rachel roy menswear

Illustration: Soyeon Kwon

The Philosophy

As a designer, it is my continual objective to create stylish outfits for women that promote confidence and self-esteem. By dressing like the supreme, sharp, self-assured woman you aspire to be, you are motivating and empowering yourself to actually become that woman. To help you build your own arsenal of masculine wardrobe staples, I’ve created a list of key menswear-inspired pieces that I believe every woman should have in her closet.

The goal when trying menswear is to incorporate one or two masculine elements into your outfit that actually accentuate your femininity. For the right balance, I always throw in at least one feminine touch, such as spikey, pointy heels or a brightly colored accessory. Even something as simple as finishing the look off with a bold lipstick exudes femininity.
rachel roy oxford shirt

Illustration: Soyeon Kwon

The Classic Oxford Shirt

This classic button-down is your wardrobe’s best friend, adding just the right amount of sophistication to any outfit. The oxford is also incredibly versatile, made from an endless array of fabrics to choose from, as well as a variety of colors, prints and patterns.

Play with the various styles until you find your signature, but be sure to have at least one solid, crispy white top in the mix. I am all for branching out to cropped, boxy and tuxedo styles, but having at least one basic white button-down shirt in a traditional structure is paramount.

An important detail I both incorporate into my designs and look out for when filling my closet is button placement. I like my oxford shirts to have a button situated directly under my bra, so that when the outfit calls for a low, unbuttoned look, it shows just the right amount of skin based on button placement. Otherwise, if the button placement opens directly at the bra, you will never be able to achieve the low-cut look that many masculine suits require.

Tip: When mixing prints or playing with color blocking, allow the loud pieces to compete, yet ground them with a solid button-down shirt.
rachel roy blazer

Illustration: Soyeon Kwon

The Goes-With-Everything Blazer

The piece that will most transform the garments in your closet will always be the blazer. Not only does it instantly upgrade any outfit, but it also downsizes your shape.

When you’re shopping for the perfect blazer, try on options in your regular top size, but always size up if the fit is slightly snug, because you can have it taken in but it’s nearly impossible to let it out. You should be able to button the blazer with ease, and be sure that the cross back fits your shoulders, is snug but not too tight, and does not extend past your actual shoulder. If it’s a fitted blazer, there should also be a slight cinch at the waist to create the most flattering silhouette. Look for blazers with a high-cut armhole. At first you may think the garment does not fit or is too tight, but a high-cut armhole frames the body as slender, long, and lean as possible. It gives the illusion of long, lean arms and a narrow back. Find shoulders that are sewn tight and are joined to the arm well, with either a small shoulder pad or rope inside to keep the shape for you. With the right fit, you’ll end up looking and feeling like the smartest person in the room.

Tip: Don’t limit yourself to traditional patterns or colors. After you have your classic colors in check, expand to your favorite print or pattern. For me, it is gold sailor stripe ribbons at the sleeve.
rachel roy trench dress

Illustration: Soyeon Kwon

The Trench-Style Dress

I consider the trench dress to be a feminine equivalent to the men’s suit. The idea behind the shape is that it is designed to promote function, comfort and beauty, and it truly is flattering to all body shapes. I often use a solid trench dress as a blank palette to highlight whatever new accessory I have acquired, because the dress allows a jeweled heel or multicolored necklace to be the main focal point of the outfit and really become the spotlight, especially if the trench is not heavily designed.
rachel roy tailored pants

Illustration: Soyeon Kwon

The Tailored Trousers

Trousers are extremely versatile, infusing a professional, sophisticated office look with just the right amount of cool, boyish style or the epitome of femininity when fit a bit more snug.

Various styles of trousers can flatter different body types; the key is how you alter them to your body.

Classic fem shape: Ensure the rise in the bum has the right scoop for your tush so it lifts and separates, giving the illusion of hours spent in the gym doing squats.

High waisted: The higher the waist, the longer the leg. Ensure the waist is snug enough to hold in the tummy and create a long, lean-looking wall of a torso—the illusion works wonders, especially with heavier fabric. For short-legged girls, taper the ankle and show a bit of skin so the fabric does not overwhelm.

Wide leg: Ensure the fabric hangs straight down from the widest part of your body—usually your low hip. This will give the illusion of long, lean legs. Also allow the waistline to skim your hips, similar to a boyfriend jean; a tight waistline with wide leg pants will add weight. I reserve that shape for the skinniest version of myself only.

Tapered: Good on everyone—add invisible ankle zippers on the inside or outside of the ankle for easy access in and out and to ensure a snug ankle fit.

Cropped: Good on everyone. Mid-calf is the goal. Super easy when you envision Audrey Hepburn and simply channel her, replacing a twin set with your own signature top.
rachel roy accessories

Illustration: Soyeon Kwon

The Right Accessories

When looking for a hint of masculinity, I seek out an equilibrium I can only get through my menswear pieces: oversized watch, loafers, oxford shoes or a handsome carryall. I love eyeglasses, too; depending on your style, they can completely transform your look. I wear them in a way that’s anything but dainty, opting for frames that are bold and strong, and remind me a bit of a 1950s professor. The right accessories can create that necessary harmony between sharp and soft, edgy and classic, whether you’re headed to the office or out for leisure.

Reprinted from Design Your Life: Creating Success Through Personal Style Copyright © 2016 by Rachel Roy. Published by Dey St. Books an imprint of HarperCollins.