Sat. Feb 1st, 2025

Randy McDonald relaxes at his vintage clothing store, exuding an air of timeless style, impeccably dapper in a striking Houndstooth jacket, red turtleneck, artfully ripped black jeans and Buster Brown-esque black-and-white saddle oxfords, reminiscing back in time with juxtaposing ease on how his love of fashion came to be.

Randy “Silly Billy” McDonald, relaxing at his vintage clothing store in Jackson, Wedneday, Jan. 15, 2025.

“So, funny story,” he begins, smiling and shaking his head. “I always tell men that come into my store that the reason I’m probably so much into fashion has to do with my grandmother, my mother and my aunt. Yep, those three women,” his smile widening.

“We would get up on Saturday mornings, go have breakfast, then head to the mall. Let me tell you, they would go mad. From about 10 o’clock until 2 o’clock, we shopped. Then, we’d stop, have lunch, and repeat the process until around six in the evening. Then we would have dinner and very possibly do a third round dash through the stores before heading home around 9 o’clock.”

McDonald pauses, gazing around his store Silly Billy’s, located at 5482 N. State St. in Jackson.

A look inside Silly Billy’s vintage clothing store in Jackson.
Vintage clothing store owner Randy McDonald arranging merchandise at his Jackson store, Silly Billy’s. Credit: Vickie D. King/Mississippi Today
Vintage jewelry at Silly Billy’s in Jackson. Credit: Vickie D. King/Mississippi Today
Vintage jewelry at Silly Billy’s in Jackson. Credit: Vickie D. King/Mississippi Today

“I learned a lot from those women. They were always stylish. I picked up that looking good makes you feel better about yourself,” he says quietly, nearly in a whisper.

“Here’s style for you. My grandmother…,” he says, remembering. “She wanted a very specific car… a black Cadillac with black leather interior and a black rag top, trimmed in gold. When the dealership found it and called her to come pick it up, she decided that first, she needed a new outfit to wear with her new car.”

“My grandmother went to Mobile and had a lady that sewed clothes for her create a two-piece ivory set that had lace on top and beading to match that Caddy. Here’s the kicker. Come Sunday, she put on her new two-piece ivory set to match her all black Caddy to drive to church,” he says with a gleam in his eye. “The church was probably fifteen to twenty feet away from her house.”

McDonald chuckles while arranging items in his store at the memory of his grandmother’s panache, pointing out different eras in clothing from the groovy 60s to the Disco 70s to 90s hip hop.

Vintage clothing and artwork at Silly Billy’s in Jackson.
Silly Billy’s, a vintage clothing store in Jackson, is a step back in time, when all the rage in apparel was bell bottoms to platform shoes, wrap dresses to big lapels.
Go-go boots, platform shoes, wedges, Oxfords and frilly boots at Silly Billy’s, a vintage clothing store in Jackson. Credit: Vickie D. King/Mississippi Today

“The idea behind Silly Billy’s and why I go by Billy instead of Randy, is because Billy pays the bills,” McDonald says, still laughing. “The whole thing derived from sitting down with the original store owner and trying to come up with names. We kept coming up with all these crazy names. Then I remembered a funny story he’d told me about how in his family, they would say, “silly Billy,” instead of a curse word. It was their way of getting your attention when you were doing something or saying something incorrectly too. I just love the fact that they would say, “Oh, you’re being such a silly Billy.” For whatever reason, it resonated with me and just stuck,” he says, smiling, gesturing with a sweep of an arm. 

From bell bottoms to floral prints, platform shoes to disco flare, plus accessories can be treasures found at vintage clothing store, Silly Billy’s in Jackson.
A look inside Silly Billy’s vintage clothing store in Jackson. Credit: Vickie D. King/Mississippi Today
Silly Billy’s owner Randy McDonald, with a sequined mini-skirt and other vintage clothing at his Jackson store Credit: Vickie D. King/Mississippi Today
“Back in the day, who didn’t have a purse like this. If you need to step back in time, come see me. I can get you there,” said Randy McDonald, owner of Silly Billy’s vintage clothing store in Jackson.

“Everybody always paid attention to that name. I knew, too, that I was onto something when my brother told me the name is so different and unique, and it makes you laugh.”

“I inherited the store from the original owner, who was retiring. I had another job, and I often just helped out as the cashier or wherever, doing whatever I could. Then, the place where I was working closed down.”

“The owner said, ‘”‘Come and work for me. Give it a year, see what happens.’ And so I did. Before I knew it, one year turned into two, two turned into three… now, here I am, almost 10 years in,” he says, smiling warmly.

Randy McDonald is the owner of Silly Billy’s, a vintage clothing store in Jackson, Wedneday, Jan. 15, 2025.
Randy McDonald’s personal touches in decor at his vintage store, Silly Billy’s in Jackson.
A walk back in time in platform shoes, “Jellies,” wedges, Oxfords and frilly boots at Silly Billy’s, a vintage clothing store in Jackson. Credit: Vickie D. King/Mississippi Today

“Here’s what I’ve learned over time. My items always tell people, we all fall under the umbrella of thrift. There are a few different arms to that though. You have donations, which will be similar to say, a Goodwill or Salvation Army. You have consignment, like a Repeat Street. Then there’s me. I’m the lone wolf here in Jackson because I go and purchase select items that I want to sell. I resell them in my store so I’m the only store that actually has to purchase up front. I do accept donations, but I don’t get donations like the others I mentioned.”

“My idea is to sell clothing and accessories at a price that pretty much anyone can afford.”

Silly Billy’s is open Wednesday – Saturday, 10 a.m. – 6 p.m.

Social Media: 

Instagram – @SILLYBILLY’SLLC

Facebook – Silly Billy’s LLC

Website: http://silly-billys-llc.myshopify.com

Phone: (601)287-4949

The post Randy McDonald at Silly Billy’s offers vintage style with a smile appeared first on Mississippi Today.