The Winston Box - hero background

Confidence in Every Box

Premium big & tall style delivered right to your door.

Get Started How It Works

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
Get Started

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.

TAKE MY QUIZ

SAMPLE BOXES

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