A Woman’s Perspective feat. Style Girlfriend

February 13th, 2013

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After four years of experience writing about style and answering questions from men all over the world, I’ve come to find that there are several reasons why guys want to look their best. For increased confidence or performance, to be taken seriously at work or with their peers, to positively represent their families or beliefs, etc.

Let’s be real, though. At the end of the day, most of us are just trying to put ourselves in the best position to impress the ladies.

So what better way to provide that advice than to reach out to an attractive woman and get her opinions on men’s style. For this, we teamed up with Megan Collins, the witty blogger behind Style Girlfriend.


Style Girlfriend is all about men’s style from a female perspective. My goal is to give guys the inside track on what women want to see them wearing…and what we definitely don’t.

Women appreciate when a guy takes care with his appearance. And little things make a huge difference. Tuck your shirt in to your pants. Wear a tie. Swap out your usual sneakers for a dress shoe or a boot. You don’t have to leave the house in a three-piece suit every day, but women can tell when you’ve made an effort. It doesn’t go unnoticed, even if we don’t explicitly compliment you on your outfit.

I’ve always taken the approach of calling myself a fan, not an expert. I know what, as a woman, I like to see a guy wearing, so I just focus on that.”

We invited Megan to our studio and gave her simple instructions: using anything from the TSB styling closet, put together three looks (one casual, one business casual, one corporate) that you consider to be the most attractive on a man.

Here’s what she came up with.


1. Weekend Casual


In your opinion, what looks most attractive on a man in a casual weekend setting?

When he looks like he didn’t sleep in his clothes! Even though it’s the weekend, guys should still think about what they’re wearing. There’s casual, and then there’s…wearing pajama pants to go pick up the paper and grab a coffee. Don’t be the guy in pajama pants.

Jordans, eh? Are they sexy? Is it because they’re official Jordans, or just cool looking sneaks?

My love affair with Nike goes way, way back. My sister got me into AirMax 95s when I was in middle school. I still have a few colorways sitting in my closet, where I admire them lovingly from time to time. They’re not really my style anymore – if I wore sneakers now, I think I’d look like Justin Bieber. Beyond that, I have dated a few sneakerheads in my day, so I probably harbor a thing for fellas sporting a beautiful shoe.

Where do guys go wrong with casual outfits? Turn-offs? What’s trying too hard/not hard enough? 

Too casual! I totally get that you want to be comfortable, but you can be comfortable and stylish at the same time. I think too many guys assume if they’re going casual, it gives them a pass not to still look put-together.

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  • jim

    The point of this post is lost in the first suggestion. This isn’t about what “women” want to see men wearing, it’s about one specific women would like to see guys wearing.
    How many women grew up loving sneakers and dating sneakerheads? I’m guessing most women would never prefer a guy to wear flashy basketball sneakers. And the denim jacket under a sportcoat would only be suggested by somebody in the fashion industry.
    My intention is not to knock her opinion, it’s just to point out that it’s one specific woman’s opinion.
    If you want to dress well for most women (that aren’t really into fashion), just adopt the j crew look. You’ll never stand out (whether good or bad) but you’ll always be dressed well.

  • Alvin

    Not sure I totally agree with the whole composition of this look.

    Seems like too many “High School College” clichés at the same time for me.
    Maybe if the look was toned down with a different style or colour of pumps.

    Also bit of a colour clash going on.

  • Rory

    Love her website. She knows her stuff.

    She’s also bloody gorgeous. Has to be said.

  • Cory

    Would she like a style boyfriend? Great post, dudes.

  • Mattew Donato

    The Jordans!

  • Joe

    Nice post idea. So – sneakers, a backpack and a letterman? I suppose if the lady insists… (Maybe this is Glee’s effect on our culture).

    • http://tsbmen.com Dan Trepanier

      Thanks Joe.

      But Jordans, a backpack and a varsity jacket makes you think of Glee?

      • Joe

        LOL – aren’t sneakers, lettermans, and backpacks the Glee uniform? Actually it does make me think high school, perhaps a more style conscious and on-trend high school look, but still high school.

        I do though like the idea of a post with a woman’s touch, even if I’m not crazy about every look. Good luck at homecoming ;)

  • Kiel

    Crimeny, what an adorable woman.

    I feel very relieved by this post. I thought it was gonna make me all insecure, but it turns out I generally have the basics in check. I am THRILLED that she included sneakers in the casual look. I think they are sorely maligned. I am into retro-sporty looks (track jackets, sweat bands) that are informed by menswear standards. I get many compliments on my grey and red Rod Lavers.

  • Vic

    You guys just keep steeping it up! I can’t believe it.

  • Pat

    Great article. One part that I think would add value however is a a section for night out on the town / club. But it is the same principles either way.

  • LouCaves

    A second opinion is usually a good thing if it’s constructive (not just a simple thumbs-up or down). Fortunately, I get that from my girl.

    Confidence, fit and the way it’s pieced with everything else is important. I can’t pull off cuffed/rolled up jeans but TSB and other cats I see own that look.

    Stick with you gut.

  • Chris

    “if you feel great in it, you’ll probably look great too…” – truer words have never been spoken…After inquiring about this perspective, I was hopeful it would generate a post…you guys continuously exceed expectations; great work as always…

    • Anonymous

      Oh…and Megan – WE ARE…

  • James

    Not a bad idea, but if you are well groomed and have decent clothes its all just based on the girls taste in what she likes. Just like men, women will be attracted to certain types, so it would be hard to try and dress to please the opposite sex.

    As Mystery said about female attraction “What a girl says and what she responds to are two different things”

    • scott

      So rad to quote Mystery

  • Bob

    Very creative idea for an article.

    I will admit though that it’s no small task asking a lady to dress you guys when you guys already do it so damn well. Relying on female opinion has personally afforded me diminishing returns on everything except fit, as I slowly climb the style ladder.

    Perhaps another approach to capturing the same perspective would be to have her assess what she likes/dislikes on the #WIWT.

  • Kevin

    My two favorite style blogs coming together? This just made my day! I hope you collaborate more in the future, since it’s always nice to get an outside perspective every now and then.

  • Joe

    Gotta love that Megan! Knows what kinds of looks a guy should go for; not to mention, it doesn’t hurt that she’s pretty, too.

  • Sergio

    I just can’t get with Look #2. I think the herringbone blazer by itself or the denim jacket by itself would have been more than enough and more visually appealing. That or the unbuttoned blazer just isn’t flattering to the look.

  • Don

    the denim ruins it a little for me personally… I think go either the denim or sportscoat. also, wearing both is not practical as it will almost always be too hot in most indoor places.

    great post though :)

  • http://www.thekacar.com Mustafa K

    Getting the females perspective is key. Great read from a different angle.

  • Jerome

    Amazing post as usual.

  • John

    Love the second look, although my herringbone jacket might be too tight over a denim jacket (similar to your tweed jacket over holiday sweater on a previous post).

    You should have included more pictures of Megan though!

    • http://www.tsbmen.com Westley Dimagiba

      we don’t want you guys to get too distracted now hah