Have you seen this guy in recent years? Most likely you have, because he’s everywhere: awards shows, red carpets, SNL, movies, even your local Target. Quite impressive, considering he was once part of a teen boy band destined to forever linger in the memories of girls who attended high school in the late 90s and early 2000s. It seems that if you’re part of a boy band during that era, there’s no elevating above that, at least not in the public eye.

Timberlake has proven to be a showman, an entertainer, a man of many talents a la Diddy. Hate ’em or love ’em, these types of guys seem to be unstoppable forces whose talents transcend their initial personas they used to put themselves in the public eye.

Whyyy JT. Why.

Regarding matters of style, Timberlake wasn’t always in top form. I mean, look at the picture above. Eesh. Chain wallets? Oversized blazers? Baggy bootcut denim with flip flops? Holy shit.

You know what though, I forgive him. He experimented with trends when he was younger (something I’m also guilty of doing) but he probably realized the importance of maturing his own style as he grew up.

I mean, look at the guy now:

Muuuch better. Phew.

Timberlake understands the proper cuts and fits (slim, but not snug). Keep things simple with dark jeans, a crisp white dress shirt, and a thin, understated pin dot tie. You could wear this combo five days a week and always look fresh.

Same with your outerwear. Updated trenches hit mid-thigh, or the tip of your middle finger when your arms are at your side, hands flat. Shy away from those floor-length numbers, they’re often HUGE and billowy and unnecessary. I’ve yet to see someone pull that off or make it look good (unless you’re in The Matrix). Leather jackets shouldn’t hang like a tent off your body, it should fit like you ride a motorcycle and you’re avoiding wind resistance.

Pay attention to the way the sleeves fit on both jackets. They’re trim and lack any excess fabric. They end at the wrist bone, leaving enough room for the shirt cuff to show off. You want that. Follow it. All your jackets should fit this way (even your sport coats,) and if they don’t, print out this picture, head on over to your local tailor, and let him know you want Justin’s sleeve length.

Dressing well doesn’t have to mean stuffy suits and stuffy ties. Modernize your look, thin down your tie and your sleeves, choose slimmer clothes when you’re out shopping. Fit and proportion are everything and can make or break your look; just check out the before and after of Mr. JT himself.

I don’t care so much if you hate or love JT, or if you think his stylist dressed him. It’s irrelevant. What I do want to know is, what are your thoughts about fit, proportion, and the importance of both? Agree? Disagree? Let me know in the comments.

As always, thanks for reading. I’d love if you subscribed to Effortless Gent by email or RSS. You should also follow me on Twitter while you’re at it. :] Lastly, don’t forget to enter to win a tie or bow courtesy of Lumina Clothing! Check out the post right here.

photo credit People Magazine, GQ

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