Here at TheStyleBlogger we love our readers – both male and female alike.
It’s been a while since we did something for the latter, so ladies take a break from trying to improve your man’s style and indulge in some menswear yourself.
We received so much positive feedback for “Menswear Inspired Looks featuring Jenilee” that we decided to run the feature again, this time featuring the stylish and beautiful Helen Weselcouch.
Here, some looks and tips from Helen to help you pull off some menswear inspired outfits.
1. A Womanly Bow
“Just because it’s considered menswear doesn’t necessarily mean it has to look masculine. Bowties have long been considered a staple of menswear but have recently come into their own as a staple of contemporary fashion for both sexes. I like to pair one with a well-fitting oxford and maintain a feminine feel with a delicate skirt or shorts.
One thing to remember with neckwear, especially bowties, is that they make enough of a statement that no jewelry is necessary. Any sort of dangling earring or headpiece will crowd your face and detract from the item itself.”
Oxford and bowtie by Rugby Ralph Lauren. Skirt and belt by J. Crew. Clutch by Lulu Townsend. Vintage Bracelet. Shoes by Lucky Co.
2. Classic V-Neck & Plaid
“One of my favorite looks on a man is a classic sweater over an oxford or flannel shirt and it just so happens that this look translates wonderfully to a woman’s frame.  Button-up shirts and sweaters come in an endless variety of materials and colors, so you can find a combination to suit any taste or season.
I find high wasted bottoms are best to flatter the proportions of my body type with this outfit, but the look would also work with a pair of dark skinny jeans during the day or a tea length skirt at night.”
“Don’t even get me started on hats. There is a hat out there for everybody. Find yours and I guarantee you’ll fall in love with it the same way I fell in love with this vintage number from a quaint second-hand shop on Venice Beach.”
Vintage hat. Shirt and shorts by Rugby Ralph Lauren. Sweater by J. Crew. Trouser socks by Polo. Boots by Franco Sarto.
3. Â Another Prep School Remix
“Even if you’ve never set foot on a tennis court or an Ivy League campus you can still take pride indulging in timeless pieces inspired by preppy Americana.
A boxy “school boy†blazer and oversized khakis are both classic and edgy when paired with menswear inspired accessories and a neutral wedge.”
Vintage sunglasses. Oxford by Urban Outfitters. Blazer, pocket square and Khakis by Rugby Ralph Lauren. Vintage belt. Shoes by J. Crew. Briefcase by David King.
4. Chambray & Pearls, Take II
“I was really inspired by Jenilee’s pearl and chambray look from the last lady-friendly post on The Style Blogger so I decided to put my own spin on it.
A chambray shirt (definitely a must-have for everything from beach BBQs to rooftop cocktail hours) paired with pearls and not-too-short cutoffs can be fun and elegant without crossing into Canadian tuxedo territory.” (Easy on the Canada jokes eh Helen!)
“Wear it with a cardigan and a pair with boyish sneakers for a look that is youthful and flirty.”
Pearls by J. Crew. Sweater by Gap. Chambray shirt, belt and shorts by Rugby Ralph Lauren. Shoes by Converse.
5. Oxford, Cotton Tie, Trench
“It’s no secret that men are fascinated by a women dressed in their clothes, more specifically a classic staple like an oxford shirt or trench.
Pairing a “boyfriend†oxford with a smart tie and trench makes for a perfect rainy day outfit.
And don’t forget that a girl’s most flattering accessory, besides confidence and a genuine smile, often comes in the form of a well-dressed man.”
Vintage men’s shirt. Tie by J. Crew. Skirt by Zara. Trench by Rugby Ralph Lauren.
6. Toe-to-Toe in my Heels
“I love the idea of a smart and sophisticated power-woman who isn’t afraid to go head-to-head with a man in matters of work, pleasure and, of course, style.
A stylish woman can turn any man’s head while simultaneously giving his outfit a run for his money by mixing masculine fabrics, well-tailored separates and menswear-inspired footwear.
Just remember to stay true to some elements that are wonderfully feminine, i.e. bare legs and a killer heel.”
Buffalo plaid shirt by Foxhead Clothing. Blazer by Urban Outfitters. Herringbone Skirt by Urban Outfitters. Watch by Invicta. Bag by Cynthia Rowley. Shoes by Forever 21.
6. Just Blazing
“In my opinion every woman should own at least three blazers; one navy, one black and one that is light in both weight and color.
