Men's Secondhand Shirt Fit: How It Should Look (And What to Do When It Doesn't)

Every week I go through a pile of shirts at Revaleur. Ralph Lauren Oxford cloths, Lacoste piqué polos, Tommy Hilfiger chambray button-downs, the occasional Gant or Fred Perry. I pick each one up, hold it against the light, check the seams, then try to imagine how it will sit on a real person's body. Fit is genuinely the thing I think about most. You can have a beautiful piece of cotton, a great colour, a brand name worth something, and if it sits wrong on your shoulders it looks like you borrowed it from someone else.

This guide is for men buying secondhand or vintage shirts, whether from a shop like Revaleur, from Vinted, from a car boot or from a charity shop. The fit rules are largely the same as for new shirts, but there are specific things about secondhand and vintage pieces that change the picture entirely. Sizing drift over decades, shrinkage from years of washing, the unreliability of the tag, what a tailor can and cannot fix. That is what the other guides on this topic miss. So let us go through it properly.

Why fit matters more with secondhand shirts than with new ones

When you buy a new shirt, you know what you are getting. The tag says M, the brand's size chart tells you the chest measurement, and the garment has not been washed fifty times. With a secondhand shirt, you are dealing with a piece of clothing that has a history. It may have been washed in hot water. It may have been tumble dried repeatedly. The original owner may have been a different shape to you entirely. The tag is a starting point at best and a red herring at worst.

This is why fit matters more here, not less. A €180 Ralph Lauren shirt bought secondhand for €35 is a brilliant deal if it fits. It is a waste of €35 if it does not. And unlike buying new, you cannot return most secondhand pieces or easily exchange for the next size up. Getting your eye in on fit before you buy, whether in person or from a listing with measurements, is the skill that separates good secondhand dressing from a wardrobe full of things you never wear.

The one rule that overrides everything: ignore the tag size

I want to say this clearly before anything else. The size on the tag of a vintage or secondhand shirt often means very little. There are two reasons for this.

The first is historical sizing drift. Clothing brands have been gradually cutting their garments bigger for the same tagged size for decades. A shirt tagged Large from 1985 was likely cut for a 40 to 42 inch chest. A shirt tagged Large from a major brand today is often cut for a 44 to 46 inch chest. So a vintage Large can easily fit like a modern Medium or even a slim Medium. This is not a fault in the shirt. It is just how the industry changed.

The second reason is shrinkage. Cotton and other natural fibres shrink over years of washing, especially if washed hot. The chest and body of the shirt can shrink by a full size or more, while the collar and shoulder yoke, which are reinforced and structured, tend to hold their shape better. This creates a shirt that may feel fine across the shoulders but tight everywhere else. Or the opposite: a shirt that sat very boxy on the original owner and has since shrunk into something closer to a fitted cut.

The only number that matters is the actual measurement of the garment. When buying online, always ask for the pit-to-pit chest measurement (armhole seam to armhole seam across the chest, laid flat) and the shoulder width (seam to seam across the back). Double the pit-to-pit figure to get the full chest circumference. Compare that to a shirt you already own and wear comfortably. That is your guide. Not the tag.

The shoulder seam: the single most important check

If you learn one thing from this article, make it this. The shoulder seam is where the sleeve is attached to the body of the shirt. It should sit right at the edge of your shoulder, at the point where your shoulder rounds into your arm. That bony point is called the acromion and it is your reference.

If the seam drops down onto your upper arm, the shirt is too large. It will look shapeless and the sleeves will hang off you. If the seam pulls in toward your neck, the shirt is too small and you will feel restricted every time you lift your arms.

Why is this the most important check? Because the shoulder is the one part of a shirt that a tailor cannot easily correct. Taking in the side seams, shortening the hem, adjusting the cuff, even taking in the back of the collar; these are all straightforward, affordable alterations. Resetting a shoulder seam is a major reconstruction. It costs a lot, takes significant skill and often changes the look of the shirt entirely. So if the shoulders do not fit, move on.

One nuance for the vintage or oversized look: if you are deliberately going for a dropped shoulder, relaxed silhouette (think an 80s or 90s Ralph Lauren Oxford worn loose), then a seam that sits slightly onto the upper arm can be intentional and good-looking. But even then, it should not fall more than about 2 centimetres past the shoulder point. Beyond that it just looks like you are wearing your dad's shirt.

Chest and torso: room to move without billowing

After the shoulders, the chest is the next thing to assess. Stand up straight and button the shirt fully. The placket (the central button strip) should lie flat. If it pulls open and you can see X-shaped tension lines across the chest, the shirt is too small. You should be able to take a full breath and move your arms forward without the shirt straining.

On the other side, a shirt that billows out around your torso and creates a parachute effect looks just as bad as one that is too tight. Pinch the fabric at the side of your body with two fingers. You want to be able to gather roughly 3 to 5 centimetres of fabric. Less than that and it is too tight. More than about 8 centimetres and it is quite loose.

