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


    “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


    “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


    “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


    “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


    “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
    • Blue oxford by Jcrew
    • Boots by LLBean (purchased at a flea market)

    7. It’s okay to look like your boyfriend


    “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.

    • Lynn

      Hi I stubbled on this article because I have a YouTube channel and I actually love mens inspired looks. I think because it looks sleek and clean and not to many things going on such as with womens fashion. But don’t get me wrong I love style and putting a women’s touch on a menswear. Love what you wrote about and maybe you can check out my site on YouTube – theLPchic thanks!

    • Kaboom

      @tsbmen:disqus i want to share this article with a friend, but the images aren’t coming up. Help! lol

    • Rachael

      Its amazing that this blog started some time ago and now it seems to be getting stronger on a daily basis. Everyday as im heading into work i see so many women wearing a tie or a nice pair of braces with their trousers or skirts. which i dont mind seeing cause i really love the look of braces on a woman and enjoy wearing mine on a regular basis. my latest purchas was seen on geena davis a while back. they are a pair of wide leg trousers which are of a very thin fabric which gives it more of a flowy look and feel to it. they are so comfortable and sexy. They end up finishing around my chest then there are these braces that attach from front to back. also i wear a fitted shirt of any colour to finish the look. I have a good range of braces now and always look for a way to add them to an outfit.these days its not just menswear inspired for women but there are some places that are doing women inspired for men such as wide leg or high waisted trousers and then there is the jumpsuit which is my second favourite outfit to the braces which i also have many of in my closet. in a store i saw jumpsuits in the window and loved them and was very keen to have them but they were for men. I was very suprised to how good they looked. they looked like a nice shirt tucked into a pair of trouser in the same style. And i have seen some guys wearing them and it looks great. almost tempted to grab one for the boyfriend but i think i would end up stealing it for myself.

      to see that but thought they were stunning. they looked like a nice dress shirt tucked

    • Tessa

      I really like her style. She doesn’t look boyish at all, but has found a way to add a wide vary of items to her closet!

    • Anonymous

      I basically live for the Annie Hall, quirky, androgynous, ingenue look! Took bad I have boobs, no seriously, they come in the way for funky men’s dressing. Any chance you can tackle it with an, ahem, wider chest? And sadly, tweed and corduroy don’t seem to be made for thighs that rub together. If only I were built…well…more like a man? ha.

    • kenya

      I have recently stumbled on to your you tube page which led me to ur blog and i have to tell u I enjoy it tremendously.You have given me ideas for my significant
      Other as well as some mens wear inspired outfits for myself. Thank you and your(gentlemen in the video) swagger and confidence is off the chain. Keep up the good work. I look forward to future blogs and videos.
      Take care

    • Schuanne, Stylist

      Great post! As the men took their last steps on the catwalk, I released a menswear inspired post “for the ladies” as well, titled “The ‘B’ Word, Part I”. Check’er out; would love to know your thoughts.

      SR, mine is geared towards a woman pulling off the look despite size (try looks 2 and 3 especially from “The ‘B’ Word, Part II” (link below).


      Styled to Wear


      Great article! I think you present an interesting diversity of women’s styles influenced by menswear. Although this was posted over a year ago, it looks like it’s still quite current.

      Just an FYI, I mentioned your “Menswear Inspired Style for Ladies” article on my blog (and also photographer Alex Crawford).


    • Andrea K. Castillo

      The first and fourth looks are my favorite, and I appreciate this post so much, bc I love to tie menswear pieces into my looks as well. Well done!

    • UTK

      did she just walk out from Gossip Girls?
      Amazing looks!

    • ed sinatra

      raaaaaaaawr what’s her facebook, she is hot.

    • SR

      Only very feminine shape women can get away with this. A broad shoulder, or a wide waist women would be confused with a man. Good for you! you do look great with this look!

    • Chiara

      Menswear-inspired looks are great. My favorite accessory are braces / suspenders, they are the perfect combination of classic look and comfort. That´s why I wear them quite often.

      • rachael

        Hi chiara i totally agree with you that braces/suspenders are a great look that women can take from menswear. i never thought about wearing them til one day trying my boyfriends suspenders on with no one around and enjoying how comfortable they are also falling in love with that look. when they are paired with a pair of black wide leg trousers and killer heels and a crisp fitted white shirt i find that i get so many great comments from men but more so women that want the same look

    • Anonymous

      so stylish, so hot

    • Jen

      These looks are perfection. PERFECTION. Love bow ties as well, am now searching for the perfect one as well as a trench coat and braces!

    • Faye

      Really like this. I sometimes wear a bow tie — inspired by Blair Waldorf style. The hardest part was learning how to tie it. If you’re interested, I found this site that teaches you how to tie a bow tie .

    • Alterations Needed

      This was absolutely amazing. I love menswear inspired womenswear, and try to wear it as often as I can. That girl’s got taste!

    • Anonymous

      I absolutely adore women with this sense of dress. Fantastic post!

      -Patrick B.

    • Elizabeth Fay

      Love it! The first outfit with the necklace and done up collar was especially lovely.
      Like MK said, great idea for the “menswear on a girl” post. Thanks SB.

    • AlexP

      Wow I wish there were more ladies like this! I would like to take you out on a nice date, treat you like the lady you are and all that haha great post though fo real :)

    • Renuka

      Love bow ties, on the ,market for one at the moment…love the tartan selection at westwood for men, any other suggestions??


