Rule #1 of the TSB Office: Bring Your “A” Game.
Comment below to let us know which outfit is your favorite!
Wes
“Tried to find some inspiration from our coffee table book and ended up taking the book with me to white backdrop ”
Dan
“When you run a start-up, you can wear sweatpants to work. That doesn’t mean you should dress sloppy. #TailoredSweats.”
Towni
“Went with classic prep layering today. Easy to swap layers and stay comfortable in this shifting NYC weather.”
Alex
“Freaks & Geeks y’all”
Angel Ramos
“Who says you can’t wear white jeans in the winter?”
Angel stopped by the studio so we invited him to appear in today’s WIWT. Check out his feature here.
Thanks for reading,
The TSB Team
Photography by Alex Crawford.
Check out more of his work at alexcrawfordphotography.com.






84 Comments Add a comment
towni
Towni!
Alex deserves way more than props than he’s been getting. Love the camo pants dude, where’s the jacket from?
Wes! Wes is always my favorite.
Towni !!!!!!
TOWNI TOWNI TOWNI
Id go for Wes and Town again.
Towni. Loving the dub monks!
Angel for rocking the white like a baws!
Angel ftw. Wes and Towni close second.
Ain’t diggin the not-quite-tailored-perfectly sweats tho. Sorry Dan.
Hey TSB Crew!!
I’m going to give it to Angel & Towni for 2nd!
Best,
Sabir
I think that Alex, Wes, Townsend, and Angel look great! Well, done on the conspicuous lack of high waters Wes ;-). And Townsend, good for you for continuing to buck the Internet menswear trend of raw denim and high waters! Angel, a little tight pants, but what the Hell, why not?
Now Dan, we need to talk seriously. I’m afraid this style thing has gone to your head. It’s okay. Sometimes we don’t know where the boundaries are until we’ve crossed them. But friend, you are several states over the line and charging at full steam. Tailored, cuffed, sweatpants with all other items being at least business casual?! As my wife said, “It looks like he spilled something on or peed his pants and had to put on whatever was around. If he were my office, I’d send him home to change.” Obviously, we like the site and I have stolen several of your earlier outfits for myself, but you are getting increasingly more bizarre and now it’s a joke. Come back, sir. We miss you.
Luckily for all of us, John, I don’t work for your wife, or in an office. I started this business so that I could wear whatever I wanted and inspire men to think outside the box ;)
Thx for reading.
Owned.
The term is technically called pants with a slight break or cropped if you’d like.. Calling them high waters signifies that you’re quite out of touch with menswear in general. Also, if you were to wear raw denim for about a year or two it would look exactly like the one’s Towni’s wearing. Unnecessary insulting posts like yours make me shake my head. Especially insulting a man’s style when he’s already renowned for being one of the best dressed men in the U.S. Uncalled for man.
John…10 dollars says you didn’t guess those were sweats until you read the description.
Let the guy say they look like shit if he thinks so. Buncha cheerleaders.
Towni!
Angel!
Wes with the solid layering.
My first vote for Wes!
Wes, I’m lovin the boots!
Wes by a hair over Towni.
Wes! Combining rugged with your essential well-put-togetherness was a great choice. You get my vote.
thanks Affresco!
Wes.
DT. Coming full circle photographing the original TSB sweats+cadigan+navy blazer outfit again;)
haha. Almost went with the same cardigan too.
Great memory TO
i see deron williams joined the tsbmen entourage
Wes.
Really like that jacket Wes, but this one has to go to Towni.
Wes!
Angel, by a long shot, but for the purposes of the competition I’d go with:
1. Towni
2. Wes
3. Dan
4. Alex
Angel! for facing the cold weather with simplicity
but for the sake of the tally, my vote goes to wes
Angel, you killed it bro. I’m gonna wear my white jeans tomorrow.
Angel is style-pornography. On any other day Townsend would be a winner, but here nobody else has a chance.
