shirt1950s Pennys Towncraft Orange Corduroy Shirt Rockabilly Car Club DragVtg 3d Emblem Harley Davidson Shirt Biker Motorcycle 1980s50s Blue/white Fleck Rayon Loop Button Daily Double Shirt L 46 Chest As IsVtg 50s 60s Cotton Print Sport Shirt Seahorse Coral Design Rockabilly Tiki - MMen`s Reyn Spooner Mele Kalikimaka Hawaiian Aloha Santa Shirt Size-xxlLot Seven Formal Shirts, Several Styles, SizesEddie Murphy "party All The Time" 80's ShirtArrow Collars & Shirts Lamp Promo/advertising PieceVtg Hawaiian Shirt By Shaheen's Honolulu Loop Collar 100% Cotton Excellent! MVtg Pendleton Shadow Plaid Wool Shirt Loop Collar Flap Pocket Xl LongVintage 30's 40's New Era Wool Gabardine Work Shirt M OldVtg H Bar C Ranchwear Western Rockabilly Shirt Long Tail Pearl Snaps 15.5-34 50s-60s Pilgrim Blue Shadow Plaid Loop Button Shirt Xl 53 ChestVtg 50s 60s Loop Shirt Acrylic Knit Mod Pullover M ~ 41" Chest Nr