What to Tell Your Tailor: Vintage Jeans with a Modern Fit

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For most people, experience with tailoring denim starts and ends with getting a pair of jeans hemmed at the local dry cleaners. But especially when it comes to vintage jeans, taking the extra time to get a perfectly worn-in pair altered by someone who knows what they’re doing is your best chance at creating your new favorite jeans — for a fraction of the cost you’d spend at one of those fancy re-worked denim sites.

Sure, you could join a waitlist to spend $275 to $390 on a pair of Levi’s that have been tapered, patched, or slashed into modern styles. Or you could find a pair on eBay or at the Goodwill for $10, take them to your tailor, and never look back.

According to Alice Wells of Kindred Black, the easiest way to give vintage jeans a modern look is to taper the legs. “We suggest taking the jeans to your favorite tailor and have them narrow the thigh and give the leg a slight taper, bringing in the ankle, for a skinnier fit.”

Photo: Driely S.

Emily McIntosh, director of operations at Denim Therapy, agrees — but the options don’t stop there. “We have made many a ‘90s bell-bottom into a straight leg. It's also common for women to bring in loose vintage jeans or even vintage mens jeans and have them taken in at the waist for a more flattering ‘Mom jean.’ If you want to get really up to date, you can add custom patches or move your back pockets around similar to what's been seen on the runways in recent seasons.”

While you can take your jeans to any neighborhood tailor and get just fine results, McIntosh recommends using a specialist for the best outcome. “Employees will be up-to-date on the latest styles and will have a good eye for fit. The seamstress will understand how to maintain the special qualities of your jeans that you don't want to lose during alteration.”

This method is especially helpful if you’re doing your denim shopping online, without a chance to try your jeans on before you pull the trigger. Because most pairs have been washed, worn, and stretched out or shrunk by the previous owner — not to mention the fact that styles fluctuate from year to year — ordering a size that’s worked for you in the past won’t necessarily fit the same way. It’s likely that you’ll need a tailor to tweak the fit for your body.

Photo: Driely S.

So, how much will a trip to the denim tailor cost you? It’s really going to depend on the fit and your desired changes. While a hem change will run you around $15–$25, a full resize can be $110 or more.

If you want to keep things simple (and wallet-friendly) stick to changes in the leg. According to Wells, “legs are easy to adjust and tweak — at the end of the day, the most important part of a good fit is finding a pair that perfectly (and snugly) hugs the butt.”

Here, we’ve outlined four popular styles that will bring your vintage jeans to the next level.

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Slim-Fit “Boyfriend” Jeans

The goal: A mid to low-rise skinny fit with a little extra room throughout and a straight leg.

Start with: Any relaxed fit, loose-fitting, or oversized men's jean. Levi’s 501 and 505 are good options.

What to change: Bring in the waist if needed, and make the leg a little more fitted throughout.

Tip: Denim Refinery’s Janet Sung recommends paying close attention to the pocket size when you’re choosing a pair to make more fitted. “Any disproportion between the pockets and your bottom will only become emphasized.” And if the hem is distressed, consider keeping it that way.

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Modern Mom Jeans

The goal: A mid to high-rise jean that’s more fitted through the waist and hips, (avoiding that blousy, unflattering thing around the crotch and thigh in actual mom jeans) with a relaxed leg and slightly tapered ankle.

Start with: Any relaxed fit jean that hits at a mid to high rise. Levi's 550, Levi's 501 from the '90s, Calvin Klein jeans from the '90s are all great options.

What to change: Make the thigh and hip and little slimmer, and make the taper through the ankle less intense.

Tip: According to Eileen Nunez of Alteration Specialists, “to avoid the excess fabric at the hip and crotch, we will have to taper through the pocket and possibly take in the seat. If the waist is big, we can also take in the waist.”

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Kick Flare

The goal: A mid to high-rise jean with fitted hips and thigh, and a slight flare cropped above the ankle.

Start with: Any flare or bell bottom pair — could be Levi's 512 or 517; Wrangler or Lee boot cut; Calvin Klein's from the early '80s, or even Mud jeans from the late ‘90s.

What to change: Crop and hem just above the ankle, and adjust fit as needed.

Tip: If you’re starting with a jean that fits you well through the waist, hip, and thigh, this is an easy job for your local tailor. But if you’re starting with something that needs tweaking, Nunez says “this will require taking in waist, seat, hip or thigh as needed in proportion to the flare.”

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Wild Card

The goal: Anything you can dream up. Patchwork, foiling, waxing, or even sewing two pairs of jeans together to make one pair of jeans with two different colored legs — the sky’s the limit!

Start with: Any style of vintage jean.

What to change: You can keep the fit and add an interesting wash, or totally rework/ reimagine the fit.

Tip: For a fully reworked fit it’s best to see a denim specialist, and most are happy to take on a custom job. For changes to the wash or look, check out Denim Refinery’s long list of options, from lasered leopard print to distressing and waxing.