Meet The Winston Box, A Big Men’s Clothing Subscription Service

The Winston Box

Over the years, you’ve been asking us where to find the big men’s subscription clothing services. Until recently, the answer was: there are none. In the last few months, that’s started to change, as we’ve seen some emerge at various levels of quality, inventory, and niche. There just hasn’t been one that’s blown our socks off yet, but the latest entrant to the category, called The Winston Box, looks promising.

What is The Winston Box?

The Winston Box is a monthly subscription service catering exclusively to the plus size, or big and tall man, with sizes ranging from XL to 6X and 42 to 64 waist. They know that it’s hard to find clothes that fit, and harder yet to find clothes you actually want to wear in your size. If you’ve ever used a custom subscription service (think Trunk Club or Five Four), this won’t be too new to you. Simply go to their site, create your profile (including sizes, preferences, important info), and the folks at The Winston Box will put one together for you. Wait patiently for your box to arrive, and when it does, voila! You’ve got 2-4 new pieces of clothing that fit. Something not right? They have an easy exchange policy that helps ensure you get what you need. Boxes will run $75/month, with no contract required, which means you can use the service as much, or as little as you want.

The Winston Box Sizing

What About Size, Quality, and Style?

We’ve all slapped down money on a piece of clothing, only to wear it a few times and have it fall apart, or to find that ultimately, it doesn’t really fit your body well. According to The Winston Box founder, Wil Cuadros, this won’t happen with his clothing. “We are manufacturing our own garments because size consistency is so important to us.” By designing and manufacturing a limited monthly inventory, they plan to have more quality control over their product.

When it comes to style, Wil understood that not everyone likes the same look, so The Winston Box will offer casual, classic, and contemporary styles, meaning that you’ll be able to find something you’ll look good and feel comfortable wearing.

The Winston Box Casual Look

The Winston Box Gives Back

As if offering a plus size men’s clothing subscription service weren’t enough, Wil, a 1st generation American born to Peruvian parents, has set up the business to give back to those in need. $1 from each Winston Box sold goes to Proyecto Peru, a refuge in the shanty towns of the capital city of Lima that provides food, clothing, shelter, education and healthcare for up to 50 children at a time. In addition, excess inventory created each month will be donated to charities and hospitals that operate bariatric surgery clothing exchange programs, helping men who are experiencing rapid post-surgery weight loss have access to a temporary wardrobe as their bodies change.

The Winston Box is an ambitious project, but the kind that we need today. You can help Wil make it a reality by sharing and supporting newly launched Kickstarter campaign. You can also visit The Winston Box at their website,

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