What Nobody Tells You About Buying Vintage Clothing Online

We wrote a post a while back about how resellers lie to you. That piece was about the seller's side — the misrepresentations, the hype, the games.

This one is for the buyer's side. Because even when a seller is completely honest, buying vintage clothing online is a different experience than walking into a store and trying something on. There are things you need to know that no one tells you. And the learning curve costs money if you figure it out the hard way.

We've been on both sides of this — as sellers who ship hundreds of vintage pieces, and as buyers who source inventory from every corner of the resale market. Here's what we wish someone had told us when we started.

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The Tag Size Means Almost Nothing

This is the single biggest source of returns, disappointments, and wasted money in online vintage shopping. And it's the simplest thing to fix once you understand it.

The size printed on the tag of a vintage garment does not correspond to modern sizing.

This works differently for men's and women's clothing, but the core issue is the same: sizing standards have shifted over the decades. In women's clothing, vanity sizing has been dramatic — a 1950s size 12 is roughly equivalent to a modern 6 or 8. But even in menswear, where sizes are theoretically based on actual measurements (a "Large" should mean the same thing everywhere, right?), the reality is messier than you'd expect.

Here's why vintage menswear sizing trips people up:

Brands measured differently. A "Large" from Carhartt in 1995 and a "Large" from Ralph Lauren in 1995 are not the same garment. Carhartt was sizing for workers who layered flannels and hoodies underneath. Ralph Lauren was sizing for a guy wearing a t-shirt under a polo. The chest measurements on those two "Large" shirts could be three or four inches apart.

Fits changed by era. Menswear in the '80s and '90s was generally cut fuller than the same brands in the 2010s. A "Medium" Carhartt from 1993 might have the same chest measurement as a modern "Large." If you wear a modern medium and order a vintage medium based on the tag, you could end up swimming in it. Or the opposite: vintage workwear from the '70s sometimes ran trim in the body but long in the arms, built for lean guys doing physical labor.

Shrinkage already happened. Vintage denim — especially pre-shrunk vs. rigid — is a minefield. A pair of Levi's 501s marked 34x32 might actually measure 33x31 after decades of washing. Or, if they're rigid/unwashed, they might still be at the pre-shrink size and will shrink 2–4% on their first wash. The tag number isn't the actual number anymore. Sometimes it never was.

International sizing is different. If you're buying a Carhartt WIP piece (the European streetwear line) or anything from a European or Japanese brand, the sizing system is completely different from American workwear sizing. A Japanese XL is often a US Medium. A European 52 is roughly a US 42 chest. Don't assume.

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How to Read Measurements (and What Sellers Get Wrong)

Okay, so you know to check measurements. But do you know what the measurements actually mean? Because sellers aren't always measuring the same way, and a half-inch difference in how the tape is placed can mean the difference between a perfect fit and a return.

Chest / Pit to Pit: This is the most important measurement for any top. It's taken with the garment laid flat, measuring straight across from armpit seam to armpit seam. You then double that number to get the full chest circumference. If a listing says "chest: 23 inches," that means 46 inches all the way around. Compare this to your own chest measurement — you'll want 2–4 inches of ease for a comfortable fit, more if you layer underneath (which you probably do with workwear).

Body length: Measured from the highest point of the shoulder (or back of the collar) straight down to the bottom hem. Sellers sometimes measure from different starting points, so check whether they specify. A jacket that's 28 inches long hits very differently on someone who's 5'8" vs. 6'2".

Sleeve length: In vintage listings, this is usually measured from the shoulder seam to the end of the cuff. But some sellers measure from the center back of the collar down the shoulder and along the arm — which gives a much longer number. Always check which method the seller used. If it just says "sleeve: 34 inches" with no clarification, ask.

Waist (on pants): Measured flat across the waistband, doubled. Here's the catch: a pair of jeans that's tagged "34 waist" might measure 35 or 36 across the actual waistband because of stretching over time. Or it might measure 33 because of shrinkage. The tag is a suggestion. The tape measure is the truth.

Inseam: Measured from the crotch seam to the bottom of the leg opening. This is usually straightforward, but on vintage jeans that have been hemmed, the original inseam length is gone. Check whether the listing notes if the hem is original or altered.

