2. Happy Hour – Before
Dre and Wes spend plenty of time at happy hour, and most of the time it spills into a late night out in NYC.
What we can learn from Dre’s “before” look:
- If it’s a college dive bar, a plaid shirt and runners are fine. But if you’re a grown man hoping around late-night spots in NYC, you’ll be better served in a tailored jacket and loafers (literally and figuratively).
- An untucked plaid shirt is not the most flattering shape for a broad guy, especially one where the pattern is flipped diagonally. Notice how the dark tailored jacket below really slims down Dre’s overall physique.
- Loose fitting jeans that pool around the ankle tend to look sloppy and unkept.
- Again, a deeper neckline here (this time with a v-neck instead of a crewneck) looks fresh, clean and confident.
- Dre may not be overly particular about his clothes, but he keeps his grooming on point. This is one of the best things a man can do to look approachable and confident.
- Even though he’s dressed more maturely, we kept the “after” look simple and breathable. He’s still only wearing four basic pieces.
Happy Hour – After
Featured Items:
- Grey wool/cashmere jacket by Brooks Brothers
- Burgundy cashmere v-neck sweater by Brooks Brothers
- Dark washed jeans by Gap
- Black penny loafers by Johnston & Murphy





38 Comments Add a comment
The upgrade to his collection definitely matured his look. Very mature look in all 3 styles.
THis is great! I am glad to see this because more people I know resemble Dre’s build rather than Dan (though we’re working to get there!). I am glad to see this and hope there’s more in the future.
For the record, I’m the same build as Dre as well.
Great make over he should consider cutting the hair.
Now thats a make over . I really like the happy hour makeover.
Great “makeover”, and good tips for the bigger guy!
Good to see the change and that he actually likes it which is most important.
1. Love the outfit and color choices. If the fit was a bit better it would be killer.
2. Change the v neck and give him a button down. Outside of that thumbs up
3. You guys always pull off suits really well. No lie
Out of curiosity, who picked the clothing for the after looks? Dre or the TSB team?
I did, with input from Wes and Dre.
HELL of a job guys. You did great. Love this site.
This is…wow! All these upgrades are amazing.
People have been asking for a “big man” post forever too…
I thought something was funky on the suit hems. But I didn’t put that together; smart readers!
Inspiration Dan, I might have something for you in the near future:)
What Johnston & Murphy shoes are those? I can’t seem to find them anywhere.
You can find a link to the exact pair in the “Shop This Look” section – see the right column.
Dre, great transformation!
The front tuck looks sloppy and ruins the line of the first look. Great leather piece, and good colour cohesion, just let that henley drape freely, instead of attempting the whole “i’m trying hard to look like i’m not trying look” with the half tuck. Ugh. Darker wash, no pre-distressed jeans would look even sharper.
Second set and third is great, great command of accessories.
Thanks for sharing your opinions Felix. Appreciate your support.
@Felix: I agree with the part-tuck but would add that I think he can size down one size as well! And I think the idea was the keep the jeans the same “wash” :D
Another great post TSB! Although I couldn’t help but notice the cuff of the sleeves and the hem of the pants in outfit #3. Are they just tucked back for the sake of the shoot or is the lighting leading me to conclude that some sub-par tailoring took place? Anyways, really enjoying the content you guys are putting out!
probably pinned for the sake of the shoot
Great eye Jaime! We were in a time crunch for this post, so the alterations weren’t fully completed. The sleeves and hem were pinned for this shot.
Cheers
1) Well-done styling. Still looks like the same guy, but better. Especially in that first set.
2) Future TSB contest entrants take note: Andre’s easy, good-natured smile goes a long way! It’s more than an accessory… nice clothes can’t stand in for a nice personality. :)
Well said!
It’s always amazing to me what just a little more care can do. Great post.
Outfit #3 would make The Bunk real proud. Amazing job as usual!
Well done, Dre. Lookin’ sharp!
Do you have any details on the jeans you recommended? I’m an ex-soccer player and still cycle a ton. Needless to say my rear end and legs don’t fit into most pairs of jeans. I’m thinking Dre has my same dillema.
I’d love to find something with a closer fit, but usually end up stuck with a pair of loose fit Levi’s.
Thanks, love the site!
I too have this problem. Quads, ass and hips won’t fit. When I finally do try on a pair that i’m able to get on the waist is too big.
Any suggestions?
Thanks
Find a brand/style that fits in the difficult areas (hips, thigh, seat) and have the rest tailored (waist, leg width, hem) after you’ve worn them a few times (to accommodate initial stretching).
Cheers.
Dan is right.
Fellas: old Levi’s 508s work wonderfully for me.
I Think I can claim myself in the same boat- my thighs are each 26″ or so and my “seat” (ass) is about 6″ more around than my “waist”. Found these vintage, of course.
Rob, you could add darts, as illustrated here: http://tuttofattoamano.blogspot.ca/2013/03/fitting-jeans.html
(End results seem a little TOO shapely in that photo… but done well it may solve your problem.)
I have a similar build and had some luck with Eddie Bauer.
Check out Levi’s 508s (tapered cut) – as a former soccer player and skateboarder with tree trunk thighs, these have been the best entry level jean I’ve found that can give my thighs and calfs suitable room while still being a suitable cut. If you are looking to go raw, try Naked and Famous Weird Guys – very similar fit.
You don’t find that the taper is too drastic as to appear feminine from the side/back? It definitely looks pretty feminine from the side whenever I walk past a reflection in a window/mirror, if I wear 508′s that fir my 26″ thighs, 43″ hips, and 32″ waist (Vanity size).
Thanks for all of the added comments and suggestions!
waiting for the DIY dart video subtly mentioned on the post about adding darts to shirts…
It is amazing how a few little changes can transform a person. He looks sharp as hell now.
He legitimately looks nearly 50 lbs lighter in the 1st and 3rd sets. Plus, that is a great shirt in 3rd for only $70.
Awesome leather jacket on look #1.
He really looks better (and slimmer) in slim(mer)-fitting pants!
Keep the upgrades coming!
Nice looks! I really like the Just Chillin’ – After look. However, this particular jacket appears to be large in the shoulders.
The third look is the best transformation in this post by far! He looks like he lost 30lbs!