The Best Secondhand Men's Shirts to Collect: A Genuine, Practical Guide From Someone Who Handles These Every Week

I look at a lot of secondhand shirts. Every week, without fail, I'm going through piles of them, holding them up to the light, checking collar seams, squinting at labels, deciding what stays and what goes back. After years of doing this, I've developed strong opinions about which shirts are worth collecting, which are worth wearing hard and which aren't worth your time or money at all. This guide is my honest attempt to share all of that in one place, so you can shop smarter whether you're just starting out or already have a wardrobe full of pieces you love.

What does "collectible" actually mean for a secondhand shirt?

It's worth being clear about this upfront, because "secondhand shirts" covers everything from a faded high street flannel to a deadstock 1980s Oxford in pristine condition. A truly collectible shirt has three things going for it: strong original quality, an era or brand that people genuinely want, and enough character that it can't just be replicated by walking into a shop today. That last one matters more than people think. There's no point tracking down a mediocre piece from a mediocre brand just because it's old. Age alone is not the point. Quality and story are.

The good news is that the brands and shirt types I'm about to cover tick all three boxes. These are pieces I actively look for, pieces I know our customers love, and pieces that hold their value or even appreciate over time.

The shirt types worth focusing on

Oxford cloth button downs (the OCBD)

If I could only collect one type of secondhand shirt, it would be the Oxford cloth button down. The OCBD is the backbone of American menswear. The weave is heavier and more textured than a poplin, it softens beautifully with washing, and the button down collar gives it a casual, effortless quality that a dress shirt simply doesn't have. A good vintage OCBD in white, pale blue, pink or classic stripe is a piece you will reach for constantly.

The brands to focus on here are Ralph Lauren (specifically the Polo Ralph Lauren line and the older "Polo by Ralph Lauren" label from the 1980s and early 1990s), Brooks Brothers (whose OCBD collar roll is genuinely legendary among menswear enthusiasts) and, at the more accessible end, Gant. A solid vintage Polo Ralph Lauren Oxford in good condition will typically cost you between €20 and €50 secondhand depending on the era and condition. A Brooks Brothers "Made in USA" OCBD from the same period can go for €30 to €70. Worth every cent.

Piqué polo shirts

Polo shirts are the other obvious category, and they are hugely popular in the secondhand market right now. The key distinction is fabric: you want piqué cotton, not a thin synthetic blend. The piqué weave has a subtle texture, holds its structure, and ages much better than smoother alternatives. Genuine vintage Lacoste and Ralph Lauren polo shirts are made from piqué cotton, and you can feel the difference immediately when you pick one up.

For polo shirts specifically, the 1980s and early 1990s pieces are the sweet spot. The construction was better, the cotton was heavier, and the fits were often slightly more generous in a way that works brilliantly today. Expect to pay €15 to €40 for a good condition vintage Lacoste piqué polo and roughly the same for a Polo Ralph Lauren pony logo polo from the same era. Rarer colourways or deadstock pieces can go higher, sometimes €60 to €80. I've written a full guide on how to style vintage polo shirts if you want ideas on how to wear them once you find them.

Flannel shirts

A good flannel shirt is one of the most satisfying pieces to find secondhand. The best vintage flannels are heavy, brushed, 100% cotton and have that warm weight that modern fast fashion simply cannot replicate. They feel like they mean something. The brands to look for here are Ralph Lauren (their flannel button ups from the 1990s are excellent), Pendleton (American made wool blend flannels that last decades), and Five Brother, which is a less famous but genuinely brilliant American workwear brand known for its Cone Mills cotton flannels.

Vintage flannels typically sell for €15 to €45 secondhand, with deadstock examples or particularly striking plaids commanding more. What I love about them as collectibles is that they are still very accessible price wise, but the quality gap between a good vintage flannel and anything made today is enormous.

Hawaiian and camp collar shirts

These have had a massive moment in recent years and they are not going anywhere. A genuine vintage Hawaiian shirt, what collectors call an "aloha shirt," is a completely different proposition from the cheap printed shirts you see everywhere today. The best ones are made from rayon or cotton, the patterns are printed on the fabric rather than onto a white base cloth, and the seams are often matched at the chest and sides. Sun Surf, Reyn Spooner, and older Kahala pieces are grail territory, but you can find wonderful examples from Ralph Lauren, Tommy Hilfiger and even Levi's at far more reasonable prices.

