Timeless Menswear-Inspired Classics for Women

When I was in the third grade, I was allowed to choose an outfit to wear to my grandparent’s big 50th wedding-anniversary party. My mother took me to Saks Fifth Avenue and I picked out a grey and white houndstooth tailored coatdress with brass buttons. Meanwhile, my female cousins (around the same age as me) all wore pastel frilly dresses.

I have always been drawn to tailoring and clothing inspired by menswear. I’m not sure why. Maybe it’s because they feel more substantial? Or because I like the regularity of patterns such as houndstooth and pinstripes versus, say, feminine florals? I just knew that there was something chic about a woman wearing pleated trousers, a pinstripe blazer or a big gold men’s watch.

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Diane Keaton (left) and Marlene Dietrich

Brian Hamill/Getty Images; Eugene Robert Richee/John Kobal Foundation/Getty Images

So many female fashion icons have embraced haberdashery over the years, from Marlene Dietrich, Katharine Hepburn and Judy Garland to Bianca Jagger, Lauren Hutton, Anjelica Huston, Patti Smith, Diane Keaton to current celebrities such as Tilda Swinton, Kate Moss, Gwyneth Paltrow, Viola Davis and Victoria Beckham. Strong women, all.

Classic menswear has a consistency whereas women’s clothing is more subject to trends, which is why menswear-inspired clothes are worthy of investment. You can wear them for years or even decades. And now is the perfect time to shop because many of these items are on sale. Here are some of my favorites:

Dapper pinstripes

Left to right: Grace Karin Women’s Waistcoat Vest in Blue Pinstripe ($33, amazon.com); Double-Breasted Slim Blazer in Pinstripe Wool Flannel ($230, theory.com); Karl Lagerfeld Paris Women's Metallic Pinstripe Pants in Black/Gunmetal ($119, macys.com)

Amazon; Theory; Macy's

Beloved by Victorian British bankers and prohibition-era mobsters, the pinstriped suit signifies both dignity and strength. Whether you opt for a pantsuit or separates (a blazer, vest, or trouser), I guarantee you will find yourself turning to pinstripes again and again. You can go all in with a three-piece suit (but I wouldn’t go so far as adding a necktie, although many women have) — or you can wear the blazer with jeans, the trousers with a silk blouse, the vest over a crisp white shirt or over nothing at all. You can also play the masculine/feminine game by wearing a pinstripe pantsuit with a lace-trimmed camisole and a sexy shoe for evening. (An added bonus: pinstripes are slimming because they cause the eye to travel up and down, especially when worn with heels.)

Military-inspired outerwear

Left to right: The Cotton Long Trench Coat in Beech ($298, everlane.com); Belted Cotton Twill Field Jacket in Birch Tan ($295, ralphlauren.com); Women’s Classic Lambswool Pea Coat in Navy ($249, llbean.com)

Everlane; Ralph Lauren; L.L.Bean

Field jackets, trench coats, peacoats — all originally designed for men in the armed forces — have become staples of many chic women’s wardrobes. An army jacket or trench cinched over a turtleneck and slim pants or a pencil skirt is a timeless, chic uniform. A peacoat makes a commanding look with cream trousers and chunky sweaters. All three look chic with jeans and loafers or flat boots.