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The Winston Box Review + Exclusive Discount

The Winston Box Unboxing

The Winston Box is the first clothing box for Big & Tall men, with top sizes to 6XLT, waist sizes to 64W and inseams to 38. They take a subscriber's unique style, color and size preferences and put together a box of 2-3 items from their signature clothing line. Whether you style is basic (Casual), prep (Classic), fashion-forward (Trendy), or you just want to be surprised (Mixed), they can deliver a box of clothing to your door for what you would spend for just one item at a specialty Big & Tall store.


$15 OFF

$15 OFF Your First Box at The Winston Box.
Click button "GET CODE" get $15 off your first box at The Winston Box.

How It Works

Complete Your Style Profile

Get started with your style profile. It takes less than 60 seconds! Give them your preferred sizes, styles and colors. They’ll give you a welcome call once you’ve placed your order to answer any questions you have.

The Winston Box Big & Tall Clothing

They Assemble a Personalized Box

Our experts use your style profile to select 2-3 items from their seasonal collections. The average retail value of each box is $130, but you keep everything they send for just $75.

Get Your Box Shipped Worldwide

Your first Winston Box typically leaves in 2-3 business days. Once you get it you have 15 days to exchange any garment for a different size. Boxes ship monthly after that.

Subscription Options

  • Choose Monthly frequency if you're looking for new threads every month starting today.
  • Choose Bi-Monthly frequency if you're looking for new threads every other month starting today.
  • Choose Quarterly frequency if you only need new threads every 3 months starting today.

What comes in each box?

Each box comes with 2-3 garments, like shirts, polos, jeans, shorts, sweaters, hoodies and everything in between. You will also get the occasional accessory. Some boxes are complete outfits. Some boxes are pieces meant to complement your existing wardrobe or prior boxes.

What style of clothing do they offer

The CASUAL collection is for the ultimate jeans and t-shirt guy. He likes unfussy clothing and you will frequently find him in activewear because he prizes comfort above all else, whether he is going to the local home improvement store or catching a ballgame.

The Winston Box Sample Box

The CLASSIC collection is for the man looking for a modern twist on preppy clothing. He needs a versatile wardrobe that can go from casual Friday to happy hour after work.

The TRENDY collection is for the man who keeps up with the latest fashion trends. He loves to socialize and documents his exploits on social media. He knows that the rules for big and tall men are being rewritten and is looking for a brand willing to say.

The MIXED collection is perfect for the man who is open to trying new looks and styles he wouldn’t have bought on his own. This collection is about expanding both comfort zones and wardrobes. Choose Mix if you are unsure what to get, you can always change your style profile at any time.

Free Shipping

Free Shipping for Your Order at The Winston Box.
Click button "GET DEAL" get free Shipping for your order at The Winston Box.

The Bottom Line

All three pieces in this Winston Box are impressive. They’re all very well made, stylish, and coordinate for easy mix and matching! We were also impressed that all of The Winston Box clothing is made in Peru which is where some of the best cotton comes from.This boxes is worth $130 which is almost double the box cost. At $75 for the entire box, each piece breaks down to cost just $25 each which is a bargain for the high quality! If you’re looking for a men’s big and tall clothing subscription box, we highly recommend you try The Winston Box!

About The Winston Box

The Winston Box Review

Fashionable Looks

Big & tall men know that the bigger the clothes, the more boring the designs. The Winston Box in-house design team is always looking at the latest trends in order to create fashion- forward looks that are not found in most big & tall stores.

Premium Fabrics

Big & tall men know their clothing can sometimes feel cheap. The Winston Box team works with premium fabrics, such as Peruvian Pima cotton, and stretch twill, in addition to working with unique fabrics that aren't typically found in big & tall clothing.

Consistent Sizing

Big & tall men know sizing can vary wildly from label to label. The Winston Box label is made by and for big & tall men, paying close attention to the fit and sizing, which is why their sizing is consistent from garment to garment and box to box.

The Winston Box Casual Collection

Confidence. Delivered Monthly

They are a self-funded small-startup on a mission to deliver affordable clothing and consistent sizes to a long-ignored market. A big & tall men’s clothing company, made by big men for big men, forged from years of frustration with what the fashion industry has to offer guys like us. A small-batch manufacturer producing a new collection every month from their facility in Lima, Peru. A responsible corporate player, empowering their customers through body positivity and self-confidence, while empowering their team members in Peru through training, mentorship and opportunities.