Price range for collectible camp collar and Hawaiian shirts runs from about €20 for a good Tommy Hilfiger example up to €150 or more for a true vintage Sun Surf or deadstock Japanese aloha shirt. The detail to look for: matched seam patterns, coconut or wood buttons, and a label that confirms rayon or cotton rather than polyester.

Oxford and poplin dress shirts worth collecting

A slightly less obvious category, but one I think is underrated. Classic Italian and British dress shirts from the 1980s and 1990s, brands like Ermenegildo Zegna, Brioni, Turnbull and Asser or Harvie and Hudson, turn up at charity shops and estate sales for a fraction of their original retail prices. A Zegna 100% cotton poplin dress shirt that cost €400 new can be found secondhand for €25 to €60 in excellent condition. The quality of the cloth, the hand stitching on the collar and the mother of pearl buttons give them away immediately. These are pieces you genuinely cannot buy new at that price point. I wrote about how to spot quality in a secondhand dress shirt in detail if this category interests you.

The brands worth collecting, and why

Ralph Lauren

Ralph Lauren is the single most reliable brand to collect in secondhand menswear, and shirts are no exception. The key is knowing which line you're looking at. Polo Ralph Lauren is the main line with the pony logo. The older "Polo by Ralph Lauren" label, typically in navy blue with the name in a box, indicates production from roughly the late 1970s through to the early 1990s and is the most desirable for collectors. Made in USA examples from this period are the real prize.

On authentication: the construction on genuine vintage Ralph Lauren is reassuringly solid. Check that the collar attachment is neat on both sides, that the buttons are real pearl or horn rather than cheap plastic, and that the polo pony embroidery (where present) has clear definition, a proper rider posture and no bleeding threads. The label font should be crisp and evenly spaced. Ralph Lauren is one of the most counterfeited brands in the vintage market, so take your time. I always recommend cross referencing the label with dated examples online before committing to a high price piece.

Lacoste

Lacoste shirts, both polos and the less common woven button downs, are genuinely collectible. The brand's quality standards have remained unusually consistent over the decades, which means a well kept 1980s Lacoste polo is often indistinguishable in quality from a new one, but it has the heavier cotton and slightly boxier cut that many people now prefer. The crocodile logo on genuine pieces is embroidered with clear definition, the buttons have two holes only (not four) and are sewn vertically. The French made pieces from the 1970s and 1980s are particularly well regarded. Expect to pay €15 to €45 for a good secondhand Lacoste polo.

Tommy Hilfiger

1990s Tommy Hilfiger is having an enormous moment right now. The bold flag logo shirts, the spellout button downs, the striped rugby style pieces from the mid 1990s peak era are all highly sought after. The best Tommy shirts from this period are 100% cotton, well constructed, and carry that confident, slightly preppy American energy that feels completely fresh today. Made in USA or Bangladesh Tommy pieces from 1992 to 1999 are the most collectible. Prices run from €20 to €60 depending on style and condition, with particularly bold graphics or hard to find colourways going higher.

Brooks Brothers

For OCBD purists, Brooks Brothers is the ultimate reference. The brand invented the oxford cloth button down shirt and their vintage pieces, particularly the "Made in USA" examples from before the early 2000s, are exceptional. The collar roll on a genuine vintage Brooks Brothers OCBD is distinctive: it doesn't lie flat, it has a natural, slightly rumpled curve that people have been trying to replicate ever since. These shirts can be found for €25 to €60 secondhand and they are virtually impossible to wear out if you treat them well.

Gant and Gitman Brothers

Two brands that are slightly under the radar but consistently excellent. Gant, the Swedish-American brand, made beautiful oxford shirts from the 1970s onwards and their vintage pieces are often overlooked by casual buyers, which means prices stay reasonable: €15 to €35 for a good example. Gitman Brothers (now Gitman Vintage) is a cult favourite among proper menswear enthusiasts for its heavyweight pinpoint oxford shirts and Japanese selvedge pieces. Harder to find secondhand but worth hunting.

How to assess condition: the three things that matter most

Condition is everything with collectible shirts. Here is what I check, in order of importance.

