TSB Upgrade: Andre Milton

2. Happy Hour – Before

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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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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

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