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.
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.)
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.