Guys with these kinds of weak, floppy follicles do best with either very short or very long hair; anything in between is almost guaranteed to look like a bowl cut. That's fine if you're six, but it's less than ideal if you're trying to hold down – or get – a job.
To avoid resembling your middle school yearbook photo, ask your barber to layer your hair. Layering is the practice of cutting hair so that it falls at various lengths and doesn't create hard lines. For the genetically floppy, this means looking more wind-blown and less tousled.
Vaughn also recommends talking product if you're combating lifeless locks. To give a jolt of life to the style, consider a molding paste with microfibers. It's light enough to keep your hair from falling flat but allows you to do a bit of sculpting. [Vaughn Molding Paste, $26 for 1.7 oz; v76.com]