Everybody names the 501. Fewer people can explain why the 505 might actually fit you better — or when a 517 is the right call.
Vintage Levi jeans men is a category that’s broader than most guides admit. The 501 is the default but Levi’s produced 505, 517, 550, 505, 521, and others across the vintage era, each with different cuts and different ideal bodies. This piece covers the three cuts most worth hunting — 501, 505, 517 — with honest notes on who each one fits. Builds on Mens Vintage Levi’s and Vintage Levi’s 501 Men’s; broader pillar at Brand Guides.
The 501: the default
The 501 is straight leg, button fly, mid-to-high rise, full thigh with slight taper to a 16″ leg opening. It fits the broadest range of men’s bodies because the cut is forgiving through the thigh and the straight leg works with most shoe types.
Best for: athletic and average builds, men 5’7″–6’2″, waist sizes 28–38. If you want one pair of vintage Levi’s and you’re not sure what to try, start here.
Where the 501 falls short: men with wider thighs or larger hip-to-waist ratios may find the 501 restrictive through the thigh. If the 501 pulls at the thigh when you sit, you want the 505 instead.
Typical price for 1990s made-in-USA in common sizes: $45–$85. See Mens Vintage Levi 501 on Poshmark for current listings.
The 505: relaxed straight leg
The 505 is my underrated pick. Zipper fly instead of button fly, slightly lower rise than 501 (by about a half inch), and a genuinely roomier thigh that tapers less aggressively to the ankle. It’s the 501 for men who want more room.
The 505 was introduced in 1967 and ran parallel to the 501 for decades. Vintage 505s are easy to find across all the major eras (big E in the 1960s and early 70s, little e after).
Best for: men with wider thighs, larger hip-to-waist ratios, or those who prefer a zipper fly. Also worth trying if you find 501s too restrictive in the seat.
I own a 1988 505 in a 32×32 that I wear more often than my 501s for relaxed days. The difference is subtle but real — less pulling when sitting, more room through the thigh.
Typical price: slightly below 501 equivalents, $40–$80 for 1990s pairs. The 505 is consistently a better value per-wearable-pair than the 501 right now. See Vintage Levi’s 505 Relaxed Fit Distressed Jeans for more specifics.
The 517: bootcut
The 517 is Levi’s bootcut, with a subtle flare from the knee down (about 1.5″ wider at the hem than at the knee). The rise is high, the thigh is moderately roomy, and the leg opening is 17–18″ depending on era.
The 517 is the right cut if you wear boots or chunky shoes regularly, or if you want a slightly more dressed-up vintage silhouette. The flare balances the leg visually over a substantial shoe.
Best for: men who wear cowboy boots, tall boots, or chunky sneakers regularly. Also good for taller men who want a more elongating leg line.
Sizing note: 517s ran big in the waist at some production points. Check flat measurements carefully. I bought a tagged 32 that measured 33.5 at the waistband. Had it tailored down.
Typical price: $50–$100 for 1980s–1990s pairs.
The cuts I’d skip for most buyers
550: the “relaxed tapered” cut from the 1990s. The tapered ankle looks dated to that specific decade. Not timeless.
521: slim straight, but the modern Levi’s 512 and 511 fill this niche better with more consistent sizing.
560, 565: baggy cuts from the 1990s. Occasional hip-hop revival interest but most buyers will find these too oversized for daily wear.
If you’re not specifically hunting these cuts for a reason, stick with 501, 505, and 517.
Sizing across all cuts
Same principles apply across cuts: flat measure, match to your target, don’t trust the tag. The differences between cuts are smaller than the differences between well-fitted and poorly-fitted pairs.
Rough conversion from modern Levi’s size to vintage: subtract 1″ from your modern waist size for 1980s and earlier vintage (vanity sizing drifted larger over the decades). A modern 32 waist is often a vintage 31.
Inseam: vintage pairs were cut longer and meant to be hemmed. Listed inseams reflect current length after any hemming. Compare to your target.
How to test fit without a fitting room
Measure one pair of jeans you already love in every dimension: waist flat across, hip 8″ down, thigh 1″ below crotch seam, knee, leg opening, front rise, back rise, inseam.
Call this your target spec. For any vintage listing, match the listing measurements to your target. Within a half-inch is excellent; within an inch is probably fine; beyond an inch needs thought.
The one dimension I’m most strict about is thigh. A thigh measurement 1″ smaller than my target reliably produces jeans that feel tight when sitting. A thigh measurement 1″ larger looks baggy. Get thigh right and everything else is adjustable.
The three-pair starter rotation
If I were starting over from scratch, I’d buy three pairs in this order:
Pair one: 1990s 501 in your measured size. Budget $60–$85.
Pair two: 1980s 505 for the relaxed day alternative. Budget $50–$80.
Pair three: either an 80s 501 for the higher rise heavier feel, or a 517 if you wear boots. Budget $70–$100.
Three pairs, $180–$265 total, covers most wardrobe needs and gives you a sense of what cut and era you prefer for future purchases.
The honest negative
Vintage Levi jeans men can start feeling like a collecting habit. I went from “I want one pair” to owning seven vintage pairs in four years. Part of it is the hunt — every well-fitting pair scratches a specific itch. Be honest with yourself about whether you’re building a rotation or accumulating variations on the same cut. Seven pairs of 501s that all kind of work is less useful than three pairs of different cuts that each work perfectly.
The verdict
Start with a 1990s 501 in your measured waist. If that fits well, add a 505 for variety. If the 501 doesn’t fit well — especially if the thigh is tight — try a 505 instead as your primary. Budget $60–$90 per pair and factor in possible tailoring. For alternatives to 501, see Vintage Levi’s 512 and Vintage Levi’s 505. For the broader picture, Mens Vintage Levi’s covers men’s vintage more generally. Mens Vintage Levi Jeans on Amazon for reissue alternatives.
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FAQ
What’s the difference between 501 and 505?
501 has a button fly, slightly higher rise, and slightly slimmer thigh. 505 has a zipper fly, slightly lower rise, and a roomier thigh. Both are straight leg.
Which vintage Levi’s cut is most forgiving for larger thighs?
505. The cut is genuinely roomier through the thigh than 501 despite being in the same “straight leg” category.
Is the 517 bootcut too dated?
Depends on the version. 1980s 517s have a subtle flare that reads timeless with boots. 1990s and 2000s 517s had more dramatic flares that read more specifically period.
How many pairs of vintage Levi’s do I actually need?
Two to three pairs covers most wardrobe needs if you choose different cuts or decades. More than that is collecting, not rotation.
