For style, Timberlake looked to icons for inspiration: Johnny Cash, early Elvis, Sinatra, Dean Martin. “It was more about a certain swagger than the actual clothing,” he says. His stepfather, Paul Harless, taught him respect for the ritual of dressing. Harless would lay out his suit before bed, matching loafers to belt, choosing socks that went with his tie. “It wasn’t always about color coordination—it was what he envisioned to be the full picture,” says Timberlake.
JT’s Style Tips
Make “you” shine through
Timberlake finds that he receives more compliments when he adds an unexpected item, like a favorite hat, dog-tag chains, or beat-up black military boots. “The more ‘made-over’ you are, the more ridiculous you start to look,” he says. “You become distanced from who you are because it looks so contrived.”
Start at the bottom
Timberlake inherited his stepdad’s attention to detail. “I used to keep my Air Jordans icy white,” he recalls. “I had one toothbrush for my teeth—and a couple of toothbrushes for my shoes.” Don’t underestimate the power of well-tended accessories. Keep a tin of neutral shoe polish or mink oil in your desk drawer so you can buff up your kicks before meetings or dinners.
Tailor your look
Timberlake’s stepfather had his clothes tailored to suit his short stature—and to reflect his attitude. “He had his pants hemmed slightly longer in the front,” Timberlake recalls. “They kind of fell in toward his heels and it looked really cool when he walked.” Shorter men should make sure their trousers are tailored to break right above the shoes. This creates a smooth, elongated line.
When you’re choosing a fragrance, Timberlake suggests just a spray or two of “something that brings out your own scent—you shouldn’t just smell like a product.” He prefers lighter, citrus scents, but fair complexions like his tend to be drier, and dry skin doesn’t retain subtle aromas as long as other skin types do. The scent he developed with Givenchy, Play, balances a citrus scent with powerful notes of amyris wood and patchouli, so fading is minimal.
Don’t date yourself
The clothes used in the Samberg-Timberlake digital shorts are half the fun. “You can look at those outfits and pinpoint the exact chronology of the pieces because those were the things that were popular,” he says. Go ahead and embrace trends, but mix in at least one classic element—straight-leg jeans, say, or a solid oxford-cloth shirt—to avoid a laughable stereotype.
Read more about Justin’s style at Men’s Health