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Timeless Menswear-Inspired Classics for Women

Suit jackets, pants, shirts and more borrowed from the boys


spinner image from left to right tilda swinton then viola davis then victoria beckham
(Left to right) Tilda Swinton, Viola Davis and Victoria Beckham
David M. Benett/Dave Benett/WireImage; Amy Sussman/Getty Images for Deadline Hollywood; Gareth Cattermole/BFC/Getty Images for BFC

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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spinner image left actress diane keaton in the movie annie hall right actress marlene dietrich in the film morocco
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

spinner image Grace Karin Women’s Waistcoat Vest in Blue Pinstripe; Double-Breasted Slim Blazer in Pinstripe Wool Flannel; Karl Lagerfeld Paris Women's Metallic Pinstripe Pants in Black/Gunmetal
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

spinner image The Cotton Long Trench Coat in Beech; Belted Cotton Twill Field Jacket in Birch Tan; Women’s Classic Lambswool Pea Coat in Navy
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.

Boyfriend shirts

spinner image Classic Fit Oxford Shirt in Bath Pink; Garcon Classic Shirt in Stripe Cotton Poplin in Regal Blue; Executive Blue and White Fine Stripe Fitted Shirt - White Collar and Cuffs
Left to right: Classic Fit Oxford Shirt in Bath Pink ($128, ralphlauren.com); Garcon Classic Shirt in Stripe Cotton Poplin in Regal Blue ($70, jcrew.com); Executive Blue and White Fine Stripe Fitted Shirt - White Collar and Cuffs ($79, hawesandcurtis.com)
Ralph Lauren; J.Crew; Hawes & Curtis

You can’t go wrong with a crisp cotton shirt, solid or striped. A white collar and cuffs up the formality a bit and conjure images of Wall Street wizards. Tucked into a skirt or trousers for a business-like appearance — or untucked with jeans, chinos, joggers and other casual pants — a boyfriend shirt will become your BFF.

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Tuxedo dressing

spinner image Court & Rowe Satin Tuxedo Stripe Pants in Blue Night; Barathea Italian Wool Tuxedo Jacket in New Off White; Tuxedo Shirt in White
Left to right: Court & Rowe Satin Tuxedo Stripe Pants in Blue Night ($99, nordstrom.com); Barathea Italian Wool Tuxedo Jacket in New Off White ($250, bananarepublic.gap.com); Tuxedo Shirt in White ($38, www2.hm.com/en_us)
Nordstrom; Banana Republic; H&M

In my opinion, a tuxedo in either black or ivory is worth spending some serious money on. Why? Because it effortlessly solves the age-old question of what to wear when the invitation says black-tie. A woman wearing a tuxedo with strappy sandals, undone hair and red lipstick is one of the most seductive looks I can think of for women of all ages. It shows that you are worldly, sophisticated and self-assured. You can also break the suit up. A dinner jacket in black or white looks great over a black base for a cocktail party. A tuxedo pant with a side stripe pairs beautifully with a black cashmere crewneck or a white pleat-front tuxedo shirt. A tuxedo shirt on its own takes jeans to the next level of chic.

Natty accessories

spinner image Oversized Runway Gold-Tone Watch; Handmade Authentic Panama Hat/Unisex; The Vernon Loafer in Leather in True Black
Clockwise from left: Oversized Runway Gold-Tone Watch ($275, michaelkors.com); Handmade Authentic Panama Hat/Unisex ($87, amazon.com); The Vernon Loafer in Leather in True Black ($158, madewell.com)
Michael Kors; Amazon; Madewell

A big gold watch is one of my go-to everyday accessories. It dresses up your look instantly, especially when worn with your sleeves pushed up. When I’m on the go but want to take a step up from sneakers, a classic black loafer or tuxedo flat does the trick (preferably without socks). For anyone living in warm weather or traveling in the tropics, a woven Panama hat packs serious attitude — as well as sun protection — and is much more elegant than a floppy-brimmed hat or baseball cap. Classic Ray-Ban aviators or Wayfarers are also personal favorites.

Final tip

Don’t be afraid to shop in the actual menswear or boys departments (if you are petite.) The prices may be substantially less than similar items created for women. I’m particularly fond of Brooks Brothers and Gap men’s striped cotton broadcloth pajamas with contrast trim. If they are too long, simply roll the hem — or just wear the top.

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