The good news here is that a too-loose torso is fixable. A tailor can take in the side seams of a shirt for somewhere between €15 and €30, depending on where you go and how much fabric needs to come out. It is one of the cheapest and most transformative alterations in menswear. A shirt that fits perfectly in the shoulders but hangs loosely in the body can be made to look sharp for very little money.

Note that vintage shirts, especially those from the 1980s and 1990s, were often cut with a straighter, boxier silhouette through the body. This was not a mistake in the cut. It was the style. Brands like Ralph Lauren, Tommy Hilfiger and Lacoste all made shirts with a more relaxed, straight-sided fit in that era. Whether you want to keep that silhouette or have it taken in slightly is a style choice, not a fit emergency.

How each type of shirt should fit: a quick breakdown

Oxford button-down shirts (OCBD)

The Oxford cloth button-down is probably the most common shirt I sell at Revaleur. Ralph Lauren makes the definitive version. It should fit with a little ease through the body, not skin-tight. The collar points should button down flat. Sleeves should reach the base of your wrist. The shirt should be long enough to tuck in without coming untucked when you bend over, but not so long that it hangs below the mid-thigh if you wear it out. A well-fitting OCBD that you have had taken in slightly at the sides is one of the best-looking things a man can wear. Budget €35 to €80 for a good secondhand Ralph Lauren or Gant Oxford, and perhaps €20 for a tailor to nip it in if needed.

Polo shirts

Polo shirts are less forgiving of poor fit because the knit fabric shows every bump and pulls visibly when too tight. The shoulder seam should sit at the edge of the shoulder, the same rule as for woven shirts. The collar should frame the neck without gaping or choking. The sleeves on a polo should end around mid-bicep. The hem should sit about 5 centimetres below your waistband when worn untucked. Lacoste and Ralph Lauren polo shirts second-hand typically run between €25 and €65 depending on age and condition. Vintage Lacoste from the 1980s tends to run one to two sizes smaller than modern Lacoste due to both the era's sizing standards and decades of washing.

Casual button-down shirts (chambray, flannel, poplin)

These can be worn slightly more relaxed than a formal Oxford. The shoulders still need to sit correctly. The chest should allow free movement. For an untucked casual shirt, the hem should end somewhere between the middle and bottom of your trouser fly, not past your trouser pockets. If it hangs lower than that, it looks sloppy. If it ends above the fly, it will ride up and look too short. Tommy Hilfiger and Gant make a lot of these in slightly different cuts. Tommy often cuts a little wider in the body, Gant tends to be slimmer through the chest in their more recent pieces.

Dress shirts

The fit rules are the same for the shoulders, chest and sleeves. The key additional check is the collar. You should be able to fit two fingers between your neck and the closed collar. Any tighter and it is uncomfortable. Any looser and it looks like you have lost weight since you bought it. The shirt should be long enough to stay tucked in comfortably throughout a full day of movement. Dress shirts from good brands like Profuomo or Suitsupply bought secondhand can offer extraordinary value. A Profuomo shirt that retailed at €120 can be found secondhand for €25 to €45 in excellent condition.

Sleeves: length and fit at the bicep

For a long-sleeved shirt, the cuff should sit at the base of your wrist, right where your wrist meets your hand. That is the standard. In practice, with vintage shirts, sleeve length is one of the things that shrinkage affects most noticeably. A shirt that has been washed hot many times can have sleeves that are half an inch or more shorter than intended. Check that the cuffs reach the wrist bone when you hold your arms relaxed at your sides.

Sleeve width at the bicep matters too, especially for men who work out or have naturally larger arms. The fabric should wrap the arm without gripping it. You should be able to raise your arm fully without the sleeve pulling against your bicep. If you feel resistance across the upper arm when you reach forward, the shirt is too narrow in the sleeve and there is little you can do about it without major reconstruction.

For short-sleeved shirts and polos, the sleeve should end around the mid-bicep. Sleeves that end near the shoulder make the shirt look too small. Sleeves that reach toward the elbow can look oversized unless that is the specific look you want. Again, vintage polo shirts from the 1980s often had slightly shorter sleeve proportions, which can look excellent when worn deliberately.

The collar: the frame for your face

A collar that does not fit correctly makes an otherwise good shirt look wrong instantly. For a dress shirt or Oxford, the test is the two-finger rule: close the top button and slide two fingers inside the collar. Comfortable and snug is right. Tight is wrong, and there is very little a tailor can do about a collar that is too small. A collar that is slightly too loose can be taken in, but it is fiddly work. Get the collar right when you buy.

For polo shirts, the collar is a knit and softer. It should lie flat against the neck without gaps. A collar that curls up, folds or stands away from the neck has either been overwashed, stretched, or ironed incorrectly. On vintage Lacoste and Ralph Lauren polos, look at the collar carefully. A flat, structured collar in good condition is a sign the shirt has been well cared for. A curled or deformed collar can sometimes be pressed flat again with careful ironing, but if the knit has permanently stretched it is very hard to restore.

