Benjamin Bradshaw – Queer Chicago’s Eclectic Fashionista

Originally from Florida, Benjamin Bradshaw, 22, always had eye for  eclectic fashion. 

“I was trendy for Florida, but, dude, I worked at Hollister when I was 17.
I moved to Chicago for school in Fashion Merchandising but I’m definitely moving in the direction of entrepreneurship.  About a year ago I was randomly approached in public by a local stylist to do some random modeling and I got to wear the clothes of an amazing wacky local 80’s & 90’s vintage store named KokoRokoko. 

I went to the shop after the show ended, fell in love, and and forced them to take me as an intern.  I started doing windows for them, then we became best friends, then I just randomly began buying for them without asking because I understood their wacky style… they liked everything I brought in & they’d pay me the exact money or it. 

I slowly started keeping the most amazing garments I found and at some point I realized I could make money off of my closet full of ridiculous sheer dresses and jumpsuits.  It’s been a month of selling but I’m confident that my specialized goods have enough customers… & everyone who visits falls in love whether or not they’re ballsy enough to wear the clothes out.”

Benjamin calls his clothes…
Vintage Party Gear For Ladies Of All Genders.  

“I go to a lot of gay dance parties, like Chances Dances , so I’m stocking dance wear, mainly, for gay guys and girls. It’s a bit eccentric;  leaning towards the feminine side.

Wacky shit: body suits, sequins, sheer stuff. Right now, I have about  80-90 solid pieces, plus accessories.  And still shopping –  still adding  on.  I try to pick stuff that my grandma would’ve worn in the ’90s—lots of really horrible floral prints and crazy stuff. It’s very sill. It’s meant to be fun!”

SisterMan is officially an Etsy-based business  online , which just launched this month. So new things are being added all the time.  

Check out the Sisterman blog for lots of updates and see what’s happening and where he’ll be showing his collections next. 


“I  set up at The Bonanza  this past month –  a monthly vintage sale  that is held at Berlin nightclub.   It was set up for local brick-and-mortar shops & Etsy vendors a few months ago & it works because it’s fairly constant.  There are a few other vintage sales like it, but it’s nice for me because it’s at a gay club. I am doing something at Heaven Gallery  in Wicker Park and lots of other stuff in the coming months. And people can always contact me through the blog and Facebook. “


I just quit my job & I’m trying to up the ante with Etsy & build clientele in the local gay community.  This summer I’ll be at lots of gallery, club, and outdoor sales and I’ve extended an invite to the DJ’s and promoters of a few gay parties to use my goods in exchange for publicity. 

Yesterday I helped a friend with a little movie project here locally and got to wear some of my clothes for that.  And of course, I’ll be out dancing and partying in the name of networking.”

Find  Benjamin and SisterMan  on FaceBook  
or  the SisterMan blog .

The Best of Gay Chicago