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Reserve a Fitting

Complimentary fittings. Personal service.

(540) 403-0353

The shop and the dog.

Independent menswear on Winchester Street, named after a much-loved French Bulldog.

The shop

A clothier, the older way.

A shop that measures before it sells, tells you the truth about the fit, and knows we will see you again for years.

Like a loyal companion, we are there for every aspect of your life. From start to finish, we have you covered, literally.

Hands set a pin at the lapel of a navy herringbone sport coat on a tailor’s dress form, a yellow tape measure over its shoulder.
The planned Winston James interior looking toward the entrance: green counters where an assistant hands a folded shirt to a smiling customer, tables of folded knitwear and ties, rails of jackets, and a man with a coffee in an armchair by the windows.
James
Five sport coats on dark wooden hangers along a brass rail against the deep green panelling: a blue chalk stripe, a charcoal herringbone, a tobacco moleskin, a cream gun-club check and, nearest and turned into the window light, a navy jacket with a cream windowpane. A navy silk foulard tie hangs over the rail end.

James.

When the opportunity presented itself, Fredericksburg was a dream location for the fifth store within The Clothing Commission. But it didn’t start there.

James started working at R. Coffee Ltd in Lynchburg while he was a junior in college. Rick Coffee was an amazing mentor, friend and business partner. He taught James the ins and outs of this business, and he always wanted to have more stores. Unfortunately, Rick passed away in 2025 and never got to see the growth of the business.

But the best part of this industry is the loyalty and companionship it brings. That is what Rick taught James, and it is one of the main reasons James wanted to name this store after his most loyal companion, Winston.

Winston

The name over the door.

Winston was James and his wife Cassady’s first dog after they were married. He wasn’t just their pet. He was part of the family.

One of the reasons the store is named after him is that he embodied everything it means to serve, and in this industry that is sometimes lost.

Winston, a cream French Bulldog with a dark muzzle and upright ears, lying on a wood floor with his front paws forward and his head tilted, in window light.

He was loyal, like we are to you. He was a companion, like your clothing from us will be for your life. He was family, like you all will be to us.

There is nothing more important to us than being a part of your families. We want to dress you, your children and your grandchildren for generations to come. Please allow us to earn your loyalty.

Winston, a cream French Bulldog with a dark muzzle, lying on painted porch boards in low afternoon light.
Five

Our shops.

  • Winston James MenswearFredericksburg
  • R. Coffee LtdLynchburg
  • DavidsonsRoanoke
  • S.H. FranklinCharlottesville
  • B. JordanWilliamsburg
Visit

Come and see us.

When the doors open you are welcome, and so is anyone whose opinion you trust.

Reserve a FittingFind the Shop
A dark-haired man in a camel overcoat over a navy sport coat and open white shirt walks toward us along a brick sidewalk beside a cream brick wall in low afternoon sun.
A closed green leather appointment book with a brass pen across it and a coiled tape measure beside it, on the shop’s wooden counter in window light.

Reservations open soon.

We are still getting the shop ready, so the fitting book is not open yet. Until then, call us. We are glad to talk through what you have in mind.

Call (540) 403-0353Find the Shop