January 1982

view of american film director spike lee backstage at an emerging designers fashion show (sponsored by polaroid), new york, new york, circa 1982. (photo by thomas iannaccone/getty images)
Thomas Iannaccone

Life is good when you’re in a timeless, well-fitting gray suit, layered over a sheeny shirt and tie, glass of bubbly in hand.

September 1986

new york, ny september 28: spike lee, the director of shes gotta have it, poses at the greenwich village theater in new york on sept. 28, 1986. (photo by ted dully/the boston globe via getty images)
Boston Globe

It’s an absolute power move to sport your own merch, especially when it looks this good.

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January 1989

portrait of american film director and actor spike lee (center) on the set of his film do the right thing, new york, 1989. among the cast behind him is actor danny aiello (left). (photo by anthony barboza/getty images)
Anthony Barboza

As Mookie in his pivotal third joint Do the Right Thing, Lee embraced the late ’80s/early ’90s trend for multicolor.

May 1989

france may 19: cannes film festival during film do the right thing on may 19th, 1989,in cannes,france (photo by alexis duclos/gamma rapho via getty images)
Alexis DUCLOS

Three years before the release of his acclaimed Malcolm X movie, Lee foreshadowed his future with a T-shirt printed with the revolutionary’s moniker.

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December 1989

director spike lee attending the premiere of blaze on december 13, 1989 at the ziegfeld theater in new york city, new york. (photo by ron galella, ltd./ron galella collection via getty images)
Ron Galella, Ltd.

Now, that’s a coat and a half. It’s giving Jonathan Anderson’s Loewe 24 years before that appointment. The gloves are also pretty great (is that a mix of brown leather and black nylon?).

March 1990

director spike lee attending 62nd annual academy awards on march 26, 1990 at the dorothy chandler pavilion in los angeles, california. (photo by ron galella, ltd./ron galella collection via getty images)
Ron Galella, Ltd.

Wearing that black suit and white shirt again? Make your colourful scarf your secret weapon, and why not throw a hat on while you’re at it.

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May 1991

le réalisateur spike lee en mai 1991 à cannes, france. (photo by pool arnal/garcia/picot/gamma rapho via getty images)
Pool ARNAL/GARCIA/PICOT

Pure ’90s nostalgia, with the ankh necklace and the other less-easy-to-describe necklace really bringing the entire look together.

1992

washington, dc. 1992 spike lee in washington dc. credit: mark reinstein (photo by mark reinstein/corbis via getty images)
Mark Reinstein

The ankh is back for ’92, atop an effortless collarless blazer, made more casual by a Malcom X cap—here, an explicit nod to the biopic which released that year.

February 1996

model kiara kabukuru wearing a white silk trenchcoat, by michael kors, standing next to actor and director, spike lee, smiling. (photo by arthur elgort/conde nast via getty images)
Arthur Elgort

Gotta hand it to Vogue: this is a ‘fit and a half. It’s like what we’re all wearing now, piecing remnants of fading trends—gorpcore, dadcore, Y2K, Aimé Leon Dore-mania—together in a super refreshing way.

October 1998

bronx, ny october 7: filmmaker spike lee attends game two of the american league championship series between the cleveland indians and the new york yankees on october 7, 1998 at yankee stadium in bronx, new york. (photo by sporting news via getty images via getty images)
The Sporting News

The famous red Yankees cap, styled with a cozy, Knicks-flavored Nike ACG fleece.

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October 2000

boston october 9: filmmaker spike lee is interviewed by a globe reporter at the four seasons hotel. (photo by chitose suzuki/the boston globe via getty images)
Boston Globe

Without the telltale flip phone and grainy quality, you’d believe this photo was taken yesterday. That green felt Yankees cap, khaki raglan knit, and beige cargo pant combo feels so right now.

February 2003

paris february 22: american director spike lee stands with his cesar award february 22, 2003 after the cesars film awards at the theatre du chatelet in paris, france. (photo by pascal le segretain/getty images)
Pascal Le Segretain

Everything, here, is intentional. The unusually-rectangle-for-Lee glasses. The is-it-a-tie-is-it-a-cravat accessory. The wide satin lapels. The big cuffs, heightened by the shorter arm sleeves. The straight leg trousers. The well-shined shoes. That’s what we call making an effort.

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April 2003

london april 23: director spike lee arrives at the barbican center for the u.k. screening of his film 25th hour april 23, 2003 in london. (photo by bruno vincent/getty images)
Bruno Vincent

This look tells me that Spike Lee would look very good in, and would probably very much appreciate, clothes by Bianca Saunders. The silhouette and the colors feels very much in line with the British designer’s output.

May 2004

spike lee and wife tonya during opening of the new broadway production of the classic play a raisin in the sun arrivals at royale theatre in new york city, new york, united states. (photo by rj capak/wireimage for people magazine)
RJ Capak

Styled with a shy shrug of the shoulders, this earthy look, delicately finished with tortoise shell spectacles, whispers quiet intellect.

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January 2005

tonya lewis lee and spike lee (photo by lawrence lucier/filmmagic)
Lawrence Lucier

What I want my Winter Wonderland ‘fit for this year to look like.

July 2006

spike lee, director/producer of when the levees broke: a requiem in four acts (photo by jeff kravitz/filmmagic, inc)
Jeff Kravitz

This might be the coolest anyone’s ever looked in a Wimbledon blazer, as Lee has freed the piece of its haughty colouring by styling it with a baggy polo, relaxed trousers, and Knicks-themed AF1s.

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November 2006

united states november 06: basketball: new york knicks fan and celebrity film director spike lee in stands during game vs san antonio spurs, new york, ny 11/6/2006 (photo by al tielemans/sports illustrated via getty images) (setnumber: x76995 tk1 r2)
Al Tielemans

The magic of this ensemble is that he didn’t overthink it. He grabbed a trusty big pony Ralph polo, paired it with some everyday trousers, and finished it off by throwing on some Jordans and a baseball cap. Sometimes, good fashion is really that simple.

April 2007

milan, italy september 24: samuel l. jackson and spike lee arrives at the giorgio armani show as part of milan fashion week spring summer 2008 on september 24, 2007 in milan, italy. (photo by venturelli/wireimage)
Daniele Venturelli

A true mark of style is the ability to seamlessly switch between the laid-back look of sports jerseys and shorts and smarter cord suits and ties.

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September 2007

new york april 11: (l r) long island university provost david steinberg, spike lee and ralph engelman attend the long island universitys george polk seminar to discuss illuminating catastrophe: covering new orleans and darfur on april 11, 2007 in new york city. (photo by andrew h. walker/getty images)
Andrew H. Walker

If I could be anybody at any time, being Spike Lee in a velvet suit and satin tie stood with Samuel L. Jackson at the September 2007 Giorgio Armani show would be high up there.

May 2008

cannes, france may 20: director spike lee attends the miracle at st. anna photocall at tf1 beach during the 61st cannes international film festival on may 20, 2008 in cannes, france. (photo by john shearer/wireimage)
John Shearer

To turn a noughties skater boy ‘fit into a political statement (see: Obama ’08 printed on the tee) is absolutely everything to us.

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