Style History: Lupe Fiasco

Image via Complex Original

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?

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.

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.

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.

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?

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.

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.

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.

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.

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.

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.

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.

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.

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.

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).

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.

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.

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.

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.

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.

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.

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.

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?

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.

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.

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.

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.

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.

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!