Menswear-Inspired Trousers

By Taylor Jarrett
how to pull off menswear inspired trousers

ed note: Next up in our Pulling It Off series: stylist Taylor shows me how to wear the season’s best menswear trousers in a way that feels feminine, not frumpy. Turns out, it’s all about the fit. Take it away, Tay! 

From the moment I first laid eyes on Diane Keaton in Woody Allen’s 1977 film Annie Hall, I knew I’d be forever enamored with the look of women in menswear. This version of my dream girl was far out, she was smart, sharp, and she had wit. All of the qualities I had imagined myself possessing, Annie achieved by just showing up in that Ralph Lauren waistcoat and baggy wheat colored trousers. She epitomized style.

*photos by kate lesueur

Today my definition of style has evolved: functionality is as much a goal as the right aesthetic. When approaching this particular look, I started with a visual goal that captured the idea of menswear, then thought about how the pieces would integrate into a modern woman’s everyday life.


Menswear looks have been hot for a couple of years and don’t appear to be fading anytime soon. Influential collections from Gucci and Balenciaga have filtered through to fashion bloggers and stylists repurposing vintage menswear to create unexpected looks. A reenergized feminist movement has also reminded us all that nothing’s sexier than looking (and being) smart.

A few words that should be in your menswear fashion vocabulary: Single Pleat, Double Pleat, Flat Front, High Waisted, Tux, Full Break, No Break, Cuffs.

The first tip to pulling off this look: Always complement your shape.

  • Whether you have a small waist, wide hips, sturdy legs or a clothes hanger frame, try on lots of pairs of trousers to see which ones accentuate the features you love.
  • A girl with wide hips may want to consider high waisted trousers in order to accentuate her height and create the illusion of a smaller waist.
  • For petite gals, go against the grain and try out a pair of pleated trousers for a vintage Italian vibe (and while you’re at it, pair with some of these stackable vintage rings by Vada Jewelry.)

No style or cut is universal: once you know what works best on you, embrace it and feel great wearing it.

Go “No Break” for summer.

A “No Break” is achieved when the hem of the pants just touches the top of the shoe or ankle. This style is perfect for the summer days ahead, and creates a feminine line even on wider-leg pants.


As the expression goes, black is the new black.

In all seriousness, you can’t go wrong with an all black look, no matter the season. However, there are countless ways to make an all black outfit feel more spring-forward, like this combination Camille is wearing for a night out on the town— Tuxedo Trousers by MM6 that show off the ankle and a slightly sheer and bouncy top by Issey Miyake Pleats Please to complement the playfulness of springtime style.

Embrace the high-low mix.

With menswear-inspired trousers you can accomplish the high-low look by going high end from the waist down, while pairing a vintage tee and a leather jacket up top. Not only is this a way to add instant-cool to your weekly wardrobe; it allows you to invest in just one or two beautiful pairs of trousers that you can reinvent in countless ways.