Top sizes to 6XLT. Waists to 64”

The Winston Box

The Winston Box

Curated Garments for the Corpulent Gentleman

Our Story

It started with a Facebook ad.

One evening in January of 2016, as I was having a late-night snack, an ad for a clothing subscription service caught my eye. Not only did the clothes look great but they claimed to have a look for every style and size. So I grabbed my credit card, prepared to make an impulse buy and started practicing my excuse to my wife.

But they didn’t have my size.

Determined to blow money I didn’t have, I started looking into other men’s boxes. Someone had to have my size, right? So I looked at personal shopping services. I looked at all-inclusive services. I took every style quiz and went though every checkout process.

When I discovered that not a single men’s subscription clothing service offered anything I could wear, even though there were thousands of messages on social media from big guys begging these companies to offer their sizes, I decided to start my own company.

When I discovered that most subscription boxes couldn’t be bothered with big and tall sizes because there weren’t enough quality big & tall labels at a reasonable price, I decided to start my own clothing line.

When I discovered that Peru was known for having some of the best cotton on the planet, I moved out there for a few months to hand-select the fabrics we would use and find small-scale manufacturers to make our clothes.

When I discovered these small-scale manufacturers couldn’t meet my strict deadlines nor deliver the quality our customers would demand, I raised some money, bought my own machines, put together a team in Peru, offered them a fair wage (including paid lunches and private health insurance) and I set up my own shop.

So here we are today, a self-funded small-startup on a mission to deliver affordable clothing and consistent sizes at an affordable price. A big & tall men’s clothing company, made by big men for big men, forged from my 42 years of frustration with what the fashion industry has to offer guys like me. A small-batch manufacturing facility churning out a new collection every month, despite the odds. A responsible corporate player, empowering our customers through body positivity and self-confidence, while empowering our team members in Peru through training, mentorship and opportunities.

This isn’t business. It’s personal.

Wil Cuadros, Founder
The Winston Box

Size Chart

Big Big & Tall Neck Chest
XL XLT 17"-17 1/2" 46"-48"
2XL 2XLT 18"-18 1/2" 50"-52"
3XL 3XLT 19"-19 1/2" 54"-56"
4XL 4XLT 20"-20 1/2" 58"-60"
5XL 5XLT 21"-21 1/2" 62"-64"
6XL 6XLT 22"-22 1/2" 66"-68"
Curated Garments for the Corpulent Gentleman