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The Smell Problem

Nobody talks about this enough. Probably because it's awkward. But odor is the most common unpleasant surprise in online vintage buying, and it's almost never addressed in listings.

Smoke damage — cigarette smoke permeates fabric at a molecular level. Light smoke can sometimes be washed out. Heavy, long-term smoke damage is permanent. The garment might look perfect in photos and arrive smelling like an ashtray. There is no reliable way to remove deep smoke smell from heavy canvas or denim. If you're sensitive to smoke, ask the seller directly before buying.

Mildew / musty storage — this is the "grandma's basement" smell. It happens when clothing is stored in damp or humid conditions for long periods. Mild mustiness can often be treated with vinegar soaks, baking soda, or sunlight. But severe mildew means the fabric was wet for extended periods, which weakens fibers even if you can't see visible damage yet. That jacket might smell fine after treatment but start developing holes six months later because the cotton fibers were already compromised.

Body odor / sweat stains — particularly in the armpit and collar areas. On workwear that was actually worked in, this is common. Light deodorant staining can sometimes be treated. Deep yellow armpit stains on a white or light-colored garment are essentially permanent.

Mothball smell — means the garment was stored with naphthalene or paradichlorobenzene. The smell dissipates over time with airing, but it can take weeks. Not permanent, but unpleasant.

What to do about it: Ask. Seriously, just ask the seller: "Does this item have any odors — smoke, mildew, mothballs, or anything else?" A good seller will answer honestly because they don't want the return headache either. A seller who dodges the question or says "I don't notice anything" while selling 500 items from their smoke-filled garage is a red flag.

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Photos: What to Look For (and What's Being Hidden)

Online vintage buying is primarily a visual exercise. You can't touch the fabric, check the weight, or smell the garment. You're relying entirely on the photos to evaluate condition. So you need to read photos like a detective.

Count the photos. A listing with 2–3 photos is hiding something. A thorough listing should show: front, back, close-up of the tag/label, close-up of any notable details (stitching, hardware, embroidery), and photos of any flaws. For jackets, you should also see the lining and the collar (where wear shows first). For jeans, you should see the waistband, pockets, knees, and hem.

Check the lighting. Bright, even lighting reveals flaws. Dark, moody, or backlit photos hide them. If you can't clearly see the color and condition of the fabric, the lighting is doing work for the seller, not for you. Colors can look dramatically different depending on whether the photo was taken indoors under warm bulbs or outdoors in natural light.

Look at the collar and cuffs. On jackets and shirts, this is where wear shows first. Fraying collars, pilling cuffs, and stretched-out necklines are common on well-worn vintage and they're often not visible in a full-body shot. If the listing doesn't include close-ups of these areas, ask for them.

Look at the armpits. On lighter-colored garments, this is where staining lives. If you can see yellowing or discoloration in the photos, it's probably worse in person. If you can't see the armpits in any of the photos, that's intentional.

Check the zipper area. On jackets, the zipper is one of the most common points of failure. A vintage Carhartt with a blown zipper is worth significantly less and costs $15–$30+ to repair. If the jacket is photographed unzipped in every photo, ask whether the zipper works.

Look at the hem on jeans. The condition of the hem tells you a lot. An original, unaltered selvedge hem on Levi's adds value. A chopped, unfinished hem means someone cut them. A professionally hemmed pair with a chain-stitch is fine. Each of these looks different in photos, and the listing should be clear about which you're getting.

Be wary of AI-enhanced or filtered photos. As we mentioned in our reseller post, some sellers are using AI tools to enhance listing photos — smoothing out flaws, correcting colors, making fabrics look cleaner than they are. If every photo looks studio-perfect but the price is suspiciously low for the claimed condition, be skeptical.

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Questions You Should Always Ask

Don't feel awkward about asking questions before buying. Good sellers expect it and appreciate informed buyers. Here's your checklist:

"Can you provide pit-to-pit, body length, and sleeve measurements?" — If they're not already listed. Any seller who won't measure a garment for you isn't serious.

"Are there any odors — smoke, mildew, or musty storage smell?" — The question alone signals that you'll return the item if it arrives smelling bad, which incentivizes honesty.

