Menswear Muses feat. Karyn Bailey

March 11th, 2014

Maybe it’s just me, but I find that well-tailored menswear looks just as sexy (if not sexier) on women than it does on men.

The best part is, women have more freedom (and therefore more fun) with fashion styling, making them the perfect muses of classic menswear. Naturally, they take more risks with colors, fabrics, proportions, pattern-mixing, accessories, etc. so their combinations can be very inspiring.

For example, two of my female style icons Esther Quek and Sarah Anne Murray (both international editors of The Rake magazine) are known for their womanly take on sharply tailored menswear. In fact, this colorful separates look was the inspiration behind my “turtleneck undershirts” post. 

I wanted to have some fun with this concept, and play a little dress-up with my beautiful friend Karyn. She’s not typically such a dapper menswear dresser, even though she’s secretly been helping me develop the Articles of Style brand for years. So here I styled Karyn in three classic menswear ensembles – to encourage our female readers to try some classic menswear and remind our male readers to look toward the more fashion-inclined sex for inspiration.

1. Bolo Tie Revolution


Bolo ties are just beginning to trend in menswear (although Alex and I both saw them regularly growing up in the country). It’s a great alternative to a classic necktie, and an easy way to take a grey suit + white shirt combo in a non-corporate direction.

I found this polished rock & leather bolo at a local LA flea market, but eBay is also a great place to score them. If you’re apprehensive about trying a bolo start by trying it loose around the neck, more like a necklace than a tie.


Suit by Hugo Boss, Shirt by Brand, Bolo tie Vintage, Hat by Stetson, Shoes by Saks Fifth Avenue. All clothing available at Saks Fifth Avenue (Beverly Hills and select locations.

2. Old Money Prep


The classics always look good, like a navy blazer, pale french cuff shirt, knit tie, and grey glenplaid trousers.

The tailoring is menswear-inspired, but the accessories (watch, cufflinks, tie bar, umbrella) are vintage men’s pieces from my closet.


Navy blazer by Akris Punto, Pink french cuff shirt by Hugo Boss, Wool glenplaid trousers by Theory, Kilted oxfords by JCrew, Gold jewelry Vintage (Dan’s). All clothing available at Saks Fifth Avenue (Beverly Hills and select locations).  

3. Country Weekend


Another universal combo that will never get old: brown felt hat, tweed blazer, preppy striped shirt/tie combo, dark denim, suede boots.


Hat by Stetson, Tweed riding jacket by Ralph Lauren, Shirt by Saks Fifth Avenue, Tie Vintage (Dan’s) Jeans by Levis, Suede boots by Dolce Vita. All clothing available at Saks Fifth Avenue (Beverly Hills and select locations).

Thanks for reading, and special thanks to Karyn for participating (and putting up with my sh-t). I am a very lucky man to have such a beautiful, worldly, and supportive best friend and bride-to-be.

Yours in style,

Articles of Style

Photography by Alex Crawford.

  • Jorge B.

    Does anyone know what the functional purpose of that horizontal line in the middle of the tweed riding jacket is?

  • LouCaves

    Congratulations Dan and Karyn, be blessed.

    Thanks, TSB.

  • Furious Styles

    I love the second look and pinned it on Pinterest. I’d be interested in that look with a earth tone patent leather lace up heel. Either way, these are great looks!

  • Unseen Flirtations

    Congratulations! I’ve been married 3 – 5 years. (I’ll google it to check the exact dates.)

  • John

    Not sure why there is so much back lash on the “if not sexier” line in the opening paragraph. Dan’s obviously comfortable enough in his heterosexuality or else he wouldn’t be marrying her.

  • Steve O

    Please tell me she has a identical twin sister with super identical amazing style?!? I just may have fallen in love

  • Brent

    I just don’t find women in men’s clothing Sexy at all. Blur out the face and feet and BAM you have a well dress dude. Weird

  • Westley Dimagiba

    TSB’s First Lady has more style than most guys I know.

  • Jorge B.

    Echoing what’s already been said, Karyn NAILS the integration of a feminine touch to menswear. Not sure if I’m the only one who thought this, but her pose in the second picture of look 2 seems like a nod to the way you (Dan) tend to pose in a suit.
    As someone else has commented, I would love to see the reverse of this. I know that there is another article where you did something like this, but that was more of you literally borrowing some of her clothes, rather than putting together looks from “womenswear” (very loose term) inspired clothing intended for men. Perhaps you already own some pieces like that and I haven’t even noticed, you’ve proven many times that you have a very varied (haha) pallette of clothing. I think an article like that would be very interesting. Just an idea… B)

    Best wishes to you and future Mrs. Trepanier, I’m looking forward to seeing your wedding tux! God bless you both.

  • andres

    Congratulations both. Huge follower always. From Berlin!

  • Steven Santander

    Congratulations Dan and Karyn!! Women in menswear is probably one of my favorite things about menswear. A simple silhouette and color palette makes a beautiful outfit with the right attention to detail. Karyn nails it in all the looks here, great job as always!

