The Winston Box Hero

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

Step 1

SIZING

The Struggle: Finding clothes that fit as they should.

Our Fix: Sizes up to 6XLT, waists to 64”, and inseams to 38” — built for real Big & Tall bodies, not “one size kinda fits all.”

Step 2

SELECTION

The Struggle: Big & Tall style that’s… boring.

Our Fix: From off-duty looks to office-ready gear, we bring you fresh, on-trend styles for every occasion with no compromises.

Step 3

SAVINGS

The Struggle: Paying extra just because you’re bigger.

Our Fix: Pay one simple all-inclusive price. Save 50–80% off retail. Great style, at a fair price… no size tax.

Our Signature Box

$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

1. Take a 60 Second Quiz

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

Step 2

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

3. Delivered to Your Door

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

SAMPLE BOXES

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