Taylor was once a trendy early-'00s kid in layered tees and slouchy jeans. Here, Teyana Taylor at the New York Hip-Hop Festival S.P.I.N. Awards, November 2006.
Ever a fan of skater sneakers, Taylor continued to pair them with any and every look; here, on TRL in New York, New York, November 2008.
In a flouncy silver minidress with sneakers and ultra-teased hair, Taylor celebrated the launch of a new MAC Cosmetics line in New York, New York, March 2008.
In Lacoste — at Christian Siriano Spring 2010 — Taylor starts appearing at fashion week, hinting at her open embrace of the fashion world to follow. In New York, New York, September 2009.
A little sleeker and more understated, Taylor opted for an equestrian look at the Nu Pop Movement watch launch in Atlanta, Georgia, November 2009.
Short shorts, thigh-high boots, and a graphic tee make a departure from Taylor's previous looks, albeit still with a street-ready edge. Here, at the opening of Fendi in Los Angeles, California, October 2010.
For the premiere of 'Madea's Big Happy Family,' Taylor went fully formal (no sneakers in sight) in a slinky black dress in Hollywood, California, April 2011.
By 2011, Taylor seemed to embrace a wardrobe that was a bit more classically feminine, here, in a striped body-con dress with leather vest at a Reebok event in New York, New York, July 2011.
Biker with an ultra-feminine edge, Taylor pairs a Y-3 leather jacket with leather pants and a pair of metallic Louboutin pumps in Los Angeles, California, October 2011.
Around the time that she began working with Kanye West — here, at the 2012 Cannes premiere of 'Cruel Summer,' his film project with the Doha Film Institute — Taylor also started experimenting with beauty. A blush pink lip and loose, easy pony offset the glamor of her gown.
Taylor paired eggplant lips with an eggplant dress at the VMA pre-party hosted by G.O.O.D. Music, her new label, in Los Angeles, California, September 2012.
In a 'Wave God' crop top (Taylor seems ever the fan of a bit of tasteful underboob) with leather track pants and sneakers, Taylor takes streetwear to stage wear for a performance at the BMI Unsigned Urban showcase in Atlanta, Georgia, April 2013.
Taylor debuted new hair and an edgy new all-black uniform for the New York premiere of 'Beyond the Lights,' November 2014.
Taylor coordinated with husband Iman Shumpert at an event in New York, bringing a chic new androgynous meaning to couple's wear — here, in March 2016.
Taylor's high-waisted red-orange pleated pants narrowly missed clashing with the notorious orange carpet at the Nickelodeon Kids' Choice Sports Awards in Westwood, California, July 2015.
Taylor wore a Hood By Air wetsuit to the designer's Spring 2017 show, inaugurating a new, adventurous, post-"Fade" era in her personal style. In New York, New York, September 2016.
Ever a fan of the crop top, Taylor also went for covetable beachy locks at the Baja East show (wearing Baja East x Minions) in New York, New York, September 2016.
Sleek hair, neutral makeup, boxy separates — Taylor goes incognito as a Vera Wang girl at the designer's Spring 2017 show in New York, New York, September 2016.