Tricked-Out Cargos
It's been a long uphill battle for cargo pants, but after years of being the official pants of frat bros, they've fully rebuilt our confidence in them as practical and stylishly rugged pants they were always meant to be. You know by now to buy 'em slim, but this season take the extra step by picking up a pair that's got extra details, from thigh-placed zippers to ankle buttons and beyond.
Ralph Lauren Cargo Pants, $185
The 2.0 Bomber Jacket
Last year, we told you that a military-inspired bomber jacket was the one to get. We're still saying rep the bomb squad, but now that you've got some experience under your belt, it's time to upgrade to something not so standard issue (but don't get it twisted—we still love a good surplus bomber). Reach for one with newer, fresher colors and fabrics, like this one navy blue velvet. Dark jeans are fine, but just now that the whole "don't wear white after Labor Day" thing doesn't apply to denim.
Louis W jacket, $690
The Sneaker That's Also a Boot (a.k.a. The Boot That's Also a Sneaker)
The rise of sneaker culture means there are more cool kicks than ever before. But that also means things can get confusing quick. Instead of chasing every cool kid style, find a pair that can do two things at once. These high-tops combine the shape of a futuristic boot with the comfort and weight of a modern day running shoe. The best way to show them off is with a pair of jogger pants, but to keep your look from getting too gym-inspired, ground the look in a classic jean jacket.
Adidas sneakers, $165
The Throwback Track Jacket
The staple of 1970s high school locker rooms and off-duty mob boss closets has finally entered the 2010's in a new way. Designers like Burberry and Gucci are making 'em at the high end, but you also can't go wrong with the original, whether it's a three-striper from Adidas or a logo-sleeve version from the polo shirt masters at Fred Perry. Pair these more tailored tops with looser-fitting trousers and a pair of fresh white tennis shoes. It's a look that will feel as comfortable as wearing a full sweatsuit, but you won't look like an extra on The Sopranos.
Freddy Perry jacket, $95
The Statement Hoodie
In the first few weeks of early fall, when your hoodie can act as your sole piece of outerwear, you've got to make it count. And don't be shy about making a statement—in fact, we're going a step further to say you should literally buy a hoodie with graphic text so everyone knows whatever motto you're about right now. And since the vibe has its roots in the skate world, your best bet is to wear it with some Dickies-inspired trousers and a classic pair of sneakers.
Alexander Wang hoodie, $450
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