The first time I ever understood the appeal of vintage clothing was when I was 19 and stumbled across a 1960s Pendleton wool shirt at a Salvation Army in Chicago. The fabric was twice as thick as Pendleton still uses today, the mother of pearl buttons had developed perfect patina, and it was in better condition than most of the new shirts in my closet, despite being at least 40 years old. My grandfather saw me staring at it in the mirror and nodded knowingly. “Things were built differently back then.” Duh, grandpa.
Thanks for stating the obvious. But that lesson has served me well over the last 20 years of thrifting. There’s something deeply ironic about the modern menswear industry.
We live in a world where we’re constantly bombarded by thousands of dollars “heritage inspired” garments that weakly attempt to replicate the quality and feel of vintage clothing (usually with abysmal results), while their real vintage inspirations sit on thrift store racks across America for a fraction of the price. As an admitted thrift junkie who’s spent more Saturday afternoons than he’d care to admit rifling through Goodwill bins and church basement sale tables (my girlfriend got me kicked off of Kick Starter because I paid for a “one afternoon per weekend” limit on my thrifting), I’ve picked up on enough repeat patterns to predict which vintage items consistently outclass their modern equivalents.
This doesn’t include super-obvious vintage collectibles like vintage Levi’s 501s from the ‘50s or deadstock Ivy League-style suits from the ‘60s that have been hunted to oblivion by vintage dealers for decades.
I’m talking about the stuff that nobody pays attention to; high-quality thrift items that most people overlook because they don’t have the right vintage brand name they recognise or don’t fit with current trends. These are pieces that, through years of rifling through racks across America, I’ve come to find have the best quality- to- price ratios and provide unique character that cannot be authentically reproduced. We’ll start with something obvious so I can get it out of the way: military surplus.
Sure, vintage stores will happily overcharge you $300 for an immaculate vintage M-65 field jacket or N-1 deck jacket, but more run-of-the-mill vintage military items turn up in thrift stores all the time. I’ve picked up dozens of USA-made military-issue khaki chinos from the 1980s and 1990s for under $10 that are built to last literal decades. The fabric is thicker and heavier than most modern trousers without being uncomfortable, all of the stitching looks like it could survive nuclear war, and they fade into a beautiful patina that looks nothing like the butchered retro jean stitching you’ll find on mass-produced apparel today.
Speaking of apparel built to survive nuclear war, my favourite thrift finds of all time are military jumpers. Vintage Navy or Army wool jumpers from the 1970s through 1990s will often sell for $5-15 but are built to modern manufacturing standards well north of $200. I picked up an olive drab wool crewneck in Michigan for $6 that would probably sell for $385 as an Aimé Leon Dore “original” today.
These bad boys often have tags from companies like Laurel, Sturdi- Knit, and Vermont Tubbs that shouldn’t be sold without a Confederate officer’s uniform. Look for a 4- or 5-digit military contract number printed on the inside as well. Outside of military apparel, one of my most consistent picks are vintage American- made wool shirts/shirt jackets and cotton work shirts from the 1960s through 1980s.
Companies like Woolrich, Pendleton, and LL Bean made some INCREDIBLY durable wool shirts and shirt jackets during this era that used fabrics several times too thick and heavy to be sold by anyone new today. Not only are they made with heavier fabrics and more plies of yarn, but they were all made in America (while most modern versions are sewn in China or Bangladesh). You can still find these shirts in thrift stores all over the place for $10-20.
One major benefit of vintage wool shirts, beyond heavyweight fabrics, is the construction. Look for chain-stitched hems, bar-tacked stress points, and double-needle stitching that has proven itself capable of surviving 40+ years of wear. You don’t see that kind of craftsmanship and handwork in modern shirts that charge $300+.
They’ll also usually fit much more generously than modern slim-fit shirts, but a $25 adjustment to the side seams at your local tailor can fix that problem. Either way, you’ll end up with a higher quality shirt for less money than buying a “heritage” brand new version. Vintage leather jackets are tough to find unless you know where to look, but they’re absolutely worth it if you do.
I won’t sugarcoat it: if you find a vintage Schott leather jacket in good condition, you’re better off saving up the money to buy a new one because even used Schott will run you over $200. That being said, there are a host of vastly underrated vintage leather makers that haven’t survived to the present day. Cooper Leather, Berman, Foxrun, and Golden Bear all made excellent leather jackets that now sell for a small fraction of their quality level.
I scored a 1970s Golden Bear varsity jacket with a wool melton body and horsehide sleeves in great condition for $35 at a church basement sale in Queens. That jacket would cost upwards of $700 to manufacture today. The trick with vintage leather is spotting what real vintage horsehide and goatskin looks like.
Vintage cowhide was substantially thicker and heavier than modern leather jackets use today outside of luxury prices. If the jacket has cracked or dried out a little, basic leather conditioning with something like Saphir Renovateur can restore leather back to its original glory. I also trust zippers as a tell; vintage leather jackets will often have Talon zippers or early YKK production with the signature oval pull tab.
If there’s one modern menswear category that completely skips over fantastic vintage styles, it’s dress shirts. America was making some beautifully crafted dress shirts from the 1960s through the early ‘90s that are almost impossible to find new today. I’ve found fantastic Oxford cloth and broadcloth vintage shirts from brands like Sero, Troy Guild, Gant, and Eagle in perfect condition for $3-4.
Mid-century oxford cloth was substantially heavier than modern versions, and almost all vintage shirts from this era feature cloth construction details like single-needle stitching (18-22 stitches per inch! ), gussetted construction, and unfused collar and cuffs. There’s a reason these shirts won’t be reproduced; they’re technically superior to anything under $150 that’s being sold today. The one catch to vintage dress shirts is size – they used to size everything differently, and virtually every shirt prior to the mid-80s was expected to shrink to fit once purchased by the wearer.
