The sizes you need. The styles you want. Handpicked for you. Delivered to your door.



It takes less than 60 seconds! Give us your preferred sizes, styles and colors. We’ll give you a welcome call once you’ve placed your order to answer any questions you have.


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


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.

Plaid Button Down
Oxford Shorts
Print Tee
Total Box Price

You Pay Just

plus shipping (add tax in CA)

Camo Scoop Tee
Jersey Henley
Total Box Price

You Pay Just


plus shipping (add tax in CA)

DryTec Slacks
Check Button Down
Shirt Jacket
Total Box Price

You Pay Just


plus shipping (add tax in CA)

Zipper Jogger
Short Sleeve Hoodie
Print Tee
Total Box Price

You Pay Just


plus shipping (add tax in CA)


We started this company because the fashion industry forgot about us. Boring looks. Limited selections. Inconsistent sizing. We know why you hate shopping for clothes, because we’ve been there too. Every box we ship is designed with your specific needs in mind and we make every effort to keep our sizing consistent.

Read Our Story


Producing our own signature collection allows us to cut out the middleman and pass the savings on to our members. Which is why we can offer premium fabrics like Peruvian Pima cotton and stretch denim, sometimes from the same textile mills as the big designer fashion houses, for a fraction of what speciality stores will charge.

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Garment manufacturing consumes water, which is why a portion of each box funds the installation of fog catching equipment in the Peruvian desert. Each year, we help pull up to 1.7 million liters of water out of thin air and into the homes and farms of the nearly 7 million Peruvians without access to water.

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Terry P.

The Winston Box is a wonderful name, but every month when my box arrives I have a different phrase. Christmas every month! I’ve been a member for over a year. Almost every day I wear something from their line. The items range from dress shirts and pants to jeans, shorts and sleeveless tees. The Winston Box actually replaced my need to order clothes online or visit the big and tall stores.

Clifton C.

One of the biggest values I find in The Winston Box is that it takes ME out of the equation.

Historically, I haven’t made good decisions when it comes to buying clothes. I gravitate toward black and baggy and gym shorts.

Since subscribing, I’m more confident in my everyday life when I’m wearing these pieces because I have clothes that fit well and look amazing!

David C.

Great company with great owners. The products are original and very high quality and the customer service is exceptional. I receive compliments on the clothing all the time. I also received a call from one of the owners checking in to see how they were doing and asking questions about items I would be interested in for the future.

Andretti D.

The Winston Box makes being a big guy sexy and affordable. Getting amazing quality and style at our size is very hard to find. But The Winston Box makes it easy to have style and confidence that’s awesome for any guy of size!

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What is The Winston Box?

The Winston Box is a monthly subscription service catering exclusively to the plus size, or big and tall man. Every month we send a box of 2-3 items right to your doorstep based on the size, style and color preferences you provide.

No more trips to overpriced big and tall specialty stores. No more walks of shame from department stores that refuse to carry your size. Just quality clothes at an affordable price.

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.

Do I get to keep everything you send me?

Yes! This isn’t a clothing rental service… we actually think that’s kinda gross. Everything in the box is yours to keep and there are no extra charges for the clothes. Our service is all-inclusive.

What is the cost?

Big and tall guys know that some specialty stores charge you more than $75 for just a shirt. Which is why our boxes are such a great deal! You get 2-3 items in your box for just $75 (plus shipping) while saving anywhere between 35% and 70% off the total retail price. That’s a price that can’t be beat!

What sizes do you carry?

We ONLY carry big & tall sizes! Our top sizes are 1XL to 6XLT, our waist sizes are 38 to 64, and we have inseams up to 38”

What brands do you carry?

The reason most subscription services aren’t able to do big and tall sizes is that there are not enough brands making larger sizes at an affordable price. This is why we carry our own label. Nearly every item we send is designed and manufactured at our own factory in Lima, Peru, which also allows us to be more consistent with sizing than selecting from different brands.

Also, on occasion we partner with select manufacturers for accessories.

Where do you ship to?

Big men are all over the world. So are we! If you don’t see your country in our drop down list, just e-mail us and we’ll make sure to add it. Just remember, shipments outside of the United States may be subject to local duties and taxes.

We also ship to APO, FPO and P.O. Box addresses.


When do you charge me for my first box?

The first month’s membership fee is charged right after you press Submit Order on the Secure Checkout page. This order cannot be cancelled, but once you have received your box you have a few exchange and return options.

When does my first box ship?

You can typically allow up to 7 business days for the first box to ship, but we typically average between 2-3 business days. Just keep checking your e-mail for your tracking information!

I want to try your service but what if I don’t like what I get in the first box? Am I stuck with it?

That’s a great question. While our exchange policy is only for sizing, we ALWAYS make an exception on the first box or two since you are still getting used to our style categories and we are still getting to know what you want. If that first box doesn’t make sense to you, drop us a line at We’ll see what we can do to get you into something you want to wear.


I love what I got but I need a different size. Can I exchange?

Absolutely! We don’t want you wearing something that doesn’t fit which is why we give you 15 days to exchange any item for another size. Best of all, our Size Exchange Program is free for active subscribers!

How do I do a Size Exchange?

Just drop us a line at and let us know which item you want to exchange and what size you need.

If you are an active subscriber, we’ll send you a return label. Once we get the item back, we will send you a replacement in your next box.

If you are an inactive subscriber, we’ll send you instructions on how to send the item back to us. Once we get the item back, we contact you to make arrangements for return shipping.

Ship it back to us and we’ll send you a replacement item in your next box. Just make sure the tags are still attached and include the original packaging.

I don’t like what I got. Can I exchange it?

One of the unique aspects of an all-inclusive subscription service is that you’re essentially sending yourself a mystery gift each month. Sometimes you’ll end up with some items you don’t love.

Our free exchange policy is for fit and sizing. It’s not because we don’t want to have good customer service for our members. It’s just this is how the all-inclusive subscription business model works in order to keep prices low and remain competitive.

However, we may be willing to find a solution on a case by case basis. Feel free to e-mail us at

Can I return the whole box?

We are one of the few all-inclusive subscription boxes that offer returns.


When does my subscription renew?

Like most subscription services, we have standard monthly renewal dates.

If you signed up on or before the 20th of the month, your renewal date is the 5th of the following month.

If you signed up on or after the 21st of the month, your renewal date is the 12th of the following month.

When do renewal orders ship?

Our shipment arrives from our factory between the 13th and 18th of each month. We then need to unpack, sort, and take inventory on that month’s collection. Once we do that, we can start picking and packing individual orders.

Your box will ship between the 19th and 26th of each month.


When can I cancel my subscription?

We believe long term commitments are for relationships, not boxes of clothes. Once your first box has been delivered you can cancel at any time.

How do I cancel my subscription?

We’re sad to see you go. Is there anything we can do to help? We’d love it if you gave us a chance to see if we can help by messaging us at

If you still want to cancel, that’s OK. We won’t make you jump through hoops. All you need to do is log on to your account, click the big CANCEL button located in the My Subscriptions section, and that’s it! Just make sure to cancel before the renewal date listed on your account.

I need to take a month off. Can I pause my subscription?

We get it. The bills always come first. That’s why we will gladly pause your account and give you a bit of breathing room. Just drop us a line at and our team will push your payment out one month.