Run the numbers on a $9 thrifted canvas tote carried 140 times and you get about six cents a wear. Do the same for a $38 vintage silk dress worn six times and you're at $6.33. The tag tells you almost nothing. How often you wear it is the whole story. The six examples below use typical secondhand prices and plausible wear counts for half a year. They're illustrations to copy, not anyone's diary.
Cost per wear is the measure worth trusting, because it's the only one that combines what you paid with what you actually did with it. It's simple: price divided by wears.
What counts as a wear
A sensible rule: one wear is one full day out of the house, or one evening event. Trying it on at home doesn't count. Wearing it on an hour-long errand does, and two days in a row on a trip counts twice. Log each one in a notes app next to the price you paid, and the math does itself.
The method has one built-in flaw worth naming: it punishes recent buys. A coat bought in June has had fewer chances than a tote carried since January. Treat any ranking as a snapshot, not a verdict.
Cost per wear, ranked (typical prices, illustrative wears)
| Item | Typical price | Example wears | Cost per wear | New equivalent (est.) | Resale (est.) | Takeaway |
|---|---|---|---|---|---|---|
| L.L.Bean canvas tote | About $9 typical | 140 | $0.06 | $45 | $15 | Best in show |
| Levi's 501, 1994 | About $18 typical | 96 | $0.19 | Check levi.com | About $55 typical | Buy again |
| Navy wool peacoat | About $42 typical | 74 | $0.57 | $450 | $130 | Buy again |
| Dr Martens 1460, used | $55 | 88 | $0.63 | $180 | $70 | Needs breaking in |
| Cashmere crewneck, secondhand | About $24 typical | 31 | $0.77 | $100 | $18 | Watch the moths |
| 1980s silk dress | About $38 typical | 6 | $6.33 | $295 | $60 | Occasion wear only |
| All six | $186 | 435 | $0.43 avg | $1,168 | $348 | About 73 wears per item |
The six, one by one
Prices are typical secondhand figures, estimated as of October 2026, and wear counts are illustrative six-month examples. Resale figures are rough estimates.
Six finds, best to worst value
Ranked by cost per wear in the example above. The last entry is there to make a point, not to be copied.
Best valueL.L.Bean
Canvas tote, without a monogram
A faded monogram is often why a thrifted one is cheap, and stitching can sometimes be picked out. Look for a doubled base and stitched handles. These can take daily use for years.
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Buy againLevi's
501 jeans, 1994, made in USA
One of the cheapest ways to own heavy denim. Worn several days a week, they earn their price fast. A small, stabilized repair at the hem is common and fine.
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Unbranded, vintage
Navy wool peacoat, melton
Heavy melton in a shape that hasn't changed in decades, which is why it's cheap and why it works. Replacing a couple of buttons costs a few dollars. Listings titled "military surplus" are often underpriced.
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Dr Martens
1460 boots, used but not broken in
Buying a lightly worn pair means someone else suffered the painful break-in. Check the sole for heel drag and the leather for cracks at the flex point across the toe; most other parts can be replaced.
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Secondhand cashmere
Crewneck sweater, oatmeal
A pale oatmeal shows every mark, so it needs washing after a couple of wears and gets fewer outings than a navy or brown one would. Lovely fiber; the color is the problem.
Search listingsOccasion only1980s, unlabeled
Silk dress, printed
Beautiful, dry-clean only and useless on a Tuesday. It's here as the control: a real bargain on paper can still be the worst value in your closet.
Search listingsWhat the ranking gets wrong
Cost per wear rewards frequency and ignores pleasure, and that's a real gap. A silk dress can be worth every cent of its $6.33 to the person wearing it, and by any other measure it's a better buy than a tote. Use the number to catch bad habits, not to overrule joy.
The other flaw is timing. A coat bought in July has had a summer of barely any use. Run the numbers in February and it would look far better. Treat the ranking as a prompt to log your own, not as a league table.
What to copy next year
Buy heavy fabric in a plain color, in the size that fits now, and pass on anything that can't go in the washer unless you know exactly where you'll wear it. That's the whole lesson of the math, and it's cheaper to learn on paper than in your closet.
