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Jul 8, 2016 10:31 EDT

Big & Tall Men’s Clothing Line and Subscription: The Winston Box produces trendy clothing for Big & Tall men which they sell via a monthly subscription service. Sizes XL and above.

iCrowdNewswire - Jul 8, 2016

Big & Tall Men’s Clothing Line and Subscription


The Winston Box produces trendy clothing for Big & Tall men which they sell via a monthly subscription service. Sizes XL and above.

About this project

It all started with a sponsored ad on Facebook.

The entire ensemble was very well put together. A sharp pair of gray flannel trousers, a purple pin check shirt with contrasting paisley lining on the inside of the collar and cuffs, and a classic black merino wool sweater. A great pair of black monk straps and a belt with a box buckle rounded out the look.

So our Founder grabbed his credit card and tried to order his very own curated monthly clothing box, only he couldn’t find the size he was looking for. So he went to another subscription service… and another… and another. The Big & Tall man had once again been overlooked by the fashion industry.

It was time someone did something about it.


“A lot of people don’t belong [in our clothes], and they can’t belong. Are we exclusionary? Absolutely.” – Mike Jeffries, former CEO of Abercrombie & Fitch  

Ask the average Big & Tall man what they hate most about shopping for clothes that fit and you are bound to get quite a few answers, many of which may not be fit to print. They typically fall into one of these categories:  

  • Major clothing labels don’t design for us and major retailers don’t cater to us.
  • Major retailers carry limited selections and charge extra for “extended sizes.” 
  • High-end Big & Tall stores have designer merchandise but at designer prices.
  • Bargain Big & Tall stores are budget friendly but at the expense of quality.
  • Clothing is designed for function and not form. Styles are dated and uninspired.
  • Inconsistent sizes between labels. A 3XL for one brand could be a 5XL for another.
  • The most popular styles, sizes, and colors sell out very quickly.

Monthly clothing subscriptions should be able to address many of the pain points that Big & Tall men face. Unfortunately, because most of these services curate other brands and labels, they experience the same sourcing challenges that retailers do. There just aren’t enough fashion-forward labels designing for the Big & Tall man.

Until now.


The Winston Box is a new Big & Tall men’s clothing line distributing direct-to-consumer via a monthly clothing subscription service. 

Think of us as:

  • Trunk Club for men with junk in the trunk.
  • Five Four Club for the 5′ 4″ chub.
  • Bombfell for the big fella.

Every month we produce an exclusive limited run of fashion-forward casual, classic and contemporary looks in a variety of colors and sizes. We then match those garments with the size and style preferences our members provide to us and ship them a box of 2-4 pieces each month.

No more styles that make you look like your dad, or a lumberjack. No more guessing games about which brands run small. No more backorders on black, gray or navy blue. No more overpaying for quality.


Controlling the design, manufacturing and distribution of our private label gives us some significant advantages over retailers in the Big & Tall market segment and the monthly subscription services that have yet to embrace extended sizes.

Look, Fit, Availability and Price

By designing our own clothing, manufacturing a limited monthly inventory, and cutting out the middleman by shipping direct-to-consumer, we can deliver an end product that addresses the 4 major areas of concern for the Big & Tall shopper.

Seasonal Collections

Since The Winston Box does not curate other brands or labels, the content of our boxes are not dependent on what deals we can cut or which designers have excess inventory they are trying to move. This gives us the ability to take an organic and holistic approach to our collections.

Our emphasis is on helping men build interchangeable wardrobes. This is why we design our collections one season at a time, ensuring that all three monthly boxes from a season are coordinated with each other. This gives our members the ability to build multiple looks and layers by mixing and matching different pieces. This is a revolutionary concept for the monthly clothing subscription model.

Quality Materials and Workmanship

We proudly manufacture our garments in Peru.

Peru is world-renowned for its textile industry. Peruvian Pima cotton is highly regarded for being soft, durable and resistant to piling. Some designers charge $145 for a simple t-shirt made from this material. Wool, alpaca and vicuna are just some of the other high quality fabrics that are sourced in Peru.

Just as impressive as their textile industry, Peru is the market leader in South America for quality workmanship in the garment manufacturing sector. According to Sourcing Journal, Peruvian manufacturers are highly sought after by major labels like Ralph Lauren, Marc Jacobs, Hugo Boss, John Varvatos, Lacoste, Burberry and others.


If it were up to our Chief Customer Officer, every man would be wearing seersucker suits and bowties. However, guys have their own individual style and The Winston Box has identified three major categories for our members:

  • Casual
  • Classic
  • Contemporary

When our members sign up, they complete an online style profile and provide us with their size and style information. We also ask additional questions about their likes and dislikes, and use all of the data collected to build their wardrobe from the collection we design and manufacture that month.

Here are a few samples of items available at The Winston Box:

Casual Style

Jeans and a t-shirt is the quintessential American look and, for some of our members, the only look. Our focus is on delivering a high-quality incarnation of these comfortable staples, while introducing seasonally-appropriate pieces to create a more versatile wardrobe.

Sample Casual Look Produced by The Winston Box
Sample Casual Look Produced by The Winston Box
  • Fleece-lined hoodie
  • Gray thermal
  • White cotton t-shirt
  • Light wash jeans

Classic Style

Classic style is our most versatile product line, with wardrobe choices that are appropriate in almost any setting. Our updated spin on these timeless classics will keep our members looking good, but never boring.

