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 items, 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 2XL to 6XLT, our waist sizes are 40 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 partner factories worldwide, 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 or a limited edition collection or garment.

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. Not only do we offer free size exchanges, but you can also return your full order for a refund. Also, we offer a VIP service that allows you to exchange ANY item for ANY reason!


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 all active subscribers who reside in the United States!

How do I do a Size Exchange?

Just drop us a line at exchanges@thewinstonbox.com 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 and handle the shipping. If you are an active subscriber living outside of the United States, please contact us for return instructions. International subscribers are responsible for return shipping costs.

For our standard subscriptions, replacement items will be shipped out with your next order.

VIP subscribers will have their replacement items shipped out within 3-5 business days from the date we receive the returned items at our warehouse.

Exchanges should be unworn, unwashed and undamaged, with all tags still attached and in the original packaging. Due to inventory, we may occasionally need to swap out the item with an item of comparable value.

Active subscribers who return an item for an exchange and subsequently cancel their membership, and are not scheduled to receive a box, will pay a nominal shipping fee to have the replacement item shipped out.

Inactive subscribers may still exchange items with in the 15 day exchange window but are responsible for shipping costs to and from the warehouse. Once we get the item back, we contact you to make arrangements for return shipping.

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.

For our standard subscriptions, 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.

VIP subscribers can exchange any item for any reason at all.

Exchanges can be requested at exchanges@thewinstonbox.com

Can I return the whole box?

We are one of the few all-inclusive subscription boxes that offer returns. You have 15 days to request a return of your full order by emailing returns@thewinstonbox.com.


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.

Bi-monthly and quarterly subscribers will have a renewal date of the 5th of either the 2nd or 3rd month after their subscription.

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 info@thewinstonbox.com.

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 info@thewinstonbox.com and our team will push your payment out one month.