During the fickle spring months, nothing transitions from a day at the office to a night on the town quite like a cream blazer in a romantic cut that can finish off any outfit.
Add masculine energy with a tie and sleek bottoms or keep it feminine by pairing with a blouse and skirt.”
Sunglasses by Ray-Ban. Shirt, tie, blazer and jeans by Rugby Ralph Lauren. Belt by Express. Shoes by Tahari. Bag by Hype.
Thanks, as always, for reading – and special thanks to Helen for participating!
Yours in style,
SB
Photography by Alex Crawford. As usual, check out some bonus looks and photos in the Lookbook.





















Loved this post. Helen is gorgeous in her outfits. Truly on the button when men find it appealing when women are in their clothes. Keep up the good work
Love that you followed up with a Part II. This makes me want to answer with a post featuring yours truly wearing menswear inspired pieces. This one where I give tips and put together outfits for any woman’s menswear inspired taste will have to do…for now…http://styledtowear.blogspot.com/2012/01/b-word-part-ii.html
I didn’t want this post to end. Helen, let me be your ex-husband?
wow I just found your blog and I LOVED this post!! More please ;)
Cute skull bow tie!
I really love your blog
MORE MORE!!! My whole closet is menswear inspired. I’m also so worried about whether or not I am pulling it off correctly. Love these posts!! Wish I could find a blog that pertains directly to women in menswear.
OMGwala-gwala! I love when women do menswear properly..and it doesn’t hurt that she’s fine as angel shit
She is HOT!!! Looks like some of the models in St. Tropez in the second last picture. I live here and it’s choc-a-bloc of americana done well.
Wonderful feature, Helen looks fabulous. And I was just thinking about requesting that you do feature with the female version of your fashion favorites before I came across this post! Glad I don’t have to now :-) These suggestions are perfect.
I love these, been referring back to this post for a few outfits now. How would readers/SB team tweak a menswear look for a woman to wear to a wedding as a guest — what’s the SB’s take on a more formal menswear look for women? Would you even recommend it, or say stay stick with the dress? Curious what others think about a woman in bowtie/tie & skirt for attending a black tie or cocktail event.
Would love to hear from everybody! Thanks.
Hey Lauren! If it were me I would avoid any notion of formal menswear all together unless you want to look like Marlene Dietrich in the film “Morocco” (which is an amazing look don’t get me wrong but might be a tad too costumey for a wedding). Instead, go for something 100% ladylike but with a masculine twist. Take a cue from the Brits and get a little top hat shaped fascinator or look for dresses with a bowtie detail (there are tons out there…I LOVE This one http://bit.ly/kp12Nl).
Shoes are also a great place to have fun with changing up your look. Menswear inspired shoes are popping up everywhere and it’s a trend that you can definitely get behind for a wedding. An oxford inspired shoe looks amazing as a flat or as a heel and you can get them in about a zillion materials and colors to match whatever else you’re wearing.
Have fun!
I think it can be done. I’ve seen women who work for Thom Browne look sharp as a tack in a dark suit and skinny tie.
If you’re going to do it, make sure it flatters your body type.
I also think both Jenilee and Helen had an outfit that can easily be adapted to black tie.
Jeni, with a black bowtie and her “tuxedo shorts” (and perhaps a fitted/cropped jacket to go with):
http://www.thestyleblogger.com/wp-content/uploads/2010/11/4a-copy.jpg
And Helen in her last look, perhaps without the skull and crossbones and a more formal pant:
http://www.thestyleblogger.com/wp-content/uploads/2011/06/15.jpg
Don’t be afraid to give it a try – with the right attitude (and styling) you can get away with just about anything ;)
If you do it right, I think you’ll stand out even more than the pretty dresses.
Cheers,
SB
these are such classic looks. glad i stumbled upon some new inspiration.
http://the-champagnelife.blogspot.com/
oooh i love these, dan. thank you so much. do more please. the girls n i appreciate your talent
helen, you definitely look hot
Thanks so much for the great post. I really enjoyed reading it. I’m so glad for more information on Casual clothing.
http://www.clothingobsession.com/
She is very hot hot, hot, classy, pretty, fashionable, elegant, beautiful etc……Congratulations on you blog and new enterprise!!!!!! excellent work
This is a great photo spread and story, Style Blogger! We love ladies wearing “our clothes”. Helen sure has some style too!