    • Dan Trepanier

      Thx Steven! I hope all is well brother.

  • LMB

    I’m gonna need you guys to stop pushing the bolo ties. Kthnxbye.

  • Adam

    Touche, as soon as you mentioned it, I remembered that post… could be time for a redux on it though

    • Dan Trepanier

      Yea… that could have been much better. We’ve come a long way. Thanks guys!

  • Owen

    Dan – didn’t you do well ;-) Congratulations to the both of you!

    Karyn looks great in all three looks but look #3 is my favorite. I think it’s the footwear that transforms these looks from masculine to feminine. In my opinion look #2 is not as successful because of the shoes – more like ‘a girl in boy’s clothes’ for want of a better expression.

  • Gazman

    Congratulations on your engagement!

  • Matt M

    Congratulations to both of you. Also one of the better posts I’ve seen in a while. But bolo ties…???? Outside of Texas, never!

  • Zo

    I think my comment didn’t send properly… Anyway, I am delighted to see women in menswear featuring on a pretty high visibility blog like this. Whilst there are lots of us women (mostly butch/ androgynous) rocking this look (and have been for a wile) it’s still good to see. I hate the bolero tie, but that’s just me!!!

  • Zo

    Good to see some women in menswear- there’s actually tons of blogs and tumblrs featuring women (most butch or androgynous women) really rocking menswear. Quite a healthy blogging community in that arena too- one I’m lucky to be a part of!!! I personally HATE bolo ties, but everything else is pretty darn solid.

    Also- congrats on your engagement!!

  • Herbert Morrison

    Tanti auguri Dan & Karen! Very happy for the both of you–best of luck together, now & forever. God Bless! Style for style she’s stunting on you player–hope u can keep up ;)

  • ChrisD

    Makes me want to dress-up my girlfriend.
    Something about glenplaid + hips.. :)

    Great feature!

    • Jeanscuffed

      Ok great so it doesn’t make me feel bad about me peeping the hips too lol

  • Juan

    Congratulations to the both of you! I really enjoyed the piece, as my girlfriend herself is more of an oxford+blazer kind of gal. Looking forward to more of the same!

  • Matt

    Old Money Prep…Wow!! Nice

  • levijyron

    Congrats Mr Trepanier!

  • Brady

    Congratulations on your engagement! TSB has been such an inspiration for not only me, but my wife as well! She’s definitely rocking more menswear these days and this post couldn’t have come at a better time (since I’m trying to convice her to enter the March competition). Hopefully you will see some entries and we can make TSB history

    • Dan Trepanier

      Haha that’s awesome Brady. Looking fwd to those entries! All the best.

  • Jaime B

    Karyn is stunning in menswear, although she would probably look good in pretty much anything! Dan, congrats on the engagement!

    • Dan Trepanier


      Thx Jamie!

  • TO

    Future Mrs. Trepanier looks STUNNING! Liked all the looks, the third especially is adorable and would look great on any woman.

  • Angel Ramos

    I’VE ALWAYS SAID MORE WOMEN STYLE!!! Love this post!!!!!! YES!!!!!!! Incredible showcase of style Karyn.

    • Jaime B

      Now let’s get a dual feature on how marriage has influenced your’s and your wife’s style! Dan, make it happen! Angel, huge fan btw!

  • Adam

    Congrats on the engagement. I’ve seen a few posts around the net with women rocking classic menswear and it always looks good. I’m surprised, you didn’t borrow from any men’s shoes, I know that if they can find the right sizes, some classic men’s shoes actually look better on women as well (see Style Girlfriend’s borrowed from the guys posts, where she often looks at men’s shoes as a stealable item, fortunately my feet are too big for my wife to consider stealing my shoes).

    I think you guys are due for featuring the reverse, with a borrowed from the ladies post, with you guys sporting items borrowed from the ladies (maybe for april 1st…), it could both be serious (because there are items that can be borrowed from their closest and styled in a masculine way and pulled off..) or comical (skirts and heels…).

  • JoeFromTexas

    What do you mean “IF not sexier”?! Do you really need to put an “if” there?

    • JoeFromTexas

      Also congrats on yalls engagement. Though I get a 404 when I clicked on the instagram link… Hope all’s well with the pending nuptials ;)

  • J. Darko

    At last, after some debatable posts, this one is quite enjoyable, refreshing and ‘true to the original spirit’ of TSB – at least, that’s how I perceive it. Well-tailored men’s wear looks on women rather well, unfortunately for the most contemporary fashion bloggers, it doesn’t work the other way around.

  • Guest

    At last, after some debatable posts, this one is quite enjoyable, refreshing and ‘true to the original spirit’ of TSB – at least, that’s how I perceive it. Well-tailored men’s wear looks on women rather well, unfortunally for the most contemporary fashion bloggers, it doesn’t work the other way around.