Sample Classic Look Produced by The Winston Box
Sample Classic Look Produced by The Winston Box
  • Gray shawl cardigan
  • Light blue graph check shirt
  • Flat front chinos 

Contemporary Style

Big and bold. That describes some of our members, and it describes our contemporary style line. Trendy clothing. Adventurous patterns and textures. A robust color palette. An “in your face” to conventional style guides that try and limit big men to darker colors and slimming stripes.

Sample Contemporary Look Produced by The Winston Box
Sample Contemporary Look Produced by The Winston Box
  • Purple gingham check shirt with contrasting inner collar and cuffs
  • Black and grey shirt in modern pattern
  • Relaxed-fit black jeans
  • Grey slacks with tapered legs

Size Chart



Much like the other subscription services that are out there, The Winston Box makes it very easy for you to get a little style in your life.

It starts by logging on and creating an online style profile. This is where our members share with us their size information and measurements, their prefered looks and styles, and tell us about their personal fashion don’ts (like not wearing pink shirts or loud pants).

This would also be the time when a members enter their payment information. The Winston Box is $75 per month, with an easy exchange policy and no contracts. Cancel at any time.

Once a member sends us their information and makes a payment, our style team puts together some garments from our monthly collection and ships it to you. 

We have an easy exchange policy for any sizing issues. However, since our clothes are designed specifically to have consistent sizing, we don’t anticipate you experiencing any major issues with fit.

***** It is important to note that Backers ARE NOT AUTOMATICALLY ENROLLED into a monthly subscription by backing our project. However, backers HAVE THE OPTION to enroll in a subscription after the Kickstarter campaign is over, *****

The Winston Box has a very aggressive funding goal of $50,000. The funding for the project addresses three very specific areas that are critical to the success of our project and our ability to fulfill our Kickstarter rewards.

  • Business Intelligence and Information Technology: as we build out the algorithms that form the engine of our online style profile.
  • Manufacturing: Securing the raw material and the human capital required to begin manufacturing our Big & Tall clothing label.
  • Distribution and Logistics: Importing our clothing, warehousing, order fulfillment and shipment to the end user.

In order to reach this funding goal, we have devised 5 different funding levels with associated rewards:

As seen in the boxes above, there are multiple funding levels.

Reward 1 is perfect for those individuals who want to help move our project along, but don’t have a need for Big & Tall clothing and don’t know anyone that does.

Rewards 2-3 are for those backers who want to start out a little bit small. For supporting our project, they will receive a custom box of clothing. These individuals will save anywhere between $10-20.

Rewards 4-5 are for those backers who are looking for great value. For supporting our project, they will receive three custom box of clothing. That’s one box a month for an entire season. These individuals will save anywhere between $50-75.

***** It is important to note that Backers ARE NOT AUTOMATICALLY ENROLLED into a monthly subscription by backing our project. However, backers HAVE THE OPTION to enroll in a subscription after the Kickstarter campaign is over, *****

The Winston Box takes its name and inspiration from Sir Winston Churchill, the former Prime Minister of the United Kingdom. Churchill epitomized what it meant to be a British gentleman and, despite his stocky build, was one of the most stylish men to ever grace the planet. 

It is his example that fuels our mission to dispel the myths that style and size are mutually exclusive and that fashionable clothing must end at a 42 waist or an XL shirt.  

Sir Winston Churchill Memorial - Toronto, Canada
Sir Winston Churchill Memorial – Toronto, Canada


“We make a living by what we get, but we make a life by what we give.” – Sir Winston Churchill   

If we are to make our living citing Winston Churchill as our inspiration, then we must also follow his example and make a life by generously giving back. This is why The Winston Box will be focusing on two unique projects that will bring both money and clothing to those in need.

PROYECTO PERU: Our founder, Wil Cuadros, is a first-generation American born to Peruvian parents. Many of his relatives still live in Peru and the country’s culture, food and people are his passion. This is why $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.

CLOTHING DONATIONS: Each month The Winston Box designs, manufactures and distributes a limited-edition collection to its members. In order to accommodate new membership enrollments and size exchanges we intentionally produce more than is required to fulfill our orders. Select excess inventory at the end of 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 continue to change.


Risks and challenges

We have identified two critical areas where potential obstacles could come in to play.

First, in order for our customers to provide us with their size and style preferences, they must have access to our Winston Box online style profile. This is the most critical deliverable post-funding. Any delays in rolling out the back end of our website will result in a domino effect causing delays in manufacturing of our signature label and distribution to the end user.

That being said, we feel that we are well-positioned to deliver the style profile on time. The logic behind our style profile, in addition to the workflow for our account and subscription management system, has been in the works for quite some time. The timeline that we have for implementation, based on the size of our team and the scope of work to be completed, is quite generous and has some padding built in for unforeseen circumstances.

Second, as with any large scale overseas manufacturing operation, there is always the possibility that disputes or issues arise that would compromise our ability to deliver on time or at the level of quality that meets our expectations.

However, we feel very comfortable in the capabilities of our overseas partners. Our vetting process to identify reputable Peruvian contractors started months ago at the Peru Moda industry trade show where we connected with manufacturers who have worked with major labels and retailers in the United States. Their familiarity with the expectations of the US market is a plus.

Also, we already have dedicated project managers in country to ensure quality control at all phases of our operation, from design and pattern making to cutting, assembling and finishing.

Finally, our founder will be leaving his wife and kids behind for a few months and taking up residence in Peru to personally oversee every step of the manufacturing process until all orders are complete and shipped to our first customers.

In conclusion, there is no doubt that we will complete the project and deliver on our promise to get a customized box of clothing to everyone that places an order. Our goal is to get these boxes to our customers on time, and we feel that we have clearly outlined the proactive steps we are taking to ensure that.

Contact Information:

The Winston Box

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