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Jeans are one of the most essential elements in many American wardrobes. To get an insider’s take on how best to wear them, we enlisted the help of two experts: Bruce Pask, men’s fashion director of T Magazine: The New York Times Style Magazine, and Eleanor Ylvisaker, cofounder of Earnest Sewn and the e-commerce site

Q: How should denim be worn?
Eleanor Ylvisaker: It comes down to dressing for your personal style and body type. I don't think there are any rules aside from not trying too hard and sticking to what works for you. I've seen every possible interpretation, from acid wash to embellishments, done both in a terrible way and a beautiful way. What makes or breaks a great pair of jeans boils down to integrity of design, authenticity in wash, craftsmanship in production and remaining true to denim's classic casual roots. 

Q: What about denim on denim?
Bruce Pask: Why not? I think it's perfectly acceptable, but personally, I like to mix completely different washes, like a dark indigo pair of jeans with a really washed-out denim shirt worn under a blazer. I'm not against head-to-toe denim either, but I think it's a lot of look and not everyone has the confidence to pull it off. Denim should correlate, not coordinate. We don't want men to look like they're wearing a denim jumpsuit.

Q: Why are so many men obsessed with jeans, particularly heritage jeans?
Denim is part of the backdrop of our consciousness. Think of the style icons we grow up revering, like Steve McQueen, Jack Kerouac, Kris Kristofferson—they all had their denim moment. I also think it has to do with how men buy things. When [there is] provenance, men feel more comfortable spending money and paying attention to it.

Q: How attached do people get to their denim?
It is a very personal piece of clothing that acquires a history with the wearer. People who really geek out on their denim, for example, never wash them. I remember a friend leaving his jeans in a hotel room, and when he found out that they had been sent out to be washed, he was inconsolable.

Q: For women, is denim normally considered a starting point for a look as opposed to statement or collectible pieces?
It really depends on the customer, but for the most part, yes—women look for denim that is either a flattering basic or a trend-based statement piece. Personally, authenticity in wash and integrity in design are important to me, but I am also looking for denim that complements my body type and can be a key, versatile staple in my wardrobe.

Q: Denim is such a no-nonsense staple for men. Any tips for styling jeans in more adventurous ways?
Things that started out as styling tweaks have completely infiltrated the way that men in general dress. It’s become quite common to, say, wear a denim shirt under a blazer. The birth of casual Fridays in the ’90s introduced the idea of denim in the workplace. And then it became evening-appropriate. It’s no longer sacrilegious to pair a dressy jacket with denim. I feel like all bets are off.

Q: What trends are you seeing in the women’s denim market?
Summer brings a range of colorful denim for women, and I've seen a lot of well-worn jean jackets. I am loving the denim-on-denim look with faded blue jeans paired with a washed denim shirt. My personal favorite is the 3x1 skinny W.2 jean with a light blue overdye. It works perfectly for the pastel palette emerging this season.

Q: And what is the rule of thumb for buying jeans?
Denim grows with your body and with wear, so you want to make sure the fit is snug enough to allow for stretch, but not so tight that you have spillage over the waistband. I think your body type should be the first thing that informs your purchase. Stick to what looks right on you and then work from there. Men’s jeans often come in lengths, but this is less common for women’s, particularly at the higher end. What to do? You can always shorten a jean and re-attach the hem, but the proportions are off on many fits. On a boot-cut or flare jean, for example, the narrowing at the knee will hit the wrong spot. That’s why I think it’s smart to invest in custom-fit jeans if you are an avid denim wearer.


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