Even though his duds look seasonally questionable, Angel still wins this one hands down.
What’s with the untied boot laces? Looks naff in front of a white sheet, and more than likely impractical walking on the street.
Towni, though Angel would have gotten my vote with another shirt button undone.
Good point. Opening one button is a strategy with very limited applications.
Dan!
Wes. For sure. But Townis monks #1
Angel wins by a mile! Not that the rest of you don’t look amazing, because you do. It’s just that Angel kills it with such a simple look.
I have to go with Towni, the jacket, the belt and the (tucked in) rugby, just couldn’t add up better
Towni hands down, perfect New England style
the guest drops in and kills it!
Townsend because of the tie.
Angel.
1) Towni
2) Angel
3) Wes
4) Dan (not a fan of the sweats)
5) Alex
Angel for sure, even if he’s just swinging by!
Towni. I like the rugby-over-shirt-and-tie look.
Also I am totally wearing white jeans today. It was a good decision.
wes
Townsend.
But Alex gets props for liking Freaks and Geeks!
Townsend.
I like the colours and the D-ring belt.
I think Towni has this one, though everyone was pretty solid today.
Angel for sure! All look dope but i’m a bit bias!
Wes
Dan’s got this one…i think more people should hop on the tailored sweats game…I’ve tailored a few pair for myself and love them. And, you can’t judge them if you haven’t tried them.
Give them a go!
I like the slim cut tailored sweats look, as well. My vote is Dan.
Does anyone have any recommendations for sweats brands that are slim cut and tapered near the ankle?
Dan…killin’it with the sweats on.
This is tough. Wes is the clear winner, but 2nd place is an even tie between Alex and Townsend.
Wes, camp collar, flannel collar, shawl collar, peacoat collar?!! Damn!And those boots are really cool. The outfit reminds me of some kind of french street-tough. Like you’d try to sell me a bicycle or something.
Alex, the bulkier jacket is really complementary to your build. You look tough. Pants fit perfect. I like that you wear things that could conceivably be pulled off outside of the big city.
Angel for today. Townsend in a close second digging the layers!
Wes gets the cash!
BTW: Dan’s living a double life: Blogger by day…PHX Suns Point Guard by night. He is…….Goran Dragic! Check out the link below (scroll down to pic # 3). And, don’t let that new ‘fake’ beard fool ya! :) You’ll be able to clearly discern that in fact he IS running the Point out in the Valley of the Sun….Dan’s visibly angry with Micheal Andrews in the pic, too. Caption: “There’s only 3 suits here?!….I clearly ordered 4 new ones if you RECALL, MIKE!!!! WTF!!!!” (Pic #3)…..lol.
http://sports.yahoo.com/blogs/nba-ball-dont-lie/ball-don-t-lie-2012-13-nba-season-215634707–nba.html
hahahah! Dan is Steve Nash’s protege? Go figure.
Hahaha. My hoops career is long behind me. But that’s not to say I can’t still get buckets!!
Angel FTMFW! It was so warm in Bmore yesterday I rocked the white jeans as well.
Great jacket on Towni.
Details?
Towni. Digging the rugby, man.
Wes got the W today
Alex
Wes
Towni. Feeling that New England look!
Angel, the WIWT guest is looking too fresh.
Towni. Lovin’ the color palette!
Angel is a super close 2nd though. A tie or scarf would have clinched my vote for ya!
Angel. Dan’s top half would have won, but I can’t buy into sweat pants and shoes right now
Angel.
There’s something mildly unsettling about Dan’s sweatpants, though.
that’s the point :)
Wes, of course!
Angel
Towni – the OCBD/knit(?) tie/rugby/tweed jacket layering is a go-to. Angel a very close second, though.
Angel. Lol
Everyone’s looking good, but Faceman is on a roll!
Im stuck in a tie between wes and angel’s outfits. Both were on point today. http://averagemanfitnessandstyle.blogspot.ca/