Menswear Dog: Suitsupply, $569
Next Level: J. Crew, $675
You Only Live Luxe: Paul Smith, $1,505; Trousers, $615 (Total: $2,120)

It isn't enough to have one suit, you need one to stunt in. The #menswear dude wears suits not because he has to, but because he wants to. So it better fit perfectly. You can break apart the jacket and the pants and wear them separately for more mileage. Rock the jacket with denim and chinos, or pair the pants with a leather jacket or military-inspired outerwear like M-65s.