01of 12Teen HeartthrobsFred Duval/FilmMagicWho can resist these wholesome smiles?02of 12FutureSex/RhinestonedSteve Grayson/GettyThe tips of Justin’s gloves disappeared in 2000.03of 12Denim DaysLisa Rose/JPIThe star went all-demin with then-girlfriendBritney Spearsin 2001, and we still talk about this iconic fashion moment two decades later.04of 12Bleach BumMiranda Shen/Celebrity PhotoWe’ll chalk up the buttered-noodle hair and chain wallet to the fact that this pic is from 1998.05of 12Velvet CrushRichard Young/Rex USAJT went full force with the velvet tracksuit trend in 2003.06of 12Corn-y RowsTrapper Frank/CorbisIn 2000, JT rocked cornrows with a navy blue bandana.07of 12Mini MeMitchell Gerber/CorbisEven Justin’sNo Strings Attacheddoll rocked his overgrown curls in 2000.08of 12Space CowboyAndre Csillag/Rex USAHopefully there’s a new outfit in that package … is what we think he’s thinking in this vintage pic from 1997.09of 12Sherlock HomiesSGranitz/WireimageNow we know what caused the Great Corduroy Shortage of 2001.10of 12LL Cool JTRon Wolfson/GettyHe’s wet. He’s in a bucket hat. And this photo is from 1998. We know what you did last summer.11of 12Fashion Faux PasGilbert Flores/Celebrity PhotoThe pants say, “Wasssap” (hey, it’s 2000). And the turtleneck says, “This photo is old.“12of 12Bandana BanditJustin Timberlake (center) and Joey Fatone (left) in 2000.Chris Hondros/NewsmakersYoung JT clearly loved his bandanas. It seems as though he had a collection of several in different shades of blue.
01of 12Teen HeartthrobsFred Duval/FilmMagicWho can resist these wholesome smiles?
01of 12
Teen Heartthrobs
Fred Duval/FilmMagic

Who can resist these wholesome smiles?
02of 12FutureSex/RhinestonedSteve Grayson/GettyThe tips of Justin’s gloves disappeared in 2000.
02of 12
FutureSex/Rhinestoned
Steve Grayson/Getty

The tips of Justin’s gloves disappeared in 2000.
03of 12Denim DaysLisa Rose/JPIThe star went all-demin with then-girlfriendBritney Spearsin 2001, and we still talk about this iconic fashion moment two decades later.
03of 12
Denim Days
Lisa Rose/JPI

The star went all-demin with then-girlfriendBritney Spearsin 2001, and we still talk about this iconic fashion moment two decades later.
04of 12Bleach BumMiranda Shen/Celebrity PhotoWe’ll chalk up the buttered-noodle hair and chain wallet to the fact that this pic is from 1998.
04of 12
Bleach Bum
Miranda Shen/Celebrity Photo

We’ll chalk up the buttered-noodle hair and chain wallet to the fact that this pic is from 1998.
05of 12Velvet CrushRichard Young/Rex USAJT went full force with the velvet tracksuit trend in 2003.
05of 12
Velvet Crush
Richard Young/Rex USA

JT went full force with the velvet tracksuit trend in 2003.
06of 12Corn-y RowsTrapper Frank/CorbisIn 2000, JT rocked cornrows with a navy blue bandana.
06of 12
Corn-y Rows
Trapper Frank/Corbis

In 2000, JT rocked cornrows with a navy blue bandana.
07of 12Mini MeMitchell Gerber/CorbisEven Justin’sNo Strings Attacheddoll rocked his overgrown curls in 2000.
07of 12
Mini Me
Mitchell Gerber/Corbis

Even Justin’sNo Strings Attacheddoll rocked his overgrown curls in 2000.
08of 12Space CowboyAndre Csillag/Rex USAHopefully there’s a new outfit in that package … is what we think he’s thinking in this vintage pic from 1997.
08of 12
Space Cowboy
Andre Csillag/Rex USA

Hopefully there’s a new outfit in that package … is what we think he’s thinking in this vintage pic from 1997.
09of 12Sherlock HomiesSGranitz/WireimageNow we know what caused the Great Corduroy Shortage of 2001.
09of 12
Sherlock Homies
SGranitz/Wireimage

Now we know what caused the Great Corduroy Shortage of 2001.
10of 12LL Cool JTRon Wolfson/GettyHe’s wet. He’s in a bucket hat. And this photo is from 1998. We know what you did last summer.
10of 12
LL Cool JT
Ron Wolfson/Getty

He’s wet. He’s in a bucket hat. And this photo is from 1998. We know what you did last summer.
11of 12Fashion Faux PasGilbert Flores/Celebrity PhotoThe pants say, “Wasssap” (hey, it’s 2000). And the turtleneck says, “This photo is old.”
11of 12
Fashion Faux Pas
Gilbert Flores/Celebrity Photo

The pants say, “Wasssap” (hey, it’s 2000). And the turtleneck says, “This photo is old.”
12of 12Bandana BanditJustin Timberlake (center) and Joey Fatone (left) in 2000.Chris Hondros/NewsmakersYoung JT clearly loved his bandanas. It seems as though he had a collection of several in different shades of blue.
12of 12
Bandana Bandit
Justin Timberlake (center) and Joey Fatone (left) in 2000.Chris Hondros/Newsmakers

Young JT clearly loved his bandanas. It seems as though he had a collection of several in different shades of blue.
source: people.com