10 Comments.

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

PUBLISHED January 30, 2011


Barron is the Founding Editor of Effortless Gent and the Cladright Association. He's from San Francisco but currently living in New York. Connect with him on Twitter, Facebook, Instagram, or Tumblr.



  • Red_warrior47

    I agree that fit is one of the most important factors in clothing, but I do disagree with your thoughts on the modern trench coat….sorta.

    IMO, a trench as you describe is just fine, if you don’t plan on wearing a jacket underneath (basically wearing the trench *as* a jacket, as in the photos. But as outerwear *over* a suit, I believe the sleeves should be a bit more generous. Not billowy, but roomy enough to not wrinkle your suit. I also feel that outerwear should protect what’s beneath it. If my shirt sleeve is showing during a storm, they’re going to be sopping wet by the time I’m inside somewhere!

    • http://effortlessgent.com Barron

      You’re right, as outerwear, there will be more room in the sleeves and body to accommodate the suit jacket. The problem with most men, though, is that they think they need to buy 2 sizes bigger than their actual size. This is where the billowiness (is that a word?) and bagginess (how about this?) comes into play. Someone needs to tell these guys that you don’t need to go up in size when you buy a trench; you buy your true size, because the coat maker designed it accordingly (meaning he knew you were gonna have a suit jacket under there.)

      Thanks for your clarification.

  • http://www.whatshouldmenwear.com What Should Men Wear

    Wearing the right cut and fit is important about clothing, but you always have to feel comfortable in whatever you’re wearing. So finding the best style exactly for you, your own personal style, is probably even more important that fashion, mixing or fitting.

    • http://effortlessgent.com Barron

      Definitely, and that’s something I’ve always stressed here. It’s all about finding the best style for you, that cross between what you feel most comfortable in and what looks best.

  • http://twitter.com/lesb3 Lester Bryant III

    He was pretty sharp at the SAG Awards last night too: http://socialitelife.com/justin_timberlake_2010_sag_awards-01-2010

    • http://effortlessgent.com Barron

      Nice! I missed the awards show. I’m surprised at the shirt color choice; never would’ve considered that. Dig the bow. Thanks for sharing Les!

  • Dan

    If I may ask what might be a dumb question, what do you think the “good” clothes on the right would be appropriate for? Like, what situation? Sometimes I wonder what fashion editors think we’re dressing for and think we all have photo shoots where anything like that would be appropriate.

    • http://effortlessgent.com Barron

      Not a dumb question at all. The leather jacket and vest picture? I don’t find that too outlandish, do you? I wear a variation of that same outfit all the time, albeit not as snug since I’m not as trim as JT. I also work in a casual office where I see people wear shorts and flip flops when the sun shines. Eesh.

      Guess it depends on where you’re from, what industry you work in, and what you’re comfortable with wearing. Even if you chose to leave out either the vest or the jacket, that would still be a pretty decent outfit that one can wear pretty much anywhere (shirt tie jeans jacket, or shirt tie jeans vest).

      • Dan

        You might be right; part of it is that I come from Wisconsin, which helps explain half of it. I also don’t work in a traditional office setting, which might account for the other half. So when I see pictures like that I’m usually thinking “wait, when can I wear something like this….EVER?”

  • Austin

    Hi- any ideas were I can find a good quality tench coat that won’t break the bank?