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    

Vtg 50s Big Mac Salt & Pepper Chambay Work Shirt Sz M Sanforized Denim Jc PenneyVtg 50's Sears Hercules Chambay Work Shirt Zipper Front Sz M Sanforized Denim80s Vtg Paper Thin 50/50 Converse All Star Ringer Shirt Sz Small Made In Usa NosVintage Chambray Shirt Us Navy Army Wwii 50s Gussets Denim Large 16 1/2Levis Big E Shorthorn Western Shirt Size MMen's Vintage 1950's Rockabilly Short Sleeve Shirts - Lot Of 4 - "as Is" Medium5 Vintage Ween Shirts (all Men's Xl)Lot Of 8 Vintage 70s Denim Chambray Work Shirts Embroidered Patch Novelty Kitsch80s Vtg Paper Thin 50/50 Converse All Star Heathered Ringer Shirt Sz S Usa MadeVtg Mens Leather Biker Jacket Sz L 44 Large Brown Western Trucker Slim Shirt XlVintage Levis Big E Denim Family Western Slant Pocket Shirt 40s Rare Men's Vintage 1950's Rockabilly Rayon Print Shirt With Cotton Knit Detail LgLot Of 4 70s 80s Vtg Paper Thin Tri Blend T Shirts Sz L/xl Rayon Camel Small OgLot Of 18 Vintage 50s 60s Rockabilly Shirts Loop Collars Flap Pockets Atomic GabFabulous Vintage Checkered Flag Firestone Uniform Shirt With EmblemLot Of 4 Nos Paper Thin Tri Blend T Shirts Sz Small By Russell 80s Vtg Rayon New80s Vtg Converse 3/4 Sleeve Raglan Baseball Shirt Sz S Made In Usa All Star Nwot 1950s Short Sleeve Geometric, Atomic Design Shirt, Rockabilly 1950s Gabardine Gaucho Shirt, Rockabilly, Rocknroll, Pullover Vintage 1950's 'campus' Top-stitching Detail Short Sleeve Shirt*size MediumSuper Clean Vintage 1940's Denim Shirt Washington Dee Cee Good Size Work WearMen's 1940s Rayon Novelty Print Pajama Top And Bottom, Shirt, Sleeping Dog PrintVintage 50s 60s Shirt Cotton Reverse Weave Sport Jersey Deadstock Unisex 71Vintage Original 1960s Us Army Tiger Stripe Combat Shirt! Vietnam War EraVintag 1985 Dio Sacred Heart Concert Tour Shirt Ronnie James Rock Band Concert Vtg 50s Gabardine Shirt Waistband Two Tone Rockabilly Campus Wow MHuge Lot 1900's Antique Mens Shirt Collars Arrow (7) Antique Ties (30) Cuffs EtcVintage Big Mac Penneys Denim Chambray Button Work Shirt Sanforized Nos TagsVintage 1950's Penny's Towncraft Shirt*size Large 16,16-1/2Vtg Fred Perry Polo Shirt Indie Xl 46"chest Mod Weller Oi Ska Slim Fit BlueAdidas Vintage Football Shirt Red Soccer Jersey 1970's Rare Original Retro (l) Vintage 40s-50s Rayon Bowling ShirtMen`s Vintage 60`s Bernard Rockabilly Two Tone Shirt Size-m ?Vtg 50s Loop Shirt Rayon Fleck Gene Vincent Gradation Stripe Xl 52" ChestVintage 1940s 50s Atomic California Pink Gabardine Loop Collar Shirt RockabillyVtg Fred Perry Polo Shirt Indie Large Xl 48"chest Oldschool Oi Weller Mod AgryleVintage Wrangler Blue Bell Flannel Western Denim Shirt Rockabilly Mint Sz.mSuper Rare Original Vintage Marilyn Manson Satanic Army Longsleeve ShirtVintage Hale Hawaii Hawaiian Shirt Loop Collar TikiMen`s Vintage C.c.filson Co Plaid Purple/black Work Shirt Size-l Usa MadeVintage 1960's Men's Button-up Shirt / Nos ~ UnwornVintage Bell Helmets Button Up Shirt 1960s Motorcycle Club Outlaw Biker Colors Vintage 60s Arrow Chevella Shadow Plaid Rayon Long Sleeve Button Shirt Mens LVintage Big Mac Chambray Embroidered Cowboy Western Rockabilly Work Shirt Snap MLot Of 2 New Nos Mip Men's Ever-fresh Vintage 50's Shirts Plaid Rockabilly M Vtg 60s Primo Beer Polo Shirt * Hawaiian Holiday * Aloha Brew Mens Rare : MdMen's Vintage 1970's White Ruffled Tuxedo Shirts - Lot Of 3 - L/xlVtg Fred Perry Polo Shirt Indie L Large 43"chest Brasil 2010 Special Edition ModVintage 90s Does 70s Embroidered Western Men’s Shirt Sz XlVintage 1950's 'essley' Flap Pocket/loop Collar Shirt*size Medium 15/15-1/2Funky Peacock Polyester 70's Disco Shirt M Robert Firenze Sy DevoreLot Of Men's 70's Disco Hippie Shirts Mens Sz L. Polyester Funky BVtg Fred Perry Polo Shirt Indie L Large 44"chest Oldschool Oi Weller Mod BlueVintage Denim Shirt Western Pearl Snaps Small -xs Work Blue Usa Unisex Big MacVtg 1940's Bercktowne California Multi-color Striped Rayon Gabardine Shirt LargeVtg 50s 60s Shirt Gaucho Jac Panel Front Knit Gene Vincent M 45" ChestVintage 50's Rockabilly Elvis Rayon Shirt Prince Jac By "campus" Tri-color-m Vintage 1950s 1960s H Bar C Ranchwear Western Shirt Dan River Fancy Cotton MAdidas Vintage Football Shirt Soccer Jersey 1970's Rare *made In Usa* Large Vintage 1950s Rayon Gabardine Sport Shirt Van Heusen Small Apricot Shell Buttons