For The Ladies: “Menswear Inspired” feat. Jenilee

November 10th, 2010

I’ve been meaning to dedicate a post to our female readers for some time, and that time has finally come.

It’s no secret that menswear inspired looks are trending among fashionable women. What a great combo, bringing together two of my greatest passions: women and menswear – both of which can be hard to understand at times, but with some understanding can help bring out the best in a man.

For this post I decided to feature the very talented and super stylish Jenilee, whose personal style is always unique, interesting, thrifty, and most notably, menswear inspired. “If you peeked into my closet you might think I was sharing it with a boyfriend or brother. Ties. Bucks. Tweed blazers. Braces. Cardigans. Etc.”

Influenced vs. authentic. “There is a difference between wearing men’s inspired clothing and actually wearing men’s clothing. I do both. And some of my favorite looks are a combination of the two. Don’t be afraid to wander into the men’s (or  boy’s) department of any store or resale shop.”

Remember though, it’s masculine inspired, not just masculine. “When wearing a heavily menswear-influenced outfit I usually try to mix it up with feminine items such as heels, skirts, jewlery or lipstick. Makeup and hair are easy areas to add a womanly touch – and remember good posture helps you look less like a man and more like a dainty woman.”

Here are some guidelines (not “rules”!) from Jenilee to help you pull-off menswear inspired outfits.

1. Button Up

“One of the easiest ways to make an outfit look more menswear inspired is to button the collar, while adding a chunky necklace can make the neckline look more delicate. Also, when wearing a men’s cardigan, be sure to pair it with form-fitting tailored pants or a skirt to avoid looking frumpy.”

  • Shoes by Stuart Weitzman (gift from grandmother) ·
  • Pearls by Target ·
  • Ring (heirloom from grandmother) ·
  • Shirt by Gap ·
  • Men’s cardigan (gift from a friend) ·
  • Navy pants by Paper Boy ·
  • Hat by Penguin ·
  • Bracelet by Banana Republic

2. Tie A Bow

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“Pulling off a bow tie can be tricky and doesn’t necessarily suit everybody. When put together correctly, however, it can be a cute way to dress up for an evening without wearing a dress. Pair it with heels and a skirt (or “tuxedo” shorts, as shown here) and be sure to keep it classy: you want to channel classic menswear, not playboy bunny.”

  • Tote by Coach ·
  • Tuxedo shorts by JCrew ·
  • Watch by Timex ·
  • Shoes by Target ·
  • Oxford shirt by Rugby ·
  • Lipstick by Lancome ·
  • Bowtie by Brooks Brothers

3. Brace for Impact

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“Lately suspenders seem to be popping-up everywhere from Urban Outfitters to American Apparel and it can quickly become “trendy” and “of the moment”, which is sort of ironic.

As always, the best things are authentic: stick with braces (with leather fasteners that attach to real buttons) rather than suspenders (often synthetic and/or clip-on) . I actually sewed buttons into these cropped khakis myself.”


  • Velvet Blazer (in hand) by JCrew (resale) ·
  • Shoes Resale ·
  • Pants by Gap ·
  • Shirt Resale ·
  • Braces Vintage

4. Check, Bar and Trench

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“Taking cues from Annie Hall and Gabrielle Chanel; mens’ ties can be a great accessory to break out of your usual feminine routine.

Just make sure the collar fits your neck properly and don’t be afraid to add a tie clip.  As far as matching shirts and ties, I’d say the same rules apply to both sexes (see here for example).”

  • Trench by Banana Republic ·
  • Watch by Timex ·
  • Watchband by JCrew ·
  • Tie by Urban Outfiters ·
  • Tie Clip by Michael Andews Bespoke ·
  • Shirt Resale ·
  • Bag by Dooney and Bourke (purchased at a flea market)

5. Business Socks

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“Try wearing socks with your oxfords instead of tights, and sometimes a canvas weekender makes for a more stylish getaway than a fancy purse.”

  • Weekender by Target ·
  • Shoes Resale ·
  • Shirt and Skirt by Jcrew Resale ·
  • Locket by Tiffany & Co ·
  • Boyfriend watch by Fossil ·
  • Beanie by Urban Outfitters

6. Layer in the Masculine

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“Try pairing a light, girly/flowery shirt with heavier masculine layers to create an interesting contrast.

When choosing denim to pair with men’s classics like Bean or Dessert boots, look for something dark and straight leg – and don’t be afraid of a little color at the ankle.”

  • Wallet by Nordstrom ·
  • Peacoat Vintage ·
  • Jeans by Madewell ·
  • Camp Socks by Jcrew ·
  • Flower shirt by Forever 21 Resale ·
  • Eyeglasses frames Vintage ·
  • Boots by LLBean (purchased at a flea market)
  • · Blue oxford by Jcrew

Blue USA Oxford Shirt

7. It’s okay to look like your boyfriend

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“This look is almost all stolen from a man’s wardrobe, and that’s okay. For my most comfy and lazy days this is my go to outfit.

The most important thing to remember here is to keep a straight delicate posture and female mannerisms. You want to look like your boyfriend, not walk or act like him.”

  • Sweater by Jcrew ·
  • Plaid shirt by Polo Ralph Lauren ·
  • Metalic McAlister boots by JCrew ·
  • Jeans by Gap

Thanks for reading.

Yours in style,

Dan Trepanier

Photography by Alex Crawford.