Image via Complex Original
Lupe FiascoTrilly & TrulyRighteous Kung-FuStyle History of Lupe Fiasco...
Kick, Push Music Video
WHAT: "Kick, Push" Music Video
WHEN: April 2006
THE GOOD: It's good to know that everyone was a nerd at some point. Yes, he's wearing a nice varsity, but wait until you see the ones he wears next. They get so much better.
THE BAD: Those jeans. Damn. So bad that it's awesome?
Daydreamin' Music Video
WHAT: "Daydreamin'" Music Video
WHEN: July 2006
THE GOOD:
The back of this crewneck sweatshirt is so dope, we just had to choose this shot.
THE BAD: Nothing bad here. Everything from Lupe's line Trilly & Truly is awesome.
Daydreamin' On Set
WHAT: On Set "Daydreamin'" Video Shoot
WHEN: July 2006
THE GOOD: Lupe has always owned his own style—a mix of street and skate, topped with glasses on some cool nerd steez.
THE BAD: Nothing stands out, but nothing's particularly bad either.
GQ Magazine 2006 Men of the Year Dinner
WHAT: GQ Magazine 2006 Men of the Year Dinner in West Hollywood, CA
WHEN: November 2006
THE GOOD: He looks happy.
THE BAD: Patchwork leather jacket and distressed patchwork jeans...not awesome.
49th Annual Grammy Awards
WHAT: 49th Annual Grammy Awards
WHEN: February 2007
THE GOOD: That Escalade is SHININ'!
THE BAD: Ruh roh. What is this denim suit nightmare? And are those plain white grandma sneakers?
Lollapalooza 2007
WHAT: Lollapalooza 2007 in Chicago
WHEN: August 2007
THE GOOD: You can see from the style that it's definitely '07, but the unbuttoned light blue shirt and the wash of the jeans make him look summer fresh.
THE BAD: Can't hate anything about a summer music festival.
In New Zealand
WHAT: In New Zealand
WHEN: August 2007
THE GOOD: That's a sweet camo jacket by North Face. Though the military print never goes too far out of style, looks like Lupe was on the trend early.
THE BAD: Nada.
Dumb It Down Music Video
WHAT: "Dumb It Down" Music Video
WHEN: September 2007
THE GOOD: Lupe's definitely not dumbing it down when it comes to this varsity jacket. Damn, the leather and wool combo looks good in black and white.
THE BAD: Not bad at all. We love the clean styling in this video.
Vegoose Music Festival
WHAT: Vegoose Music Festival in Las Vegas
WHEN: October 2007
THE GOOD: Ehh...
THE BAD: Ill-fitting jeans, complicated graphic tee, and an unnecessary button-up shirt over all of that. Poor form, Lupe.
Swagger x Trilly & Truly: F.O.R Lookbook
WHAT: Swagger x Trilly & Truly: F.O.R look book
WHEN: December 2007
THE GOOD: This is all-black-everything done right. His use of different textures in the same colorway is what makes it far from monotonous.
THE BAD: The bad is that we don't have this Trilly & Truly varisty! Shit's dope.
BET's 106 & Park
WHAT: BET's 106 & Park
WHEN: December 2007
THE GOOD: A khaki jacket with leather accents?! Fire.
THE BAD: Don't know if wearing matching cargo pants was the right move.
Late Show with David Letterman
WHAT: Late Show with David Letterman
WHEN: January 2008
THE GOOD: Nice kicks, cool parka, and is that a Gucci beanie? OK, we see you.
THE BAD: Guests tend to get dressier for late night appearances, and this outfit seems a bit too casual.
Paris, Tokyo Video Shoot
WHAT: "Paris, Tokyo" Video Shoot
WHEN: March 2008
THE GOOD:
The Goyard briefcase is nice. Fancyyyyy.
THE BAD: He looks like a Men's Wearhouse model, lulz. The suit's big and could have used some ironing. For a video shoot, you gots to splurge on a Polo suit.
BBC Switch on BBC2
WHAT: BBC Switch on BBC2 in London
WHEN: March 2008
THE GOOD:
The awesome Trilly & Truly varsity jacket makes another appearance. Can't hate on a winning wardrobe staple. And that Gucci scarf, SWAG.
THE BAD: Nada.
Lollapalooza 2008
WHAT: Lollapalooza 2008 in Chicago
WHEN:
August 2008
THE GOOD:
A white tux is hard to pull off, but Lupe does it well without looking like a Miami kingpin or a waiter.
