Style of the Streets – Stylists to The Stars

The creation of a consciously styled individual image is a vital element within the construction and development of any music star. Within Hip Hop however, presentation of image through fashion even rivals the importance of the music itself. A unique fashion and hip hop harmony which was propelled in-part by Dapper Dan and continued with ventures like ‘Sean John’ by Diddy and ‘Mains’ by Skepta to name just a few, to be aware of fashion and better involved in it, has never been so important to the rappers of today. Now on True Mag we take a look at the stylists responsible for dressing the best in the game, from 21 Savage to ASAP Rocky.


Aleali May

A fashion consultant and stylist to the likes of Kendrick and Kanye, Aleali May began her fashion footprint through working for Don C and Virgil Abloh’s RSVP Gallery in Chicago while attending Columbia College in 2010. Signing to creative agency ‘The Society Management’ in 2017, Aleali began to collaborate with renowned global brands. In October of the same year, Aleali became only the second woman to collaborate with Nike’s Jordan brand, and the very first to release both men’s and women’s sizing consecutively with the brand. A huge mark in fashion and sneaker history, the “Air Jordan 1 Aleali May” was released with huge success. Going on from this to dress 21 Savage, Playboi Carti and Lil Yachty, May has a powerful influence over the image of hip hop today.

21 Savage styled by Aleali May
Lil Yachty styled by Aleali May


Follow Aleali May on Instagram here.


Matthew Henson

ASAP Rocky’s co-conspirator Matthew Henson joined Rocky in 2012, after meeting him on the set of a photoshoot for Complex Magazine, of which Henson is an editor. Almost a tale of long lost brothers, Henson has largely spoken of the loyalty and trust shared between the pair ever since, explaining that there are no limits to what Rocky will wear, as long as it’s understandable to the audience. Henson describes that although varied, Rocky’s style is incredibly intelligent with a natural understanding and appreciation for fashion itself. Evidenced too by his collaborative relationship with British designer JW Anderson with the pair working under the tag name ‘JWA X AWGE’ it’s clear Rocky has an imperative need to be surrounded by fashion. Henson shares that the key Rocky fit is determined by a great jacket and a well-fitting pant paired with the rarest sneakers you can find.

Matthew Henson and ASAP Rocky

Follow Matthew Henson on Instagram here. 


Lauren Matos

Dressing Wiz Khalifa since 2015, Matos has propelled Wiz onto many of the best dressed run downs of nearly every event, helping him make a name for himself outside of music. Addressing in every interview that finding a fun party shirt is the key staple for a Wiz outfit, Matos says from instantly meeting the pair decided they wanted to keep Wiz’s style young and relaxed at heart, but make it more serious and original of its own. Drawing on ‘a classic, more simplified Lenny Kravitz or something’ for inspiration, Matos says she never wants to detract from the stature of Wiz, who is over 1.93m tall and ‘built for brands like Saint Laurent’.

Lauren Matos and Wiz Khalifa

You can follow Lauren Matos on Instagram here. 


Kyle Luu

NYC-based stylist Kyle Luu has dressed the likes of Travis Scott, Tinashe and Solange. Also one-third of the hip hop creative team behind fashion/lifestyle force ‘The Glam Collective’ Luu first began by styling artist Neon Hitch. Two years later she found herself working with Travis Scott and has now worked with the rapper for over 4 years, even piecing together his 2017 Met Gala look. Specialising in high-low fashion combinations that showcase Scott’s southern Houston roots, Luu pairs camo sets with champion sweats, always to be finished with stackable diamond rings.

Travis Scott styled by Kyle Lum (2017 Met Gala)

You can follow Kyle Luu on Instagram here. 


Whitney Middleton

Chance The Rapper’s stylist of nearly two years, Middleton has formed a perfectly streamlined uniform of boxy jackets to exactly fit Chance. Of course always topped off with his signature ‘3’ New Era cap, Middleton a Chicago girl herself focuses on colour to enhance Chance’s playful but minimalist style. Usually donning her famed electric blue hair colourway, Middleton transfers this informal playfulness to her looks, even putting Chance in a colour-blocked Off-White denim jacket matched with classic Levi’s for Grammys Weekend. Everyone’s favourite boy next door, the image below perfectly illustrates the friendship formed between the playful pair.

Whitney Middleton and Chance The Rapper

You can follow Whitney Middleton on Instagram here. 

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