What To Wear With Your New Jeans

Most people put on their jeans one leg at a time. And, hey, there's nothing wrong with the K.I.S.S. approach to denim. But, we also believe that simple never has to mean mundane. In fact, with a bit of sartorial savvy, your most easy-to-grab and timeless closet power-players can also be your most exciting. And, since new jeans and autumn go together better than apple cider and, well, also autumn, we're helping you slip into every new fall denim trend you're already obsessing over.
Not that you need to ditch your tried-and-true skinnies. But, this season, try experimenting with a few more intrepid indigo pieces — like the girlfriend jean, the boxy jacket, and even the cropped flare. We promise, the new styles are nearly as no-brainer as your go-to pair, but the style payoff is way more plentiful. Ahead, a complete how-to on this season's most brilliant denim silhouettes.
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The Overalls
The farmer-friendly style gets translated for fall with some easy, playful layering. A boxy graphic sweater and slim turtleneck complement the onesie's thinner straps.

Richard Chai Love, Wine/Navy Chalk Top Furry Plaid Relaxed T-Shirt, available at Pas de Deux NYC.
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Opt for a thick-soled lace-up for a look that's casual enough for crunching leaves during a weekend getaway, but will also work well for afternoon hot toddies with friends. The ankle socks are also a sweet (but not juvenile) touch.
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The Denim Pencil Skirt
The pencil skirt has become so commonplace in an office-ready wardrobe that it frankly starts to feel a bit yawn. But, the denim version breathes new life into a classic trend.
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This fall's return of the early aughts' popular, knee-length, buttoned-up style feels fresh, cool, and like a much-needed casual upgrade to a workwear staple. Treat it as such and style with crisp oxfords, trouser socks, and a smart collared shirt for a look that says you're polished, and game for wherever the work day takes you.

Socks and Ray Ban sunglasses, stylist's own.
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The Patchwork Denim
Patches have an inherently homespun quality. And, while we're all for flaunting your DIY talents — or at least, suggesting you have them — this autumn's patched-up jeans have been elevated.
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In mix-and-match designs, patches are like the sartorial wink on your favorite new "going-out" denim ensemble. Plus, when paired with an equally quirky top, like this super-swingy, fringed number (and its subtle fringe patch!), the whole look is ready for any party night...and, dance floor.

Maki Oh top.
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The Cropped Flares
While the wide, flare jean could be an honorary member of this slideshow, the cropped version is the newest silhouette that's popular this time of year.
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Like other cropped options, this one falls right at the flattering, just-above-the ankle length — perfect for pairing with fall's many heeled booties. Because this silhouette has a slightly wider-leg cut, balance proportions on top with a not-too-oversized sweater. We used a layered bustier to get things a bit more fitted, but feel free to try a belted sweater or anything with an A-line shape to complement the flares at the bottom.
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The Denim Blouse
Sure, the chambray oxford never goes out of style. But, this time, our eyes are on a top that's more out of left field.
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Perfect for those who love the classic fabric but hate conventional style, the quirky denim blouse is a fall essential. Here, we've paired it with, not one, but two other jean styles. Of course, you could wear this top with a pair of skinnies and call it a day, but we much prefer a truly oddball mashup.
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The Boxy Denim Jacket
If your favorite denim jacket and a menswear-like trench had an adorable lovechild, this would be the result.
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Your new jean jacket will add some structure to any baggier fits, but it's not as stuffy or serious as a black blazer can be. Here, with a mechanic's jumpsuit, the model cashed in on two major fall jean trends, too.
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The Girlfriend Jean
While boyfriend jeans and mom jeans have both had their major moments, now the girlfriend jean is taking over. And, you can think of it as the perfect combination of the two silhouettes: a slightly loose, relaxed fit with a straight leg and high waist.
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Make sure this baggier bottom doesn't overpower your own shape. Keep this look simple with a fitted, button-down shirt and a skinny belt to cinch at your mid-section. Perfecto!
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