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The Guide to New Men's Jeans After 50

9 ways to do denim right


spinner image man shopping for jeans
Red Blu Productions/Getty Images

Men love jeans as much as we women do. So how come they get the whole thing so wrong so often? There are too many confusing style categories — like trim, slim, regular, straight, relaxed, athletic, classic with stretch, no stretch, plus dozens of washes and denim fabrics — so that may be the problem. Whether due to fear of fashion, conflicting and often confusing information, or indifference, most guys 50-plus wear old, outdated jeans that do their bodies no favors. Here are nine ways for him to get new jeans that look and feel great:

spinner image Hugh Jackman in jeans that fit right at the natural waist
SAEED KHAN/Getty Images

1. Start at the waist

Dudes: You need to know your current real waist size! Hold a soft tailor type tape at your waist — which is above the belly button at the crease your body makes when you bend to the side — or use any length of string to measure your waist and hold that up to a ruler or metal roll tape. Jeans should sit at your waist and not up above or below it or (even worse!) beneath your belly. They should stay up by themselves, even without a belt, and fit not too tight, or too loose. If two fingers can slip into the waistband, that’s ideal.

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spinner image Dennis Quaid in straight dark jeans, tee and sneakers
Desiree Navarro/Getty Images

2. A straight jean with a medium rise works for all

This classic fit always works — regardless of waist size or shape — and looks snappy. The cut is deceptively sleek and provides a little extra room for manly bits at the fly (so no pulling, tugging or wedgies!) and pocket space that comfortably carries a wallet and a cellphone. Legs on straight jeans are uniform in width — the same at ankle, knee and thigh — but that width varies. For a contemporary silhouette that's still comfy, you should be able to grab an inch or an inch and a half of excess fabric at the back of your thigh. Choose a soft cotton blend in a medium-weight denim with 2 percent spandex. And for a hipster variation, choose straight-leg jeans that taper slightly from knees down.

spinner image Forest Whitaker
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3. Straight jeans with a looser fit suit muscular, chunky or husky bodies

Don't let subcategories of straight jeans throw you. They may say regular, classic, relaxed or athletic but are still straight, only with a fuller cut through the seat and legs and some stretch for ease. Slouchy legs are fine, but skip anything too saggy, baggy or stiff (like raw denim). Consider pairing them with untucked button-downs and tees for extra tummy coverage, and add a jacket to up your style game.

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spinner image Cuba Gooding
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4. The darker and more even the wash, the dressier the jean

Medium- to dark-blue and black denim are dressier than light faded jeans for a professional, businesslike or more polished look, day or night. Choose a uniform color with no extreme whiskering (prefabricated pattern creases) or shadow fades. Just add a tailored blazer or vest, a crisp button-down, and ankle boots or loafers. Treat them like dress pants or chinos, but with no ironed creases ever.

spinner image Bruce Willis in distressed jeans with sneakers and tees and leather jacket
Splash News / Alamy Stock Photo

5. Faded, slightly distressed jeans are cool on mature men

While dark, even washes have their own appeal, so do vintage washes. Forget rips and tears and go for broken-in, light to medium blues that look like you've had them for years. They may have been stonewashed or sanded slightly at the seams, knees and thighs during processing to get that exact effect. Keep the style straight and otherwise classic — no flares, bell-bottoms or boot cuts — and add in a leather jacket and your favorite tees, flannel shirts and sweaters like Bruce Willis.

spinner image Antonio Banderas
Europa Press

6. The right length is crucial

This is where it is easy to really mess up. How jeans "break" — where your pants hit the top of your shoe — has changed and there are options. If you're a traditional conservative kind of guy, get your straight jeans tailored to a half-break so they break and crease in front and fall pretty straight to mid-heel in back. And if you're a laid-back gent, casual and cool like Antonio Banderas, let them drape and stack up in a loose fall on the way down before fully breaking front and back. Just be aware that too much width and excess fabric bunching up at the ankles looks too long, careless and sloppy. 

spinner image Jeff Goldblum
Storms Media Group / Alamy Stock Photo

7. Keep cuffing under control

If you're hipster edgy, a half inch to an inch double mini roll looks stylish the way Jeff Goldblum does it. Big wide cuffs are best left to teens and millennials who wear skinny jeans and tapered leg styles.

spinner image Ziggy Marley in dark denim, light blue dress shirt worn out
WENN Ltd / Alamy Stock Photo

8.  You can pair jeans with a denim or chambray shirt

The "Canadian tuxedo" — doubling up denim on top and bottom — has gone from a sometimes trend to a forever "do." Fans include Ziggy Marley. Experiment by pairing old with new and shade differences or even black jeans with a blue jeans jacket.

spinner image Tom Cruise in navy cabled crewneck and toned medium blue jeans
Marc Piasecki/Getty Images

9. Pair jeans with stylish pieces

Keep your jeans look personal and updated with tops and footwear like Tom Cruise. Your favorite jeans can go rugged and sporty with a T-shirt, hoodie and sneakers; edgy by adding a black tee, leather jacket and black Chelsea boots; polished by doing a blazer, button-down shirt and lace-ups or loafers. Keep tees relaxed, not tight, and try half-tucking the front as you layer for less bulk at the waist. Tone jeans to tops and shoes for a longer, taller, sleeker illusion, and add a pop of color with a scarf, shirt or whimsical socks.

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