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 40s Mark Twain Rayon Loop Collar Hawaiian Shirt Med Fish Atomic Aloha 50sVintage Early Indian Motorcycle Sweater Jersey Shirt Old Sweatshirt Clothing VtgVintage 80s Motorhead No Remorse Born To Lose Live To Win Shirt Size Medium RareZorlac Pushead Pirate Skull Rare Original Vintage Shirt Large Ex Cond !!!!Rare Vintage 1960's Levis Winchester Western Shirt S/m- Original - Mint CrispVintage 3d Emblem Easyriders J.e. Morgan Made In Usa Long John Shirt Sz SVintage 1988 1989 Guns N Roses Appetite For Destruction La Coliseum Shirt Size LVintage Ozzy Osbourne 1986 Ultimate Sin Jersey Raglan Tour Shirt Size LargeLot Of 47 Vintage Western Shirts Pearl Snaps Rockabilly 70s 80s 90s LargeVintage 1930's/40's Barn Find Penny's Sanfornized Chambray Work Prison Shirt Sepultura Schizophrenia Original Vtg 1997 Longsleeved Shirt Blue Grape Not PatchVintage Wasp 1986 Blind In Texas Tour Shirt Size Large Rare!!!Vtg 40s 50s Miller Green Gabardine Wool Western Shirt Rare Pearl Snap RockabillyVintage Nike Challenge Tennis Shirt Agassi Court Polo 90s Size LThe Beatles ! Rare Apple Corps / Ben Sherman Beatles Design Shirt. 46" ChestNos! Vintage 40s Weldon 3-pc Rayon Polka Dot Pajamas Pjs Shirt Top Pants Robe MVintage 1981 Rolling Stones Us Tour Shirt Knits Size LargeVtg Sears Nos Flannel Plaid Shirt Medium Deadstock Blue Multi Usa Reg WeightVintage The Who 1989 The Kids Are Alright Tour Shirt Size XlVintage Levis Chambray Work Shirt Long Sleeve 70s Usa Large Euc Sports EmbroiderVintage 1981 Rolling Stones Jersey Tour Shirt Knits Size SmallVintage Guns N Roses 1993 Spaghetti Incident All Over Print Shirt Size LargeVtg Lee Westerner Shirt Denim Sanforized 40s LookVintage 90s Tommy Hilfiger Sailing Gear Shirt, Xl, Hip Hop, Polo, RareVtg Workwear Shirt Chain Stitched Sanforized Work Mechanic Shop Jacket MediumBig Yank Reliance Vintage Chore Work Shirt JacketVintage 1950s Cotton Hookano Hawaiian Aloha Shirt With Fishing Design Med 46" Vtg Mens Pendleton Wool Flannel Blue Gray Loop Collar Usa Shirt Plaid LargeVintage Lot Of 13 Harley Davidson / Biker T-shirts Medium , 1xl,1 SVintage Short Sleeve Dunbrooke Bowler 50's Era Bowling Shirt Mens 25" Pit To PitVtg 1970s Polo Ralph Lauren Wool Hunting Shirt Mens L Rare Leather ShoulderVintage Lot 16 Harley Davidson & Biker T-shirts LargeVtg Sears Nos Flannel Plaid Shirt Medium Deadstock Blue Multi Usa HeavyweightVintage Embroidered California Ranchwear H Bar C Pearl Snap Western Shirt MediumVintage 1950s Red Silk Hawaiian Aloha Shirt King Kamehameha Statue L/xlMen's Casual 1950's Waist ShirtUltra Rare Nine Inch Nails Shirt Pretty Hate Machine Thrashed Vintage Xl ReznorPaul Smith Great Shirt Very Rare Awesome Sz 18 Xxl Cotton Logo Vgc Made Italy2 Antique Men's Ls Shirts 15 Neck Faded Blue Stripe / Off White2 Antique Men's Ls Shirts 15 Neck Off White/ Placket & Faded StripeVtg 70s Ely Plains Western Plaid Shirt Pearl Snaps Embroidered L/xl VgcVintage 70's Maverick Denim Western Snap Shirt 15.5 Dark Indigo Wrangler Levi'sVintage Alice Cooper 1986 The Nightmare Returns Tour Shirt Paper Thin Size LargeNos Vtg Yarmo Smock Work Chore 40 Lk Ww2 Lk Overhead Cotton ShirtVintage 70s Mens Burgundy Gold Geometric Retro Disco Shirt Big Lapel MediumVintage 50's "california Ranch Wear Los Angeles" Western Shirt Dan River FabricVintage 50s Ivy Hall Mens Button Down Collar Dress Shirt Ss Sz M Back LoopVintage 50s Scully Rawhide Leather Western Fringe Shirt Jacket Top S/mVintage 1987 Def Leppard Hysteria Tour Shirt Size MediumVintage 80s Elvis Costello Shirt Size LargeVintage Big Mac Penneys Chambray Denim Shirt Size M Embroidered Western HippieVintage 50s Moss Mens Traditional Button Down Ss Shirt Sz. M Black White StripeMen's Casual 1950's Waist ShirtVintage 60s Mens 'mr California' Shirt Royal Blue Short Sleeved Size LargeVtg 60's Mens Nehru Dress Shirt Jacket Cream Wool Fancy Ribbon Trim Sz L Hippie Mens 50s Vintage Dan River Dan Plaid Button Up Cotton Casual Shirt Sz LVtg 50s Mens Arrow Cum Laude Sanforized Stripe Button Down Pullover Shirt 15.5Vintage Polo Ralph Lauren Color Block #3 Narco Polo Shirt Mens MMen's Casual 1950's Waist ShirtVintage 1990s Mens Hawaiian Novelty Michigan Hockey Team Shirt Sz Xl