What a tailor can fix, and what they cannot

This is the part of the guide that most fit articles skip entirely, and it is genuinely useful to know before you buy.

• Can be fixed cheaply (€10 to €30): Side seams taken in to slim the body. Hem shortened. Sleeve length shortened. Cuff taken in slightly. Collar taken in slightly if it is a woven shirt.
• Can be fixed but costs more (€30 to €60): Sleeve width reduced. Back darts added. Significant body reshaping.
• Very difficult or not worth doing: Resetting shoulder seams. Widening a collar that is too small. Lengthening a sleeve that has been cut or shrunk too short. Adding fabric to a shirt that is too small anywhere.

The practical rule: buy for the shoulders and the collar, fix everything else with a tailor. If both of those are right, the rest of the shirt can almost always be made to work.

Brand sizing quirks you should know

Buying secondhand designer means you encounter the same brands repeatedly. Here is what I have learned from handling hundreds of pieces at Revaleur.

Ralph Lauren Polo: Current Ralph Lauren tends to run true to size in the chest but can be quite generous in the body. Vintage Ralph Lauren from the late 1980s and 1990s runs noticeably smaller, especially in the chest and sleeve. A tagged XL from 1992 often fits like a modern L or even a slim L. If you are buying vintage Ralph Lauren, always get measurements rather than trusting the tag. We have a full guide to Ralph Lauren Polo sizing for men if you want to go deeper on this.

Lacoste: Vintage Lacoste polos, especially anything from before 2000, runs small. The brand originally used French sizing which adds another layer of confusion. A French size 5 is roughly a modern M/L depending on the era, but shrinkage means most vintage Lacoste in a size 5 fits more like a modern S or S/M. Always measure. Modern Lacoste is more consistent and tends toward a classic, slightly relaxed fit.

Tommy Hilfiger: Tommy from the 1990s was cut quite generously, particularly in the torso, as part of the brand's preppy, relaxed aesthetic. A tagged L from the mid-1990s can fit like a modern XL in the body, even if the shoulders are a normal modern-L width. Great for the oversized look. Less ideal if you want something fitted.

Gant: Generally quite consistent and true to modern sizing. Their Oxford shirts tend to be slightly longer in the body and sleeve than average, which works well for taller men.

The oversized vintage look: intentional versus accidental

Let's be honest about something. Not every shirt needs to fit in the traditional "perfectly tailored" sense. The deliberate oversized vintage shirt look is genuinely good when done right. Broad drop shoulders, extra room in the chest, a shirt that billows slightly. It is a whole aesthetic and it works.

But there is a difference between intentional oversized and "this shirt is just too big for me." The line is the shoulders. If the shoulder seam drops only slightly off your natural shoulder (say, 2 to 3 centimetres), the shirt reads as deliberately oversized. If the seam is hanging halfway down your upper arm, it reads as ill-fitting regardless of what the rest of the shirt is doing. The shoulder keeps the garment anchored. Everything else can be relaxed, but the shoulder needs to be roughly in the right postcode.

If you enjoy the oversized look and want to style it properly, we have a detailed guide on how to style oversized vintage shirts that covers the outfits that make the look work.

How to check fit when buying secondhand online

This is the practical checklist. When you are looking at a listing and trying to decide if the shirt will fit you, here is what to do.

1. Get the pit-to-pit measurement. This is the chest width laid flat. Double it for the full chest. Compare it to a shirt you own and love the fit of.
2. Get the shoulder width. Seam to seam across the back, laid flat. Your shoulder width in a shirt you wear well is your guide number.
3. Get the sleeve length. From the shoulder seam to the end of the cuff. Check this against your arm length.
4. Get the shirt length. From the top of the shoulder seam to the hem. Know whether you are tucking or wearing untucked and work out if the length works for you.
5. Ask about the collar size if it is a dress shirt or Oxford. This is usually on the tag and is more reliable than the general size label, because collar sizing is based on actual neck circumference in inches or centimetres.
6. Look at the photos carefully. Are there tension lines across the chest in the seller's photos? Does the collar look deformed? Are the sleeves bunching at the cuff in a way that suggests shrinkage? A good seller photographs these things flat and in detail. If the photos are bad, ask for more.

At Revaleur, we measure every piece before listing it and include those measurements in the product description. It is not standard practice everywhere, but it should be. If a seller cannot or will not give you measurements, that is a genuine reason to hesitate.

Good fit is not about following rules for their own sake. It is about wearing clothes with confidence and wearing them often. A well-fitting secondhand shirt from a brand like Ralph Lauren, Lacoste or Tommy Hilfiger that you reach for constantly is infinitely more valuable than a pristine unworn piece that sits folded on a shelf because something about it was always slightly off.

If you want to browse shirts that have been measured, assessed and described honestly, have a look at what we have in the Revaleur collection. Every piece goes through exactly the process described in this guide before it is listed.