  • cam

    Congrats on the engagement. I’m curious as to why, in your opinion, the pant silhouette in look 1 works on females but not on males? Look 2 is the tapered fit that has gained the most recent momentum in #menswear as we all know. As you can probably tell from my last few posts, I’m becoming more interested in a relaxed fuller fit. I mentioned in Alex’s feature that I had been recently wearing a pair of slim bootcut jeans. Anyway, just would like to hear more insight from the TSB team. Thanks guys!

    • TO

      Cam- “as you can probably tell from my last few posts”. Is this referring to your comments or did you have a blog or something?? If so please share!

      • cam

        @TO – I meant from my last few comments on this blog. I do not have my own blog. I’ve wanted to submit to the contests but I do not Twitter or FB.

  • Shawn

    First of all, let me start by congratulating you and your fiancee for the new step taken in your life, been there last year and I can relate to the hapinness it brings in a couple. Second, I like all three looks! I’ve always been keen to women in menswear classics, there’s something so seductive about it! Last, I think it’s funny you mention Esther Quek and Sarah Ann Murray, because they’ve been on my top women’s list for a while now. You’re right, women tend to have more liberties when it comes to clothing than we do. Nobody would really care if my fiancee wore something extravagant, because that’s what women do. On the other hand, if I just venture out of my casual smart square, people will give me odd looks, thinking I play dress up or wanting to appear something I’m not. As if you gotta be part of the big 3 (an investment banker, a lawyer or a doctor of some kind) to dress nice.. Shame!

    • Shawn

      Dan, why don’t you make a TSB feature out of your wedding? I’m betting a Tim Hortons gift card that this will be the fashion event of the year, with your many stylish friends among family member! :) Anyhow, I’m sure it will be one hell of a nice day for you! Wishing you both best of luck!

      • Dan Trepanier

        Hahaha well now that you’ve mentioned the Timmies gift card…

  • R

    “Maybe it’s just me, but I find that well-tailored menswear looks just as sexy (if not sexier) on women than it does on men.”
    Please tell me a woman wrote the opener?.?

    • AFH

      It’s an interesting line, though let’s face it – if there was a member of the TSB team who was not 100% heterosexual then there would be……nothing wrong with that.

      • Dan Trepanier

        Hmm. I’m surprised to hear you say that Alan, after your loyal readership for the past few years.

        • AFH

          It is more like disloyal readership lol. The point is that if you were bi or whatever, it would be irrelevant. I think you have misconstrued something.

      • Dan Trepanier

        Apologies, I misunderstood your comment at first Alan. You’re absolutely right. A little diversity would probably be good for us.

    • Loscv29


      • R

        Yes, apparently too many morons could not figure that out…it is what it is…

    • Toby

      Why is it better when it’s a woman implying bisexuality than when it’s a man doing so?

    • Alex Crawford

      In this case I think Dan’s calling the clothes sexy, not the man or women wearing them. That being said, I don’t think it’s a reflection on a guys sexuality if he calls another man sexy. One should be able to observe and appreciate how attractive a member of the same sex is without him or her being construed as gay or bisexual.

      • R

        So you’re confident enough to be sitting at a bar, now in LA, and approach a well dressed guy and say to them “man, you look sexy?”

        • K

          Wow, you’re really proving your masculinity, R! Come on, man. Going up to a stranger, male or female, and opening with the line “Man, you look sexy” is a douche move, regardless of orientation. It is totally different – and acceptable! – for a man to acknowledge that other men can look sexy, also regardless of his orientation.

          • R

            Don’t have to open with that statement, I take that back. Sorry, it’s one thing to refer to a dude and say that looks “dope” so-to-speak. But I would NEVER tell or say to even one of my boys, “you look sexy in that.” Sorry thats just me. Sexy is defined as promoting sexual interest….I have never looked at another man that way. That’s great, because everyone behind a keyboard is always more liberal than they are in public, and tougher, for that matter. But living in NYC, DC, and Miami, I have never heard another STRAIGHT man call another man sexy..

            • MS

              Dude, we get it. You’re a homophobe.

    • Dan Trepanier


      I write all the articles on TSBmen. I’m comfortable enough in my sexuality to say that a man looks sexy. That’s kinda my job.


  • Jeanscuffed

    First, I want to extend a HUGE congrats to the both of you! It’s been a long time coming, and I’m glad you decided to share this moment with your readers. I find that most bloggers tend to keep stuff like this hidden, which isn’t a bad thing, but I find I have more respect when people share their personal lives. Secondly, like I put on your IG, “ABOUT TIME you feature Karyn!” She’s a beauty and makes menswear look as easy as you do. The bolo tie outfit is my favorite one. It goes to show you don’t need tons of accessories or colors to stand out. Classic white, grey, black color palette and bolo and hat.

  • Miguel

    Congrats to both, you guys look good together.
    My wife has been asking me about man type shirts, I’ll point her to this post, thank you guys.

  • ishandev

    Shabash! She does menswear better than me. The old skool gold is proper. Hair is on point in every look. Please tell me she tailored the Look 3 jeans?

  • Paul Kim

    Congratulations to the both of you! Great post!