Dre and Westley have been best friends since elementary school.

After seeing Gabe’s transformation in our first TSB 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