• Collar wear and yellowing. This is the single biggest issue with secondhand shirts. Hold the collar up to the light and look for thinning fabric on the collar points and along the fold line. Light yellowing can often be washed out. Actual fabric thinning or pilling on the collar is permanent and significantly reduces the value and enjoyment of the piece.
• Cuff condition. Cuffs get rubbed, frayed and stained more than any other part of a shirt. Check both cuffs carefully on the underside. Minor fraying is acceptable on a very old flannel worn as a casual piece. On an OCBD or dress shirt, the cuffs should look clean and intact.
• Underarm and body staining. Turn the shirt inside out and check the underarm panels. Yellowing here is very common and can sometimes be treated, but deeply set staining usually cannot. Also check around the lower buttons on the front placket, where food and drink stains tend to gather.

Beyond those three, also check that all buttons are present and original, that there are no moth holes (hold the fabric up to the light and look for tiny pin pricks), and that any embroidery or logo detail is undamaged. A shirt that passes all of those checks in a genuinely desirable brand is a good buy at almost any reasonable price.

How to read the label and date the piece

Learning to read vintage clothing labels is genuinely one of the most valuable skills you can develop as a collector. The label tells you the era, the line, where it was made, and sometimes the original retail tier. For Ralph Lauren, the navy "Polo by Ralph Lauren" label in a box format indicates older production, typically 1970s to early 1990s, while the later "POLO RALPH LAUREN" label in a different format suggests post mid 1990s. For Tommy Hilfiger, the flag logo design changed several times through the 1990s and 2000s, and comparing the label to a dated reference guide online takes about two minutes and saves you from buying a recent reissue at vintage prices.

I've put together a full guide to reading and dating vintage clothing labels if you want to go deeper on this. It covers the key brand timelines and exactly what to look for.

Realistic price guide (in euros)

• Vintage polo shirt (Lacoste or Polo Ralph Lauren, 1980s/90s, good condition): €15 to €45
• Vintage OCBD shirt (Polo RL or Brooks Brothers, good condition): €20 to €60
• 1990s Tommy Hilfiger button down or flag shirt, good condition: €20 to €55
• Vintage flannel shirt (Ralph Lauren, Pendleton, Five Brother): €15 to €45
• Italian dress shirt (Zegna, Brioni, excellent condition): €25 to €80
• Vintage Hawaiian or camp collar shirt (Sun Surf, Reyn Spooner): €40 to €150
• Deadstock or unworn example of any of the above: add 30 to 100% to the above ranges

These are real, current secondhand market prices. You will occasionally find bargains below these ranges and you will occasionally see sellers asking much more, particularly on platforms like Depop or Grailed where hype inflates prices. Know the reference range and don't panic buy.

Caring for the shirts you collect

A good secondhand shirt can last another thirty years if you look after it properly. Wash OCBDs and flannels at 30 degrees, inside out, on a gentle cycle. Never tumble dry a cotton Oxford if you want to keep the fabric structure intact. Hang to dry on a proper hanger and pull the collar and cuffs into shape while still damp. For piqué polos, the same applies: cool wash, hang dry, and avoid high heat which collapses the weave over time.

For storage, hang shirts on wooden or padded hangers rather than wire ones, which distort the shoulders. If you're storing them for a season, avoid plastic garment bags, which trap moisture. A breathable cotton cover is much better. And if a shirt comes to you with a musty or vintage smell, a cold soak with a small amount of white vinegar followed by a normal wash at 30 degrees usually sorts it out completely.

Where to find the best secondhand shirts

The honest answer is: everywhere and nowhere in particular. The best finds often come from estate sales, charity shops in affluent areas, and specialist curated vintage shops like ours, where the work of sorting and authenticating has already been done for you. Online, eBay is still the largest single market for vintage shirts and has genuinely great pieces if you search carefully and check seller history. Depop and Vinted have good volume at the accessible price end. Grailed skews more expensive but has serious pieces.

The thing I'd caution against is just searching for a brand name and buying the first thing that looks right. Take your time with photos. Ask for measurements. Ask for a picture of the label. A good seller will always be happy to provide these. If they aren't, that tells you something.

If you are ready to start building your collection or add a few carefully chosen pieces to what you already have, take a browse through the Revaleur shop. Everything we carry is personally selected and checked before it goes online. No fillers, no uncertainty, just genuinely good shirts worth owning.