Photographed by Monsieur Jerome.

Becoming a darling of the fashion crowd certainly comes with its upside, and Shayne Oliver knows this better than most. The designer behind luxury-meets-streetwear brand Hood By Air was not only recently nominated for the CFDA’s Swarovski Award for Menswear, but this season he was also selected to present as a Special Guest designer at Pitti Uomo, the kickoff of the menswear fashion season.

Held in the gardens of a stunning Italian villa dating back to the 1400s, the show featured male models adorned in high heels and hair extensions to say nothing of the human hair applied to their eyelashes and eyebrows—styled to play off the overall theme of this special Italian capsule collection’s duality. Studied and spotaneuous, tailored and unbottoned, old world and new, X and Y. [The HBA collection is] “a strong statement on the concepts of gender and social class. And also of power, beauty, and identity,” noted Lapo Cianchi, head of communications and special events for Pitti’s parent company.

Details like cut-outs and drop-back trousers (picture the look of sagging pants, draped to be sure they actually stay up!) in hues including lavender and soft pink made a strong statement about the fluidity of gender constructs and the mutability thereof.

Below, our exclusive window into the Hood by Air backstage setting—an olive garden in the hills of Tuscany—where Shayne prepped models for their runway moment. Before you step back into non-catwalk reality, be sure to check out the current HBA collection on

HBA BTS Shot 1
Final touches as the show is about to begin.

HBA Behind Scenes 5
Model casting played a big role in the show and set it apart from other presentations at Pitti.

HBA Behind Scenes 2
The completed makeup, which continues to take a look at gender expression through an alternate use of hair extensions.

HBA Behind Scenes 6
Shayne makes a last minute adjustment to one of the outerwear pieces.

HBA Behind Scenes 3
Models await approval on their completed looks, including the finale look in the center.

HBA Behind Scenes 4
All the looks were paired with Shayne’s take on a men’s heeled boot.

HBA Behind Scenes 7
Shayne Oliver consults with a dresser. The model wears a net to protect his intricately braided hairstyle – which included lavender grosgrain ribbons in the braids–until showtime.

HOOD BY AIR Stencil Graphic Poplin Shirt / HOOD BY AIR “The Jean” Pants / HOOD BY AIR Atomic Bomb T-Shirt / HOOD BY AIR “The Jean” Pants / HOOD BY AIR Double-Zip Drawstring Hoodie / HOOD BY AIR “The Jean” Pants