I typically look for sizes 1-2 shirts bigger than I would normally wear today, particularly if the shirt still looks like it’s deadstock and hasn’t been washed yet. Vintage collars will also usually be longer and fuller than modern slim-collar dress shirts, but A) that style looks infinitely better than the oh-so-fitted necklines we wore in the 2010s and B) actual vintage shirt collar fits are easy to have tailored down. Get with the times, Franz.
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If you’re into knitwear, good news – the vintage industry has you covered. Vintage cotton and wool jumpers from the ’70s through ’90s are incredible, particularly ones made in America. And unlike the obscure brands I’ll get to later, some of the best vintage jumpers you’ll find came from brands everyone knows.
LL Bean’s Norwegian birdseye jumpers from the ’80s aren’t joking when they say they’ll last you a lifetime. While Bean still makes an excellent jumper today, their basic cotton cable knit from decades ago used significantly heavier yarn and denser knitting than what they use now. Classic brands like Brooks Brothers are also made incredible cotton jumpers prior to their manufacturing exodus.
Brooks Brothers cotton from the late ’80s/early ’90s has a distinctly thick and dense hand-feel that comes from using thicker yarns and knitting the yarn more closely together. Mass-producing something like this with modern labour rates is cost-prohibitive, which is why you can often find these in thrift stores for $5-10 while new buyers disregard them for trendier brands. Alright y’all, time for the sleeper-hit secret of fantastic vintage thrifting: American-made camp mocs and boat shoes from the 1980s and early ‘90s.
Early Timberland boots and Sebago shoe used THICK leather compared to their current offerings, and they were both actually built to be resoled decades later (not lasts a few seasons like most shoes today). I’ve picked up made-in-Maine Sebago and Dexter boat shoes for under $15 more than once that just needed a basic cleaning and conditioning to look and feel better than you’ll ever find in retail today (at 5x the price). Hell, even basic vintage leather belts from America are thicker and of higher quality than what you can find at most stores today.
Belts from the ’70s through ‘90s were routinely made from full-grain leather with a thickness you just don’t see anymore except from $250 belt companies. Thrift-store staple brands like Coach, Dooney & Bourke, and even old department store brands (Taylor’s, Marshal Fields, etc.) made simple bridle leather belts that have held up beautifully for decades. These can usually be found for $3-5 and just need a wipe-down with a leather conditioner to remove surface dirt.
And for you weirdos out there who love golf clothes as much as I do: vintage golf clothes are where it’s at. Vintage Sansabelt trousers from the ’70s and ’80s were crafted to a standard that genuinely impresses me even after decades of thrift hunting. The waistbands DO NOT stretch out, like most trousers sold today.
The fabric has a thick, substantial feel that you just can’t find due to modern cotton standards, and the construction details are downright impeccable. Hell, some of the crazier plaids will obviously never work, but you can find solid navy, grey, and tan versions that are deadstock and barely worn with original tags still attached. I have no idea who originally bought these because they refuse to leave the rotation in my closet.
This one may be anecdotal, but the holy grail of thrift items might be vintage American-made pyjamas and robes. Companies like Pleetway and Botany 500 used absurdly high-quality cotton that has lasted me decades, real shell buttons, and piping that was ACTUALLY sewn on. To this day, I have no idea how they kept these things together at such a low price point.
A good vintage cotton robe will last you another 30 years if you take care of it; don’t expect your new $80 Japanese-cotton monstrosity to last half that without falling apart. For whatever reason, thrift shopping feels like a different world than it was 10 years ago. Vintage dealers and online resellers scour thrift stores for profit like pigs in shit, so major metropolitan areas have been picked clean of certain categories.
Vintage denim is picked over. Vintage gymwear is hunted down by collectors. But you’d be surprised at how many high-quality vintage items are still found hiding in thrift store racks across America, especially outside of big cities.
Hat tip to all of the small-town and suburban thrift stores where vintage wool baseball jackets and Polo shirts fly under the radar while racks of Oak Street Bootmakers and XXX-Large Archive get tossed on the sales floor. The best stuff I’ve found in recent years have been from small town thrift stores during work trips. It’s no secret vintage dealers can’t make a profit visiting your average small-town Midwest thrift store, so these are the ones I hunt when I have a few hours to kill.
Stitch-Twill Woolrich mackinaw coats from the ‘60s for $12 in rural Michigan. Brand-new deadstock Viyella flannel shirt for $7 in an obscure Vermont church sale. Brand-new 1980s Coach briefcase for $25 in a suburban Virginia Goodwill.
Keep browsing through those bins, because you never know what you might find.
The rush of finding that perfect vintage item at thrift prices is almost indescribable. To pull something out of a donation bin that cannot be found new at ANY price because the entire fabrication/labour model no longer exists to produce it is almost sickeningly satisfying.
For me at least, there’s something delightfully subversive about wearing a $4 thrifted shirt that is objectively better made than anything you’ll find at Barneys. Of course, vintage comes with plenty of trade-offs. Namely, you have to actually spend time thrifting instead of buying new jumpers shipped straight from overseas factories.
It takes time and patience to find good stuff, and you will go to multiple thrift stores per week without scoring anything you like. Sizes can be tricky if you’re especially tall or broad, and American men were built much differently than they are today. Even when you DO score, your vintage winners typically need washing/drying before wear, and may need minor repairs or tailoring.
But if you’re willing to put in the work, America’s secondhand shops are absolutely littered with decades-old garments that offer vastly superior construction and wear than you’ll find anywhere else for the price. Next time someone compliments my “new” Pendleton shirt, I’ll just grin and omit the part where it’s been keeping strangers warm since John F. Kennedy’s inauguration, and will probably outlast today’s “premium” offerings by another 50 years.
