10 Fashion Lessons We Can Learn From Justin Timberlake

JT hasn't always been the suave, but he's really come into his own.
JT hasn't always been the suave, but he's really come into his own.
Jason Merritt/Getty Images

Justine Timberlake is one entertainer who knows how to dress. He has impeccable fashion sense these days, but that wasn't always necessarily the case. He's learned quite a bit from his early dressing disasters and developed a style that manages to be individual and classic at the same time. Let's look at 10 timely fashion lessons we can learn from JT, either by his shrewd choices -- or his near misses.


Leave the Shiny Curls to the Girls

Back in his early boy band days with 'N'Sync, JT frosted his curls and came away looking more like Goldilocks than the big, sexy wolf. Extreme hair styles come and go, and once they're out, they can look equal parts hilarious and embarrassing. Consider his attempt at wearing cornrows as another example of hair flare gone wrong. If you want to look great in your prom photo after the ball is over, cultivate your daring image with something other than your hairstyle.


Coordinating Outfits Is a Bad Idea

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You've probably seen the photos of JT and Britney Spears decked out in matching denim outfits for the American Music Awards Show in 2001. It's a classic example of a fun idea that just didn't work. All that stonewashed blue looks juvenile and a bit silly today. In a recent Playboy article, JT even admitted the choice was cringe worthy. If your best gal pal thinks matching Ts or (horrors!) Christmas sweaters are a great idea, nix the notion fast and make it final.


Learn to Layer

JT is a master of layering individual clothing pieces to create a finished look. One of his older tricks involves pairing hoodies with bombers or other jacket styles. At the time, the choice was unusual but fresh and effective. It's just one example of a great layering strategy, though. Even if he's sporting a checked sweater with a crisp white shirt and snug-fitting trousers, he's learned that good dressing is about using clothes to create a finished picture.


Discover Your Inner (and Outer) Fedora

Keep those curls in check on a bad hair day!
Keep those curls in check on a bad hair day!
Kevork Djansezian/Getty Images

A hat lover from way back, JT has nailed the casual but subtly tailored look, and has a unique take on choosing the right headwear style. Instead of making the hat the main focus of his look, he integrates it with the rest of his apparel. That way, the effect doesn't shout that he spent all day in front of a mirror or simply supporting his local haberdasher. Play around with a few hat styles for fun. If you decide you like the look, there's a big upside. You'll never have another bad hair day -- one that anyone knows about, anyway.


Try Something New

Justin isn't afraid to try something new. Whether it's a double-breasted cardigan, silver suit, tweed vest or waxed denim jeans, he's always on target with clothes that fit well and offer an interesting slant on the latest men's fashions. He's not afraid to experiment and develop an individual style that's fresh but not flashy, and classic without looking old fashioned. Be brave and start looking at fashion as opportunities to express your personality.


Get Inspired

Where fashion is concerned, it never hurts to be inspired by someone who clearly knows what he (or she) is doing. Who does Justin look to for inspiration? The style icon who gets JT's creative juices flowing is none other than Kate Moss. Here's what he has to say about her: "She looks good in anything. She would look good in one of your T-shirts, in her T-shirt, in a man's suit, in a huge gown. She even makes nude look stylish...She could put a barrel on and it would be some sort of statement." What other fashion icons inspire him? He's learned lessons from the examples set by Elvis (in the early years), Frank Sinatra, Dean Martin and Johnny Cash, among others.

JT is pretty inspirational when it comes to all things sartorial, so consider watching his fashion lead and making some of his ideas your own.


Add an Unexpected Element or Accessory

Justin has a knack for creating looks that are pulled together without appearing too contrived or staged. It looks effortless, but he works at it. He's found that adding one or two unexpected touches can keep his fashion choices grounded and real. Some of his favorite quirky accessories are sneakers with suits, army boots with jeans, dog-tag chain jewelry and hats, of course.


Embrace Tailoring

JT learned early that a good tailor can be a real asset. His stepfather was somewhat short, and clever tailoring touches, like slightly lengthening his trousers in front, made him appear taller. Because he knew he looked great, he felt better about the image he presented to the world. The lesson wasn't lost on Justin: An accomplished tailor can take your style from good to great.


Use Trendy Styles Sparingly

A classic suit in an on trend color is the way to go.
A classic suit in an on trend color is the way to go.
Kevin Winter/Getty Images

Nothing dates a look like a trendy garment that's outlived its hype. To keep a look fresh, embrace classic styles like oxford shirts or straight leg jeans and coordinate them with a few trendy items, just as JT likes to do. That way, you can easily change out the latest and greatest before it becomes yesterday's cliché. You'll always have a reliable core wardrobe to work with, too. It's the safest and most practical way to look fashionably up-to-the-minute. If you're careful about your choices, you can also save money.


Wear Your Confidence

Wear your clothes instead of letting your clothes wear you. Justin has shown through the years that good dressing is really about confidence more than the appeal of any single garment or look. Own it. Your wardrobe choices are a reflection of your personality. JT likes to call it swagger: That indefinable aura that makes you appear self-assured, capable and in control. If you believe you look great, you're half way there. Have a little faith.


What Happens to Red Carpet Dresses After Celebrities Wear Them?

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Where do those red carpet dresses go after their big debuts? HowStuffWorks follows the trail.

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