A humble youth, a rebellious adolescence, and now years of easy stability: You and blue jeans have a lot in common. Jeans are the most democratic piece of clothing in your closet, but the so-called everyman pants don’t look the same on every man—or in every generation. Maybe Seinfeld’s high-waisted jeans (and high-top sneakers) were okay in the ’90s, but they look dorky today. President Obama, who’s worn frumpy dad jeans in the past, has learned the error of his sartorial ways. With a little guidance, you can do better too.

Rise Above the Fray

Buying jeans with whiskering at the pockets, fading on the legs, and a few minor abrasions is a convenient way to avoid a long break-in period. But if you opt for the distressed look, keep it minimal and choose your scuffs wisely, says Francine Rabinovich, founder of Denim Therapy, a denim repair shop in New York City. If the damage is on areas that distress naturally, such as knees and back pockets, you’re in the clear. But if it’s in odd places, like the shins or thighs, it’ll look fake. “It’s just so inauthentic,” says Rabinovich.

Don’t: Be a Clean Freak

The less you launder frayed and distressed denim, the better. The processing that creates the whiskering effect and fading degrades the integrity of the fabric, so your jeans can wear out quickly with excessive laundering. And when you do wash them, don’t toss them in a dryer and further damage the weakened fibers. Instead, turn them inside out and air-dry them flat, advises Rabinovich.

The Length of Your Shirt Matters

Too short and it looks like a crop top; too long and nobody notices how great your jeans fit. The proper shirt should fall around the top or middle of your back pocket, says Durand Guion, VP and men’s fashion director at Macy’s.

Don’t: Tuck and Run

For every shirt you own, decide whether you plan to wear it tucked. If yes, leave it long. If not, take it to a tailor.

Treat Your Jeans Like Dress Pants

Yes, even your denim deserves a trip to the tailor, says Greg Sato, a Los Angeles designer and marketing manager at Levi’s. “Jeans can be dressed up,” he says. But they won’t look good unless they fit you correctly.

Do: Give It a Spin
Run your jeans through a wash cycle before having them altered. They’re cotton, so they’ll shrink slightly.

Or, Hell—Just Cuff Them

Want to save a tailor’s fee? Just roll the legs up. But the trick only works with selvedge or otherwise stiff denim that already fits great in the waist. And the legs should be narrow—don’t even try it with your boot-cut jeans.

Don’t: Leg Out

An office-friendly cuff just covers the top of your shoe. If your socks show before you sit, the cuff is too high.

Pick Your Cuff

The Single: It’s quick and classic: Just fold up the bottom 1 1/2 inches and crease it.

The Double: Fold it up 1 inch and then give it an extra roll. Go higher for a casual look.

The Messy Triple: Feeling leisurely? Roll a half-inch cuff, double it over twice, and leave it rumpled.