Make A Man’s World Your World


My first memory of menswear on women was unquestionably Diane Keaton’s look in Woody Allen’s film Annie Hall. The film came out in 1977, so I believe I first watched it with my mom in the ‘80’s. Viewing the look today, I feel the same about her character’s take on menswear – dowdy, frumpy, unfeminine and not stylish. The baggy pleated pants, a suit vest and that Charlie Chaplain-esque hat, I just couldn’t see how this trend would ever improve, let alone come back with vigor decades later.

In retrospect, I do see some of the charm and the current execution of the trend is a softer and sexier take. So how do you ensure your take on menswear stays fresh and feminine as opposed to hobo chic?  Here are a few simple tips and fresh combinations…

If you go for something oversized like this blazer, pair it with something tailored/fitted or a little sexy. The key is you want it to look intentionally oversized and not sloppy. Take this classic cream blazer and pair it with a sexy and fun print short. This leather shell is gorgeous and keeps the look clean – and the back is sheer so it’s subtly sexy. Finalize the look with wedges in a vibrant hue to bring out the unique design of the short.

1. Haute Hippie, Men’s Tuxedo Blazer 2. Raoul, Metallic Leather Tank 3. Carven, Mountain Print Shorts 4. J.Crew, Martina Suede Wedges

The tuxedo shirt is an absolute favorite of mine. It has that same sexy feel of wearing a men’s dress shirt. Emerson’s take on this look with the pleated detailing and sheer sand washed silk – gorgeous (I own it!). Definitely go bold with the black neck tie it comes with. I love doubling-up on the pleated texture and going ultra-feminine with this bright knee-length skirt. Or keep it more streamlined and go with these classic cropped black trousers. Tie-up either look with Carven suede ballet flats in beige (the bow-detailing at the back is so charming.)

1. Emerson Fry, White Sand Washed Tuxedo Shirt 2. J Brand, Chrissie Slim Trouser 3. Carven, Slingback Bow Ballet Flat 4. Nanette Lepore, Sweet Sixteen Skirt

High-waisted, pleated plants again very Annie Hall and a bit of Meg Ryan’s look in When Harry Met Sally.  Derek Lam manages a certain sweetness with his take on the look. Pair it with a cropped leather shirt to ensure the waist detailing is still visible and some 70’s retro wedges.

1. 10 Crosby Derek Lam, Cinched Waist Denim Carpenter 2. J Brand, Baez Tee 3. Madewell, Streetside Sandal