The vintage men's shirt is the cheapest and most versatile piece in a secondhand wardrobe: lumberjack flannel, CPO-style overshirt, oxford button-down, or western snap-button, each family wears and layers differently. The result, often for under €30, is layering with real character and cuts you just don't find new at the same price anymore.
Plaid shirts: where does real lumberjack flannel come from?
The plaid flannel we know today comes from 19th-century American and Canadian sawmills: Woolrich started selling it to logging families as early as 1850, and the red-and-black pattern took the name "buffalo plaid" because the brand's founder owned a herd of bison. A genuine heavy flannel weighs around 8 ounces (roughly 270 g/m²) — noticeably denser than the thin flannels found in fast fashion today, which explains why vintage pieces often hold their shape better over time.
The most reliable clue secondhand isn't the label but the nap of the fabric: a flannel brushed on both sides, dense to the touch, has a good chance of being a genuine workwear piece rather than a lightweight version. Our entire vintage shirt selection goes through this kind of check before being listed.
Overshirt, CPO, chamois shirt: what's the difference from a jacket?
The overshirt is a shirt cut from a jacket-weight fabric (heavy denim, wool, chamois) and designed to be worn over a t-shirt or sweatshirt, not underneath — the CPO is its military ancestor: a heavy wool garment worn by US Navy petty officers starting in the 1930s. The official "Shirt, Wool, Blue" had a straight, boxy cut with one or two flap chest pockets, designed to layer over the uniform — veterans brought it home after the war, and the work garment became a civilian layering piece.
At STO, this workwear category is one of the most requested: we've had, for instance, a Levi's Men's Regular Workwear Shirt, XXL, 6/10, €25.90 — a roomy cut, heavy fabric, exactly the kind of piece to wear open over a henley rather than buttoned to the top. To dig further into the wider workwear category (Carhartt, Dickies, Ben Davis), we detailed the cult pieces in our vintage workwear selection.
Oxford button-down shirt: why has this collar survived a century?
The button-down collar was born from a very concrete problem: in 1896, John Brooks saw English polo players pin their collars down so they wouldn't flap in the wind during play, and Brooks Brothers turned it into a shirt in 1900 — the Original Polo Button-Down Oxford, still produced today. In 2025, the house celebrated the collar's 125th anniversary, proof it never really left the closet.
The detail that sets a genuine oxford button-down apart from a standard dress shirt: the collar doesn't lie completely flat, it keeps a slight "roll," and you'll often find a box pleat in the middle of the back for ease of movement. A piece like the Lacoste Men's Regular 2000s Preppy Shirt, L, 7/10, €41.90 we've had recently illustrates this smart-casual category well — the kind of shirt that goes from the office to Saturday without effort, available in our Lacoste selection.
Western snap-button shirt: workwear born from the cowboy?
The western snap-button shirt comes straight from American ranches of the 1930s, and the pearl snaps we associate with it date back to 1946, invented by Jack Weil, founder of Rockmount Ranch Wear in Denver, taking inspiration from a tailor who put glove snaps on shirts. The appeal wasn't purely stylistic: a snap gives way instantly if the sleeve catches on a saddle horn, unlike a regular button — a genuine safety argument for a work garment.
The western shirt then crossed over into fashion in the 1950s, popularized on screen by figures like James Dean. Secondhand, you mostly come across denim or plaid poplin versions like the Hilfiger Denim Men's Regular Casual Chic Shirt, XXL, 5/10 (visible wear), €15.90 — a piece clearly listed with its flaws, because that's also part of the honesty behind an STO grade out of 10.
How do you wear a vintage shirt in layers?
Three simple ways to wear one: wide open over a t-shirt like a light, relaxed jacket, buttoned all the way up and tucked in for a dressier result, or half-buttoned over a crewneck, double-denim streetwear style. The basic rule: the heavier the fabric (flannel, overshirt), the better it works open and roomy; the lighter it is (oxford), the better it works closed and close to the body.
