In an era of gender neutrality and unisex fashion, women styling menswear might feel less-than-revolutionary at this point. But the appeal of the sartorial style — sartor is Latin for “tailor” — remains timeless and is often best accomplished with a good tailor. Traditional menswear is grounded in the art of tailoring and puts an emphasis on quality materials, bespoke fits, and overall elegance, but it is tailoring that truly makes all the difference. “Seriously, everyone needs a great tailor in their styling arsenal,” stylist Meaghan Hartland says.
Core tenets of menswear include dress shirts constructed in crisp cotton, suiting separates like blazers and slacks, and refined accessories ranging from loafers and brogues to a classic watch and leather duffel. While some might be inclined to wear head-to-toe menswear, others find it fun to put their own spin on the genre. Truly, there’s no wrong way to adopt the androgynous look; though it does come down to how you wear it. “For menswear pieces,” Hartland says a tailor is “going to be able to shorten hems and sleeves and take in waists pretty easily,” if you know what to ask for and how to put each piece together.
Ahead, stylists share their menswear styling secrets, leaning on both wardrobe pillars and styling tricks that will stand the test of time.
Balance Your Proportions
“It’s all about balancing the fit of the pieces in the overall, final look,” stylist Jordanna Sharp says. If you’re wearing a slouchy pant, for example, she points to a fitted top and belt to complete the ensemble. “The fitted look on top will balance out the baggier piece on the bottom.”
If you’re interested in adding a menswear element to a dress outfit, Sharp relies on an oversized menswear-style blazer and knee-high boots to bring the two together.
Show Some Skin
If you’re hesitant to style menswear in fear of overwhelming your frame, there’s an easy fix for that. “Showing skin is helpful,” Hartland says. “Sometimes a bit of décolletage or even just pushing sleeves up on an oversized men’s shirt or blazer is great.”
One tailoring piece that can be easy for accomplishing this is the waistcoat — simply unbutton a button on the top or bottom for a flash of skin.
Belt a Boxy Blazer
A boxy or oversized blazer is an anchor piece in any menswear-inspired wardrobe. “I think it’s the perfect mix of menswear-inspired dressing with a sexy feel to it when styled well,” Sharp says. “I would opt for nothing underneath and cinch the blazer at the waist with a belt,” she adds, pointing to straight-leg denim and pumps to complete the look.
Go Full Suit
“I love a proper men’s suit,” Hartland says, sharing that she has a collection of three full men’s suits in her closet (her most used being a vintage Giorgio Armani tuxedo). “I love how versatile a men’s suit is; not only do I wear it together as a set, but am constantly wearing [the] separates.”
If you’re dressing your suit up, she suggests a silk tank and heel, and for dressing a men’s suit down, try a sneaker and tank top. “One of my favorite date night looks is worn as a set with a loafer and just a sexy black bra under the jacket,” Hartland says.
Swap For Men’s Jeans
Another favorite men’s item that’s on constant rotation in Hartland’s closet is men’s jeans. “Mostly vintage Levi’s 501s, but I have a selection from a bunch of different brands,” she says, adding that workwear styles (those crafted with a higher-back rise, reinforced stitching, and extra room in the seat and thigh) are much easier to find in the men’s section.
But before you browse the menswear rack, take measurements of your waist, seat, thigh, and inseam so you can quickly find the jeans closest to your size. (There’s a handy size chart and guide here.) And even if you can’t find a pair that fits perfectly, remember that a tailor can always help tweak the fit to mold to your body. For example: the crotch on men’s jeans is an area that’s notorious for fitting differently on women; a tailor can help adjust the bulky shape.
Slip Into Loafers
Dress shoes like loafers, brogues, and oxfords have a traditional menswear feel about them, so they’re an easy way to channel the aesthetic. They also add an instant dose of polish to any outfit, making it easy to mix and match with different wardrobe separates.
Embrace the Shirt Collar
A little bit preppy and decidedly sleek, there’s no denying the appeal of a crisp shirt collar peeking out from beneath a jumper. While Oxford blue and bright white are excellent hues to keep in your closet, try a pinstripe option to bring in a pattern detail.