3. Suited Up
In your opinion, what looks most attractive on a man when it comes to getting suited up?
When his suit actually fits him! It’s funny, when I was younger, I thought I didn’t like a suited-up look. It turned out, though, that I just hadn’t seen a guy wear a suit well. That’s because the only examples I had to go on were guys – well, boys really – in suits at prom, or graduation, or their first job interviews and all those suits were terrible. And I mean, ter-r-r-r-r-i-b-l-e. The suits themselves were boxy, the shirts were puffy, the ties were…actually, let’s not even get into the ties. The shoes were – almost without exception – square-toed. Once I was around guys who really knew how suits were supposed to look…oh. My. God. I was a total convert.
Love that you kept it classic with a two-button suit in a solid dark color. How do you feel about DB suits? 3-piece? Bolder colors/patterns?
I think if a guy is new to wearing suits (or perhaps more accurately, wearing suits well), he should start with the basics. Invest in a dark gray or navy two-button suit with notch lapels and go from there. Suiting definitely has an advanced degree of difficulty as you go more and more trendy. When it comes to more style-forward pieces (like double-breasted, prince of wales check, etc) – if you feel great in it, you’ll probably look great too. But if you’re a little nervous, then you might look less than confident.
Where do guys go wrong with suits? Turn-offs? What’s trying too hard/not hard enough?
Suits that are too big. 100%. That’s why guys don’t like suits, because they think they look like they’re wearing their dads’ old clothes. Which…they do, if they’re not wearing a suit that fits them. Throw on a jacket that hugs your shoulders and pants that end with just the slightest break and you’ll look amazing.
- Frames by Warby Parker
- Charcoal suit by Michael Andrews Bespoke
- Purple micro-stripe shirt by Thomas Pink
- White cotton pocket square
- Purple crest tie by Hickey
- Sterling Silver tie bar by Tiffany & Co.
- Brown leather wingtips by Gucci
Thanks, as always, for reading and special thanks to Megan for participating.
Yours in style,
TSBmen
Styling by Megan Collins.
Photography by Alex Crawford - alexcrawfordphotography.com.


25 Comments Add a comment
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.
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.
Love her website. She knows her stuff.
She’s also bloody gorgeous. Has to be said.
Would she like a style boyfriend? Great post, dudes.
The Jordans!
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).
Thanks Joe.
But Jordans, a backpack and a varsity jacket makes you think of Glee?
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 ;)
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.
You guys just keep steeping it up! I can’t believe it.
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.
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.
“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…
Oh…and Megan – WE ARE…
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”
So rad to quote Mystery
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.
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.
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.
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.
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 :)
Getting the females perspective is key. Great read from a different angle.
Amazing post as usual.
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!
we don’t want you guys to get too distracted now hah