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The Winston Box: A Monthly Subscription Clothing for the Big & Tall Man

Image from the Winston Box

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“Think of us as Trunk Club for guys with some junk in the trunk.” Wil Cuadros

I love innovation. Especially as it pertains to the plus size fashion community. And one part of the community that often gets left out are the Big & Tall men! I have been watching, we have JUST shed a light on a few making waves, and today, I am so excited to share with you the latest news coming out from the Big & Tall Market: The Winston Box!

For the Big & Tall Man: The Winston Box

Now, the Winston Box is still in its Kickstarter phase, so your support is going to be needed to help this service come to life, which is why I am sharing this with you! I love this concept and think this is brilliant! Created by Wil Cuadros, he has created The Winston Box to be the first and only monthly subscription-based clothing service catering exclusively to the Big & Tall man.

Where did this idea come from? Wil breaks it down:

The Winston Box takes its name from Sir Winston Churchill, former Prime Minister of the United Kingdom and one of the most stylish men to ever grace the planet, our goal is to dispel the myth that style and size are mutually exclusive and that fashionable clothing must end at a 42 waist or an XL shirt.

I am here for this Wil!

So let me tell you how The Winston Box works!

For the Big & Tall Man: The Winston Box Each month, they will send their members an “expertly curated box from our private label clothing line, designed in-house and inspired by the most recent trends in men’s fashion.” This allows them to have complete control of the design, manufacturing and distribution process!

You get to choose between three style options! Casual, Classic, and Contemporary! I love this (bounces shoulders) as this is a very innovative way to deliver, address, and solve a few issues with options!

Your subscription to the Winston Box promises:

  • Fashion-forward styling adapted to flatter the Big & Tall man.
  • Quality garments designed to deliver a consistent fit and feel.
  • Preferred sizes, styles and colors that are always available.
  • Competitive flat pricing with no up-charges, regardless of size.

For the Big & Tall Man: The Winston Box

So listen, the Winston Box Kickstarter campaign launches TODAY at 1pm EST/ 10am PST at!

But, if you want to learn more, you can check out!

I already know about three men in my life that need this! ANNNNDDD they go up to a 6XL which fits up to a 64-inch waist! How about that for inclusion!

I do hope this takes off amazingly, so that we have more options and resources for our fellow Big & Tall men!

What do you think? Share this with your fellow Big & Tall Men!! 

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Written by Marie Denee

I am the Editor in Chic of The Curvy Fashionista. Often goofy. Forever emo. Always a Virgo. You can find me somewhere grooving to 90s R&B.

What do you think?


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  1. YAY! Finally a box that actually will assist the big men!xl-6xl(could go bigger). All the others have articles of “big man sizes” that little men believe that are of a hefty size yet waist sizes are no bigger than Target 40’s, and ignore the plumper sized men’s needs. In fact, the larger men, tend to not enjoy the process of going out in public to most store due to size constraints and just not offering “good” clothing. The big men stores are far and few between, so one must make a day of it just to get to one of these stores.

  2. The Winston Box is a great concept! However, they are suffering from a learning curve on international trade. Shipments are severely delayed, I am still waiting my November order. The reasoning is that they are having difficulty receiving their product from Peru due to Customs delays. It may very well be the case but this kind of difficulty should have been understood. Customers are not warned of the delays when placing the orders and nothing on their web site indicates this.

  3. Similar to the other Steve, I would strongly recommend against the Winston box. Lots of anticipation for sub-par design and shady business practices which include not accepting returns, and requiring phone call cancellations (a practice which intentionally increases the barrier to exit)

  4. I received my first Winston Box this week and was totally disappointed – ripped off more like it. I received two hideous pullover shirts and paid $79 for it. One shirt was white with a black breast pocket and black cuffs with a mock neck – I looked like a mime! The other shirt was just butt ugly. Where are the shoes, the pants, the scarf, etc…. only two shirts, you have got to be kidding me. Cancelled!!!

  5. Please do not waste your money on this one. I received my first box and it was horrible. An ugly green and grey polo and a misshapen cardigan sweater. This is a great idea but the execution is just awful. I found out after almost 2 months of emails, phone calls and Facebook messages with no answer… they don’t do returns. You also can’t cancel your subscription on their website, so you have to wait a few months for them to get back to you in order to do that. Meanwhile they keep charging your card. I asked in my response to cancel my account, so let’s see if that take another 2 months before it gets handled. Please don’t spend money with them, you can get the same mediocre clothing in Kmart or any other big and tall store for less money.

  6. I have to say that my experience with this service has also been a big disappointment. I ordered the “trendy” look and got an e-mail letting me know that they’d be sending me a bonus item from last month. I was excited and hoped to wear the stuff they sent to a weekend gathering. The box came, was SUPER light. In it were two very unattractive low-quality t-shirts, one with a sewn-on pocket in a contrasting color, the other with strange patterned shoulders sewn in. I ordered 2XL, but they were easily 3XL or 4XL and hung off me in a very unflattering way. The third “bonus” item was a button down patterned shirt that I would like if it had a shape and weren’t huge on me. Paying $75 for 2 t-shirts I will never wear (except as PJs) and an ill-fitting button down is not what I had in mind. In fact, no one seems to ever receive pants or shorts from these guys at all, which was what I was hoping to get, since those are the trickiest items for me to find in my size. I’m one of those guys who’s just big enough to have trouble getting clothes in normal stores, but not big enough for Big and Tall places, so I was very excited about this service. I was extremely disappointed. Stay away.

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