ESC: Jessica Alba

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Jessica Alba just made a serious case for menswear-inspired outfits everywhere.

Is there anything better than seeing trailblazing women in gender-bending fashions? Nope. And with a 1940s twist? (Think: outfits that mixed comfort and glam and tailored to the nines with tight collars and hemlines.) Genius! This stolen-from-the-boys look is hard to nail down if you don't know what you're doing, so let's go over the basics.

It's All About Balance: If you're going to rock a wide-leg pant, you're going to need to balance it out with something slimming up top. Tuck in your shirt of choice—any white blouse with a collar (embellished or not) will do—and make sure whatever you throw on top of that (i.e. a blazer, sweater, or jacket) hits you right at the waistline of your pants.

ESC, Dare To Wear, Menswear

Low: River Island White Eyelet Collar Shirt, $30; Zara Pleated Cropped Trousers, $40; H&M Imitation Suede Jacket, $30; Forever 21 Ankle Strap Crisscross Sandals, $25

Keep It Cropped: If you're sticking to a cropped pant, everything should follow. Notice the crop on Jessica's jacket—at the waistline and the wrists. The tailoring of the outfit really matters as that's really what menswear is all about. Remember: It's important to be consistent when sticking to the overall theme.

ESC, Dare To Wear, Menswear

Mid: Rebecca Taylor Embellished Collar Shirt, $179; Topshop Wide Pinstripe Cropped Trousers, $75; Mango Double-Breasted Jacket, $120; Steve Madden 'Carrson' Sandal, $90

Choose Clever Colors: Besides the obvious rule of making everything look good together, go for a colorful pant. Then stick to a simple palette of blacks, whites, and navys when it comes to your shirt, jacket and shoes. That will guarantee you an incredibly stylish outfit without having to do much hunting around and/or thinking.

ESC, Dare To Wear, Menswear

High: Miu Miu Embellished Cotton-Poplin Blouse, $1235; Babaton Eckhardt Pant, $145; T by Alexander Wang Cropped Blazer, $725; Gucci Horsebit-Detailed Glossed-Leather Mary Jane Pumps, $740

Shoe Smarts: When you're looking for the perfect shoe, keep things chunky. It's important to have fun with the accessories, especially when it comes to menswear-inspired outfits. They're the only details (other than a dazzling collar) that will really allow you to play up your femininity. Stick to a bold shape and you can't lose.

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