THE BAD: An interesting choice for a music festival (especially since he usually goes super casual, even to classier events).
Martin Luther King Tribute
WHAT: A Tribute To The Life Of Martin Luther King in London
WHEN:
April 2008
THE GOOD: We're always cool with Bape.
THE BAD: Snowboard gear to a MLK tribute is not so cool.
2008 MTV Video Music Awards
WHAT:
2008 MTV Video Music Awards in Los Angeles
WHEN: September 2008
THE GOOD: We like how he's adventurous with his frame game.
THE BAD: This equestrian look reminds us of Chris Brown's fashion fail.
Press Room at the 2008 MTV VMAs
WHAT: Press Room at the 2008 MTV Video Music Awards in Los Angeles
WHEN: September 2008
THE GOOD: Are those waxed cotton jeans? They're pretty raw.
THE BAD: 'Sup with those buttons? Shit's too hard to wear.
5th Annual Peapod Foundation Benefit Concert
WHAT:
5th Annual Peapod Foundation Benefit Concert in Los Angeles
WHEN: February 2009
THE GOOD: This red varsity jacket is another banger from Lupe's own clothing line, Trilly & Truly. The T&T crewneck is dope too.
THE BAD: We can't even say that the bucket hat is bad because he pulls it off so well. Salute.
51st Annual Grammy Awards
WHAT:
51st Annual Grammy Awards in Los Angeles
WHEN:
February 2009
THE GOOD:
The tux jacket is longer than what we'd go for, but it works for Lupe. The addition of round glasses and sneakers makes this a quirky but cool combo.
THE BAD: Not so bad.
Y-3 Autumn/Winter 2009-2010 Fashion Show
WHAT:
Y-3 Autumn/Winter 2009-2010 Fashion Show during Mercedes-Benz Fashion Week in NYC
WHEN:
February 2009
THE GOOD: Can't go wrong with good quality frames, beanie, jacket, and raw denim.
THE BAD: Whoever Kanye's looking at must look awful because he looks disgusted.
Swagger Magazine
WHAT:
Swagger Magazine
WHEN:
April 2009
THE GOOD:
We're all about a well-fitting pair of jeans. He's also stunting with that watch.
THE BAD: Mismatched sneakers aren't necessarily good, but it makes for a cool photo here.
Backstage at Y-3 Spring 2010 Fashion Show
WHAT: Backstage at the Y-3 Spring 2010 Fashion Show in NYC
WHEN:
September 2009
THE GOOD:
The print on the shirt is cool, but the fit is too big on him.
THE BAD: AHAHHAHAHAHAH AND ARE THOSE SHANTS?
History's premiere of "The People Speak" in NYC
WHAT:
History's premiere of "The People Speak" in NYC
WHEN: November 2009
THE GOOD:
Seriously, Lupe has the best varsity jackets. This one goes hard in plaid.
THE BAD: The whole ensemble is super fresh. Nothing bad here.
Sean "Diddy" Combs' Birthday Celebration in NYC
WHAT:
Sean "Diddy" Combs' Birthday Celebration in NYC
WHEN:
November 2009
THE GOOD: The good thing is we know who to hire as our chauffeur if we ever get a Maybach. Ha!
THE BAD: The "Driving Miss Daisy" look should be left in the movie.
The Premiere Screening of "Summit on the Summit: Kilimanjaro"
WHAT:
The Premiere Screening of "Summit on the Summit: Kilimanjaro" in NYC
WHEN:
March 2010
THE GOOD: We love camo, we love plaid, and we're all for mixing prints, but...
THE BAD: Not sure if this is what we want to look like when we do it.
I'm Beamin Music Video
WHAT:
"I'm Beamin" Music Video
WHEN: April 2010
THE GOOD: This is a really cool shot from the video. He really is beamin' even in all black and even more black in the background. And peep that chain!
THE BAD: N/A.
Louis Vuitton Fashion Show
WHAT:
Louis Vuitton Fashion Show at Paris Menswear Fashion Week Spring/Summer 2011
WHEN:
June 2010
THE GOOD:
All-gray-everything looks clean. Remind us to invest in more neutrals.
THE BAD: Two style stars in one photo? Not bad.
Big Day Out Festival
WHAT:
Big Day Out Festival in Aukland, New Zealand
WHEN:
January 2011
THE GOOD:
The camo fan does it right this time. We like the classic military print paired with clean white shirts.
THE BAD: All good here!