How to Wear Menswear Without Spending a Dime: Plus 6 Inspiring Looks!

by Sammy in 3 Comments — Updated November 3, 2019

Hello, fall weather! Hello … new style! The weather is turning cooler, the sun is setting sooner and I’m seeing a whole lotta industrial ankle boots, knitted tights and distressed denim hitting the streets of New York.

What I’m not seeing, however, are girls experimenting with menswear. This is sad for two reasons: Men’s style has hit a high point lately, thanks to shows like Mad Men popularizing the simple genius of a great suit and crisp white shirt. Additionally, every girl with a boyfriend or a couple of guy friends has access to a wardrobe to borrow chic menswear pieces. Well … that is, if your guy friends/boyfriend allows you — which if you follow my advice below, he will!

I was recently asked to style a shoot on wearing menswear — most specifically, incorporating bow ties, ties and caveats into an outfit that still feels pretty and feminine. It’s a tough middle ground to reach. How do you rock a tie without looking like you’re trying to dress like a boy, or wear a bow tie in a non-distracting way to your corporate job in midtown?

Being creative — especially when it comes to playing with the androgynous look — doesn’t have to be limited to us bloggers.  Read on for my advice on how any girl can add some “man” into her wardrobe with pieces that already exist in her wardrobe — plus a few extra elements that are easy to borrow and will surely become go-to pieces in your closet for a fresh [and free!] fall wardrobe.

How to Wear Menswear: Look #1

girl wearing menswear
Silk scarf tied as bow tie

TIP: Pull Out That Oversize Blazer

Forgo cropped blazers for one that hits right above your hip. Vintage 80s blazers are typically longer and have more buttons than the average modern jacket. If you don’t own one already, visit your nearby thrift store and grab one for less than $5.

girl wearing menswear
Pair navy blue and muted browns for a fresh fall look

TIP: Pair Knee High Boots with Pants — Not Skirts

The trend with knee high boots is to wear them with knee length skirts. This works in cold weather when you need some extra leather on your body to protect you from the elements. But for the sake of dressing like a man, you want to wear pants that don’t stick to your leg, and as explained above, the best way to stay feminine with a baggier-than-normal bottom is create contrast with a cinched-to-the-skin boot paired with baggy-in-the-hips wool or cotton pants.

TIP: Wear a Vest Alone

Maybe the vest came with a suit/skirt combo that you’d never wear as a 3-piece work outfit — so don’t. Rather, wear it alone with a white or black low-cut undershirt below, tight enough to stay close to your body while covering all the areas you’d want covered, like your chest or lower stomach/back.

How to Wear Menswear: Look #2

girl wearing menswear
Keep brights in the same color family

TIP: Borrow Guys’ Ties They Hate or Call “Douchey”

Guys all have ’em — the pastel/plaid/way-too-pretty ties that their female relatives inevitably hand them in a box on Christmas morning. And where do they stay? Most likely in the box. Ask your guy friends if they’re looking to unload any never-been-worn/hated ties. You can inherit them and transform them from douchey to darling … on you!

girl wearing menswear
Use a black dress as your easel, accentuating with pops of color

How to Wear Menswear: Look #3

girl wearing menswear
Double up on one element of the outfit – like lace

TIP: Wear Your Mom’s/Grandmom’s/Aunt’s Funky Hat

Dappy men circa the 60s were fans of work outfit hats — and so are you! Just dig into an older female relative’s closet and you’ll inevitably find one. Try wide brimmed hats in dark navy, gray or brown. Or, as I demonstrate in look #5 further below, try wearing a winter beret. The men in France wear’ em — and so can you!

girl wearing menswear
Grey and black combos work for every complexion

How to Wear Menswear: Look #4

girl wearing menswear
Being playful doesn’t have to be overload

TIP: Tie Silk Scarves Into Bow Ties

You probably have a drawer full of them right now — with no idea how or when to wear them.

Here’s your solution: Take a medium-length neck scarf in muted or brights to pair appropriately with your menswear look. I love juxtaposing brights against dark navy/black/brown for a color “pop” at the  neck.

Tying the scarf is easy — just tie a tight bow, and double loop around your neck if the scarf is a lot of fabric or unusually long. Note: When I refer to neck scarves, I’m not referring to winter scarves to keep your neck warm, but rather decorative scarves worn for the sole purpose of adding some pizazz below that chin of yours!

girl wearing menswear
Focus on one playful element and downplay the rest

How to Wear Menswear: Look #5

girl wearing menswear
Grab your man’s bow tie … you’ll never want to give it back!

TIP: Wear Old Lingerie with Menswear

To ensure that I didn’t look like a 12-year-old schoolboy, I grabbed old lingerie from my underwear drawer to wear as a lace top. You can wear these lingerie tops under blazers or vests to feel more comfortable without exposing too much — but expose just enough lace, and your “I-look-like-a-boy” outfit transforms into “I-feel-like-a-sexy-girl” vibe.

girl wearing menswear
Black doesn’t have to be drab — try black lace, black velvet & other materials

TIP: Borrow Bow Ties from Their Groomsmen Outfits

It’s inevitable in your 20s: Your friends get married. And what else is inevitable? You have to participate in the wedding. While most groomsmen rent their tuxedos, a few do make a new purchase of a colored bow tie or other necessary accessory to “match” the wedding colors. And like douchey ties, your guy friends probably think that red/powder blue/white bow tie is … you guessed it, douchey.

Check your Facebook feed for any “I’m a groomsmen at my best friend’s wedding today” status update alerts — that way you can casually Facebook message guy friends to see if they’re willing to pass you any hand-me-downs from the big day.

How to Wear Menswear: Look #6

girl wearing menswear
Try flashy suspenders for an unexpected touch to workday attire

TIP: Tuck Wide Pants Into Knee High Boots

The skinnies are in, sure, but tucking baggy/wide legged work pants [especially wool or cotton pants] into knee high boots allows you to invent a tapered, stovepipe look without having to physically alter the pant. The baggy top of the pants creates a very cool contrasting line against the skin-tight fabric of the knee high boots.

girl wearing menswear
Creating parallels in your outfit — the red in the suspenders matching the red pants, for example

3 thoughts on “How to Wear Menswear Without Spending a Dime: Plus 6 Inspiring Looks!”

  1. Beautiful! Such great tips, think I’ll spread this on to our fans :)

    Reply
  2. Transvestism for females is both encouraged and celebrated by both the fashion industry and covetous cross-dressing sexist, anti-mail females ( ? ). You can’t dress feminine any longer ? Do you feel inferior why not wearing menswear, i.e. pants & military/ cowboy boots ? Then you are the anti-female chauvinist pig !

    Reply
  3. change the word ” why ” to ” when ” from my preceding comment. Women demand equality , then walk the walk instead of talk; society doesn’t accept male transvestism then it should accept female transvestism; can’t b.s. that equitable ,gender logic .

    Reply

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