"Does the zipper work smoothly?" — On jackets. A sticky or broken zipper is a deal-breaker for many buyers and a costly repair.

"Is the hem original or has it been altered?" — On jeans and pants. Affects both value and inseam accuracy.

"Can you take a close-up of ___?" — The collar, the cuffs, the armpits, the lining, whatever area the existing photos don't cover. A reasonable request that any honest seller will accommodate.

"What's the tag say for country of origin?" — On workwear brands like Carhartt and Levi's, "Made in USA" vs. imported changes the value significantly. This should already be in the listing, but if it's not, ask. A seller who doesn't know (or won't say) is a red flag.

"Can you describe the condition of the lining?" — On lined jackets. The exterior can look great while the lining is shredded. This is common on vintage Carhartt blanket-lined pieces and it's rarely visible in standard photos.

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Understanding Condition Language

There's no industry standard for condition grading in vintage resale. Different sellers use different scales, and the same words mean different things to different people. Here's a rough translation guide:

"NWT" / "New With Tags" / "Deadstock" — Unworn, original tags still attached. This is the gold standard. But verify: are the tags actually original to the garment, or were they reattached? Does the item show any signs of storage damage (yellowing, musty smell, fold marks) despite being "new"?

"NWOT" / "New Without Tags" — Claimed to be unworn but tags are missing. Harder to verify. Could genuinely be new, could be lightly worn. Judge by the condition of the fabric, soles (on boots), and high-wear areas.

"Excellent" / "Near Mint" — Very light wear, no significant flaws. This should mean clean, structurally sound, all hardware working, no stains or damage. If a seller says "excellent condition" and the photos show fading, collar wear, or small stains, their standards are lower than yours.

"Good" / "Very Good" — Honest wear. Some fading, maybe minor pilling, light marks. The garment is fully functional but clearly lived in. This is where most vintage workwear lands and it's perfectly fine — these are clothes that were built to be used. Just make sure the specific wear is described, not hidden behind vague language.

"Fair" / "Vintage Wear" — Noticeable wear, possible repairs, fading, some damage. At this grade, you should expect clear descriptions and photos of every flaw. The price should reflect the condition. This grade can be perfectly acceptable for workwear you plan to actually work in — you don't need a museum piece to wear on a job site.

"As-Is" / "For Parts or Repair" — Something is meaningfully wrong. Missing hardware, broken zippers, significant damage, heavy staining. These can be worth buying at the right price if you know what you're getting into, but never at "good condition" prices.

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The Return Policy Check

Before you buy anything — especially anything over $50 — check the return policy. This sounds obvious. Most people skip it anyway.

eBay has a strong buyer protection program. If an item arrives "not as described," you can open a case and eBay almost always sides with the buyer. This makes eBay one of the safer platforms for buying vintage online, despite its other issues.

Depop and Poshmark have buyer protection for items not as described, but the dispute process can be slower and less predictable.

Etsy varies wildly by seller. Some offer full returns. Some offer none. Check before you buy.

Instagram and Facebook Marketplace — essentially no protection. If you pay via PayPal Goods & Services, you have some recourse. If you pay via Venmo, Zelle, or PayPal Friends & Family, you have none. Never pay through Friends & Family for an item from someone you don't know, no matter how good the deal looks.

Independent Shopify stores (like ours) — the return policy is whatever the store sets. Read it. A store with a clear, fair return policy is telling you they stand behind their descriptions. A store with "all sales final" is telling you something too.

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Start Small, Learn the Brands

If you're new to buying vintage online, don't start with a $200 grail piece. Start with a $30–$50 item from a brand you already know. Get a feel for how the brand's vintage sizing compares to modern. Learn the tags. Get comfortable asking sellers questions. Figure out which sellers and platforms you trust.

Once you've bought a few pieces and understand how the process works — how to read measurements, what to ask, what to inspect when it arrives — you'll have the confidence to go after the bigger, rarer finds without getting burned.

The best vintage buyers aren't the ones who get lucky. They're the ones who did their homework. We've published guides for dating Levi's, understanding Carhartt styles, and knowing the Prison Blues story. The more you know about what you're buying, the less you have to rely on the seller to tell you.

Knowledge is the best return policy.

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Quick Reference: The Pre-Purchase Checklist

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