This girl is super attractive omg, and dressing well just makes her even hotter
Just blazin… (nice Nicki Minaj reference) great layout. Good luck with the line.
Love these looks! I’m so into the slouch socks with the boots. I also like them with Mary-Jane type heels!
Sorry to strike a discordant note, but there’s so much women’s fashion coverage, and you have so much more to offer for men, I suggest sticking to your (male) knitting.
hot looks, hot girl
http://thetastelevel.blogspot.com/
Dan,
Are you styling these looks ? or they her own ? In anycase, love it all.
I hope my next girl looks as well put together as Helen. Nothing worse than always being better dressed than your lady.
VB
I loved all the looks. I’ll have to try the chambray and pearls some time. The picture with Townsend was very cute. They look great together.
Clearly a very pretty girl and I’m a big fan of looks 4&6. But something about a woman in neckwear screams chain restaurant hostess/waitress to me. Personal preference for neckwear would be to see a ‘softer’ look like a play on an ascot or bandana. Nonetheless, nice work on continuing to present different points of view.
I’ll definitely go WEINER on this beauty!
She made my day!
Nice outfits, beautiful woman, what more can i say, accessorized with a Muskoka chair. Just perfect.
I want a girlfriend like her ;) Love her looks.
http://man-you-are-in-fashion.blogspot.com/
Townsend better get a ring on it.
Haha! She is pretty amazing… I’m a lucky man
Nice post for the ladies! In number 5, what belt is the guy wearing?
looks great helen, and guys!!
-LBR
I wish my girl friend dressed like that
This girl is beautiful! Look 1 is my favourite
WOW i love this post. if more women dressed like this in my town I wouldnt be single lol
All I can say is WOW. This lovely lady kills in with every look!
Too bad down here in Texas, women do not take such risks.
I’m loving how you incorporate Women into your posts from time to time. Even though most of the clothes do not pertain to Men, we can still see how colour and pattern really make an outfit pop. Helen, you are gorgeous!
Kool designs
OMG Dan!I love it!
So manly but at the same time so sexy!
I love the bow-tie , the hat , the tie and…the lady!
;-)
You’re the the best!
Thank you!
Emanuel Iuhas
Visual Merchandiser/Fashion blogger
http://www.modasicevamaimult.blogspot.com
this is so awesome ! that girl looks so good… damn!
All I can say is …”Duh, Winning” Helen killed it on all accounts. As a man, I can definitely appreciate a woman who can wear man’s clothing and still look extremely sexy.
Looks #4,5,6, AND 7 is what I’m talking about. It’s a shame that here in TN woman wouldn’t even think of such creativity. Perhaps I should suggest this blog to some of my girl-friends….Either way, great post.
P.S. Dan, what venues do you hit up to meet such beautiful well-dressed women?
Awesome stuff. This young lady is so elegant and classy. The looks are pulled off with such ease. Nothing is forced. Helen looks beautiful and very much like poppy Montgomery from “without a trace” good job SB team.
Love the flannel shirt in look #6 paired with a hot skirt… you kind of forget she’s wearing a flannel shirt
I love the school prep look! So cute…
jen
http://blankwhiteframes.blogspot.com
Awesome post! I’d love to see my wife in any of these great looks!
That woman has amazing style, and she is gorgeous! She pulled off all of those looks perfectly. I think it’s really cool that she wore a lot of pieces that were relatively inexpensive–pieces from Express, Urban Outfitters, Forever 21, and even Foxhead! More women need to dress like this.
Loved every single look. Great post
dapper dan,
your female readers should be envious of miss weselcouch twofold. impeccable style and a classic beauty. great work
shades of the 1980′s! but different. interesting.
Finally something relevant for me! Thanks for doing this.
Fantastic post. Helen looks gorgeous. Cheers.
This is a post I’ve been waiting for… so glad to see all-season women’s styles feature on SB — this is perfect!!! Thank you, thank you! She pulls off the menswear look while looking perfectly feminine, which can be a real challenge. KUDOS to everyone involved with this post.
This girl pulls off these looks with ease
Wow Incredible!
Hot
OMG this girl is SO CUTE!!!!
http://theperiodblog.blogspot.com
Wow! I live in NYC, and I’d be blown away if this girl walked by me with any of those numbers on…
Who IS this babe?!
HOT!
More seriously, there is something about women with traditional neckwear that makes men (and me) melt. I’m amazed that women everywhere don’t use this to their advantage.
Great outfits!