The Winston Box - hero background

Confidence in Every Box

Premium big & tall style delivered right to your door.

9+

Years in Business

1,000,000+

Garments Delivered

20

Countries Served

WHY BIG & TALL MEN LOVE THE WINSTON BOX

Why - Sizing

SIZING

The Struggle: Finding clothes that fit as they should.

Our Fix: Sizes up to 6XLT, waists to 64”, and inseams to 38”.

Why - Selection

SELECTION

The Struggle: Big & Tall style that's boring.

Our Fix: On-trend styles for every occasion with no compromises.

Why - Savings

SAVINGS

The Struggle: Paying extra because you're bigger.

Our Fix: One simple price — save 50–80% off retail.

Our Signature Box

Signature Box shot
$75
Per Box
Same Price
Since 2016

(plus tax and shipping)

  • ✔️ Monthly, bi-monthly or quarterly
  • ✔️ Receive 2-3 Items per box
  • ✔️ Minimum retail value of $150
  • ✔️ Keep everything we send
  • ✔️ Exchange what doesn't fit
  • ✔️ Return what you don't love

How It Works

Step 1 - Take quiz

1. Take a 60 Second Quiz

Tell us how often you want a box and your size, style and color preferences!

Step 2 - Stylists

2. Our Stylists Get To Work

We use your style quiz to build your first box, or you can schedule a call with our team!

Step 3 - Delivered

3. Delivered to Your Door

Fresh looks arrive monthly, bi-monthly, or quarterly — hassle-free and ready to wear.

MEMBER SPOTLIGHT

member spotlight image - Mike

A Man For All Seasons

Name
Mike
Member Since
2019
Boxes
28

Mike has been a loyal customer for seven years on a quarterly schedule because the service keeps his wardrobe feeling fresh without being overwhelming. Every three months, once a season, his box gives him a simple reset—new pieces that fit his life right now—while still letting him build a wardrobe intentionally over time. He loves that the schedule is predictable and that each delivery adds another layer to what he already owns, so his closet gets better gradually instead of all at once.

member spotlight image - Mike
member spotlight image - Roderick

The Winston Lifer

Name
Roderick
Member Since
2017
Boxes
101

Roderick is the definition of a lifer, nearly ten years strong, with a box every single month. He sticks with the service because it removes the hassle of shopping while consistently keeping his rotation updated with pieces that fit and feel right. Over the years, he’s come to trust the process: something new arrives, it works with what he already has, and his wardrobe stays current without him having to think twice.

member spotlight image - Roderick
member spotlight image - Miguel

The Urban Cowboy

Name
Miguel
Member Since
2022
Boxes
23

Miguel has been with us for four years, using the service flexibly and sometimes swinging by our Fort Worth location to pick up his box in person. His style leans country, and he likes that he doesn’t have to change who he is to shop with us—he can pull in a few well-chosen pieces that complement his boots-and-denim staples. For him, the best part is having a reliable source for big & tall options he actually wants, available when he needs them, on his terms.

member spotlight image - Miguel
member spotlight image - Brian

Healthy and Happy

Name
Brian
Member Since
2023
Boxes
19

Brian has been on a weight-loss journey for the past three years, and the service has become his go-to way to keep his closet functional as his size changes. He loves being able to refresh essentials without constantly re-shopping from scratch and that he can change how often he needs a box whenever it suits him. The size exchange option gives him confidence that things will fit him when he needs them. For Brian, it’s not just convenience—it’s a stress-free system that supports his progress step by step.

member spotlight image - Brian

SAMPLE BOXES

Sample box winter
Sample box summer
Sample box business
Sample box fall
Sample box travel
Sample box winter
Sample box summer
Sample box business
Sample box fall
Sample box travel
Sample box winter
Sample box summer
Sample box business
Sample box fall
Sample box travel

What Our Members Say

“Finally, clothes that fit me right and look amazing. The Winston Box changed how I shop.”

— James P.

“Love the variety every month. Everything fits perfectly and matches my style.”

— Marcus D.

“Top quality clothing. Feels like having a personal stylist for Big & Tall guys.”

— Robert L.

Ready to Upgrade Your Wardrobe?

Join thousands of Big & Tall men who trust The Winston Box for high-quality, perfectly fitting clothes—delivered straight to your door.

Get Started Today