A piece like the Levi's Men's Regular 1990s Vintage Shirt, XL, 6/10, €46.90, like the ones found in our Levi's selection, lends itself well to both: buttoned with raw denim for a neater look, or wide open over a sweatshirt for something more relaxed. The key is not to treat it like a suit shirt — the fold, the rolled-up sleeves, nothing too stiff.
What size should you take for a vintage shirt or an overshirt?
For an oxford or a classic western shirt, stick to your usual size, trusting the chest measurement rather than the label; for an overshirt or a heavy flannel, size up to have room to layer a t-shirt or a sweatshirt underneath.
Two concrete checkpoints for an overshirt: you should be able to raise your arms above your head without the bottom riding up and exposing your stomach, and the hem should cover the waistband without dropping below the fly. If you're torn between two sizes secondhand, take the bigger one — a piece that's too roomy can be salvaged by wearing it open, a piece that's too small never can.
What should you check before buying a vintage shirt secondhand?
Five points to check systematically: the state of the collar and cuffs (the most rubbed zones), the buttons (missing or mismatched, easy to fix), the buttonholes (not torn), the inside seams (even stitches, no holes), and the smell (a stale odor that doesn't go away with washing is a bad sign).
- Collar and cuffs: look for yellowing, pilling, or fraying — these are the first zones to give out.
- Buttons: mismatched mother-of-pearl, horn, or metal buttons aren't a dealbreaker, just a sign that a button was replaced at some point.
- Buttonholes: check they aren't widened or split, especially the collar one.
- Seams: turn the shirt inside out, the stitches should be even and tight, with no loose threads.
- Smell: smell the fabric up close, at the armpit and under the collar; an odor that lingers despite airing out rarely comes out in the wash.
How do we prep a vintage shirt at STO?
Every shirt that passes through STO is hand-sorted and graded out of 10 based on its real condition (wear, buttons, fading), then machine-washed cold, inside out, and air-dried — never tumble-dried. It's the same method we recommend for at-home care, simply because we apply it ourselves to everything that passes through our hands before joining the shop.
Flannel, overshirt, oxford, western: which vintage shirt to choose for the occasion?
| Type | Origin / signature | How to wear it |
|---|---|---|
| Lumberjack flannel | Buffalo plaid check, heavy brushed cotton (~8oz) | Open over a t-shirt, or closed as a light jacket |
| Overshirt / CPO | Derived from the US Navy petty officers' jacket | Wide open over a sweatshirt, never buttoned to the top |
| Oxford button-down | Pinned collar of polo players, Brooks Brothers 1900 | Closed, tucked in, with straight pants |
| Western snap-button | American ranches, Rockmount pearl snaps 1946 | Open over a tee, sleeves rolled up |
FAQ
Are overshirt and CPO shirt the same thing?
Not exactly: the CPO is a specific historical model (the wool jacket of US Navy petty officers), while "overshirt" is a generic term for any heavy shirt designed to be worn over a t-shirt or sweatshirt, whatever the fabric.
What size vintage shirt should I take if I'm between two sizes?
Take the larger size, especially for an overshirt or a heavy flannel meant for layering: a roomy piece can be salvaged by wearing it open, a piece that's too tight can't.
Is a vintage shirt with missing buttons a problem?
No, that's one of the easiest flaws to fix — a mismatched button can be replaced in a few minutes. It's the state of the collar, the seams, and the buttonholes that deserve closer attention.
How do you get a stale smell out of a vintage shirt?
A cold wash, inside out, followed by air-drying (never a tumble dryer, which locks in odors and damages old fibers) is enough in most cases. If the smell persists after two washes, better to move on to another piece.
Is the oxford shirt only for dressy outfits?
No, that's actually its strength: originally designed as a more comfortable alternative to a suit shirt, it works just as well closed under a sweater as wide open over a plain t-shirt, in a casual version.