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Personal Style Upgrade: Andre Milton

March 11th, 2013

Dre and Westley have been best friends since elementary school.

After seeing Gabe’s transformation in our first Articles of Style Upgrade, Dre’s girlfriend Samantha suggested that he be the subject of our next makeover.

Being gentleman and all, we couldn’t turn down the young lady’s offer.

Check it out!

    1. Just Chillin’ – Before


    Dre is an ex-football player (6′ 235 lbs) with a friendly, laid-back disposition. Since his days on the gridiron he’s always gravitated toward casual, loose-fitting clothes with “lots of personality”.

    We thought he could benefit from simplifying his look a little, allowing his charming personality to shine through.

    What we can learn from Dre’s “before” look:

    • A broad guy in a bold graphic tee can look overwhelming. A busy pattern, like this one, widens out his frame and distracts the eye.
    • A leather jacket should be simple in design and, more importantly, made from genuine leather. You can find full-grain vintage pieces, like the one below, for roughly the same price as those over-designed “pleather” numbers you find in stores like Urban Outfitters or Express.
    • A henley offers more elongation at the neckline than a crewneck tee. It’s a very subtle slimming effect that also conveys confidence.
    • Baggy jeans offer no shape or silhouette, making a broad guy look heavy (and sloppy).
    • A subtle “front tuck” not only shows off the belt, but breaks up the torso and legs. This gives his body a more balanced proportion and gives him the illusion of longer, slimmer legs.
    • Save the patent leather gym shoes for the gym. The weekend calls for a classic sneaker or a simple desert boot.

    Just Chillin’ – After


    • Brown leather jacket Vintage
    • Grey henley by JCrew
    • Brown Winton woven braided leather belt by Trafalgar
    • Washed denim by Levis
    • Beeswax desert boots by Clarks

    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

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    • 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

    3. Job Interview – Before


    In fairness to Dre, he doesn’t often wear a suit. Regardless of your lifestyle, though, sometimes you have to look professional.

    What we can learn from Dre’s “before” look:

    • It’s either a matching suit, or a jacket and trousers that complement each other and have a noticeable level of contrast. Avoid pairing a blazer and trousers that are different shades of the same color. 
    • Looser fitting clothes do not make a broad man look slimmer. They make him look wider, and sloppier.
    • A solid red shirt is not business appropriate, or particularly flattering.
    • Black and red is also not the most approachable colorway for a necktie.
    • For a go-to suit, make it single-breasted. Keep it buttoned to keep your silhouette in check.
    • It’s a myth that larger guys shouldn’t wear patterns. Just keep them subtle, with a noticeable contrast (like a faint windowpane, tight micro-check, and wide rep stripe).
    • Adding a waistcoat is a mature touch that’s also functional – it keeps the shirt, tie, and midsection streamlined (especially with the jacket open).
    • Patent leather shoes are not the best option for business, especially after they’re worn-in and hard-creased.

    Job Interview – After

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    • Grey subtle check 3-piece suit
    • Purple micro-check shirt by Charles Tyrwhitt
    • Navy stripe tie by Brooks Brothers
    • White cotton pocket square
    • Captoe lace-ups by Johnston & Murphy
    • Leather folio by Holdall&Co


    Thanks for reading, and special thanks to Dre for participating.

    Yours in style,

    Dan Trepanier


    Styling by Dan Trepanier. Photography by Alex Crawford

    • jarad F

      The upgrade to his collection definitely matured his look. Very mature look in all 3 styles.

    • http://undefined Jason P

      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.

      • http://undefined Jason P

        For the record, I’m the same build as Dre as well.

    • http://undefined undefined

      Great make over he should consider cutting the hair.

    • http://www.foreverkirk.com Forever Krk

      Now thats a make over . I really like the happy hour makeover.

    • Paul

      Great “makeover”, and good tips for the bigger guy!

    • Deacon021

      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

    • Sidney

      Out of curiosity, who picked the clothing for the after looks? Dre or the TSB team?

      • http://tsbmen.com Dan Trepanier

        I did, with input from Wes and Dre.

    • Pete Serrano

      HELL of a job guys. You did great. Love this site.

    • TO

      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:)

    • Cory

      What Johnston & Murphy shoes are those? I can’t seem to find them anywhere.

      • http://tsbmen.com Dan Trepanier

        You can find a link to the exact pair in the “Shop This Look” section – see the right column.

    • Felix

      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.

      • http://tsbmen.com Dan Trepanier

        Thanks for sharing your opinions Felix. Appreciate your support.

      • TO

        @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

    • Jaime B

      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!

      • Sosa

        probably pinned for the sake of the shoot

      • http://tsbmen.com Dan Trepanier

        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.


    • Khalid

      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. :)

      • http://tsbmen.com Dan Trepanier

        Well said!

    • Adam

      It’s always amazing to me what just a little more care can do. Great post.

    • M-O

      Outfit #3 would make The Bunk real proud. Amazing job as usual!

    • Alex

      Well done, Dre. Lookin’ sharp!

    • http://undefined Brad

      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!

      • Rob A

        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?

        • http://tsbmen.com Dan Trepanier

          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).


          • TO

            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.

        • Khalid

          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.)

      • Anonymous

        I have a similar build and had some luck with Eddie Bauer.

      • goofgnar

        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.

        • Quark

          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).

      • Rob A

        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…

    • Rory

      It is amazing how a few little changes can transform a person. He looks sharp as hell now.

    • Derric

      He legitimately looks nearly 50 lbs lighter in the 1st and 3rd sets. Plus, that is a great shirt in 3rd for only $70.

    • John

      Awesome leather jacket on look #1.
      He really looks better (and slimmer) in slim(mer)-fitting pants!

      Keep the upgrades coming!

    • Bob

      Nice looks! I really like the Just Chillin’ – After look. However, this particular jacket appears to be large in the shoulders.

    • http://greenspree.ca Andy Collier

      The third look is the best transformation in this post by far! He looks like he lost 30lbs!