      • SB

        I’m a big fan of the ties from Pierrepont Hicks . You should check them out.

        Also, Brooks Brothers’ Black Fleece line as well as the ties from their Social Primer collaboration have been quality.

        Good luck on your search for the perfect Bow,

    • Anonymous

      My favorite style is your writing style!

    • James

      By the 3rd picture I fell in love with her.

    • Victor

      Jenilee rocks this look very well.

      But with her body, she should wear clothes that flatter her figuer more and yet are still classy.

    • Paige

      Love these looks! Ties have been my go-to for years now, I’m glad other aspects of menswear for women are getting some exposure. I will definitely be sharing a link to this post on my blog. Thanks for the inspiration!

    • Warren

      Dan –

      Damn, she’s beautiful. Forget what she’s wearing, she could make a paper bag look good. I love that she is doing all of this with mall brands for the most part. She makes it all work. Very nice post. Hope to see more of her in the future.

    • Nt.

      Honestly, this aesthetic is one of the most endearing and unabashedly beautiful looks that exists. This needs to inspire more women.

    • Julian

      What a great post! I like the look with the bowtie and the one with the tie.
      Keep up your good work!

    • Anonymous

      Wow! This is great!!

    • Marlo

      You guys killed it with these looks… it was reblogged so many times all over the web…

      big ups and great styling…

      M A R L O

    • Tizz

      I’m in love.

    • alex


    • Robin

      I love this column! She has some great ideas that look stylish as well as economical. Would love to see her as a regular.

    • NK

      My lord shes on some future wife steez right now. This was inspiring for men and women. Keep up the good work guys I look forward to seeing another post like this in the future!

    • Christian

      What a charming girl. I love girl in two tone shirts and braces. This adds an extra element to this blog….I hope she is a regular. Stylish Women are mysteriously hard to find…

      Best Wishes fellow style bloggers,

      Christian Kimber

    • A.H.

      Now dare I say it. This just might be noted as styling on the men, Jenilee! Absolute unique versatility. 2 thumbs up

    • Jen Smith
    • congrats & keep it coming

      You look great jenny,keep going your style.


    • G

      she is beautiful! awesome sense of style!

    • Anonymous

      She is beautiful.

    • JMRouse

      I have a thing for girls in glasses, so you can guess which one is my favorite. :)

      Don’t be afraid to mix it up with posts like this. Good stuff.

    • Em

      That’s my best friend. She’s amazing :)

    • Henri

      Love this post! Jenilee is stunning! (Dan, if your not dating her, you should be!). Seriously though, this should become a regular feature, it doesn’t only offer inspiration to the female readers, because each of those looks could also be adapted and worn by men.

    • Salomon

      What a great post. Goes to show that menswear is very versatile. Dan, I remember you saying something about undershirts but I can’t seem to find the post. Can you please clarify?

    • Dan

      It might be interesting to add a poll to this post. I’m curious what look would be the highest rated. Maybe something to consider…

      • Paul

        That’s a great idea!

        • Karynna

          Must..have…cashmere…sweater. I’m looking for a cute pair of high wastied, pleated, belted shorts for summer. Something in this color would be so perfect. Have you seen anything like it in your lookings around?

      • Adnan

        Your honesty is like a beocan

    • ben

      this actually may be one of my favorite posts yet.

      i just loooove woman i guess.

      p.s. i swear i wore that last outfit a weekago

    • AC

      Man that wasn’t just for the ladies, i’ll be taking some tips from her too! great post

    • Deraj_G

      Jenilee (what a great name) you are a ridiculously beautiful and stylish woman! That’s really an understatement.

      I’d have to say that my favorite look is the bowtie. I really like the how well all of your clothes fit. I will definitely have to start dressing my girlfriend this way!

      Feel free to make another post dedicated to women. It’s a nice change of pace ^_^

    • VB

      This is how I wished my gf dressed like

    • The Shoe Snob

      Love it!! She’s got some great ‘fits going on and some staple pieces to every man’s wardrobe. Way to be diverse with the blog SB!

    • Sabir P.

      Bravo, Bravo. 1st, Jenilee is beautiful. Secondly, she makes men’s wear look 10x better than it does on most men. Personally, the Brace for Impact and the Check, Bar and trench are my favorite looks. Ties are women are a good look and should be worn more often (most men might feel like they are losing some ground in the office though). Keep up the good work!


      The bowtie outfit is best…very high-fashion..

      Good post

      Stay Fresh Jenilee,


    • The Boss

      The first three outfits look incredible. You’re such a cutie, Jenilee!

      Cheers to pulling off menswear inspired style better than most men!

    • Victor Nevárez

      dear God, she’s gorgeous

    • Richard

      Oh, you need not give any apologies.

      I see i can definitely have some fun with my girlfriend. And that girl is beautiful.

      Yours in style,


    • tayler

      i love this! my boyfriend has been following you for a while. i am so glad that you have decided to explore this style area and give us women some helpful hints for throwning oxfords, bow ties, and button downs into our daily wardrobe. thanks again & keep up the amazing work!!

    • MK

      She actually looks better than you in some outfits :-P
      Jokes aside, it’s easy to like like this, when you’re that beautiful. I like “Layer in the masculine” the best, especially pants and sox combo. Good idea with “menswear on a girl” post!