★★★★★
4.7 / 5 Based on 1200+ Reviews

Bruce | Chukka Boots

$130.00 $79.95 SAVE 38%
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  • Icon Free Shipping with UPS
  • Icon 30-Day Money Back Guarantee
  • Icon Loved for the comfort, kept for the style
  • Low in stock. Only left.
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Ships by Tue, Jul 30
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35 YEAR ANNIVERSARY EXTRA DISCOUNTS:

  • Buy 2 → Save 10% Extra
  • Buy 3 → Save 15% Extra
  • Buy 4 → Save 20% Extra
  • Buy 5 → Save 25% Extra

Stock selling fast: BUT STILL AVAILABLE IF YOU CAN ADD TO CART

Classic style. Modern comfort. Built to last.

Step confidently through every season in the Bruce Chukka Boots — a timeless essential crafted for men who appreciate enduring quality and easy versatility. With its sleek high-ankle silhouette and thoughtfully cushioned interior, this pair delivers all-day comfort you can count on, whether you’re heading out for a relaxed afternoon or a more refined occasion.

Why you'll love this:

  • Classic chukka design with a smooth, high-ankle profile for a smart, polished look

  • Minimal lace-up front adds a touch of refinement without fuss

  • Cushioned interior supports lasting comfort, even on long days

  • Durable, traction-ready sole ensures steady footing and confidence in every step

  • Designed to pair effortlessly with jeans, chinos, or casual trousers for year-round wear

Timeless craftsmanship and dependable comfort — this is a wardrobe staple you’ll reach for day after day. Order now while your size is still available.

We are offering free shipping within the United States for all orders.

We ship our packages with a Track & Trace code so you can always monitor your order.

You will receive the Track & Trace code via email within 24-72 hours after placing your order.

If our product does not meet your expectations, you can return it within 30 days upon receipt.

Before returning the goods, please contact our customer service at info@anna-newyork.com  and let us know the reason for the return so we can process your request correctly.

Please review our return policy for more information!

Our customer service is available 24/7 to answer all your questions and comments. Whether you need advice on a product or help with an order, we are here to support you.

Don’t hesitate to contact us; we’re happy to help!

Please contact us at info@anna-newyork.com

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18 products

Customers love Anna New York

from 1355 reviews ✅

Michael Turner
★★★★★

I was a bit unsure when ordering, but these shorts turned out better than expected. They fit well, feel light, and I’ve already worn them a couple of times. Pretty solid for the price.

Michael Turner
Tracy Goodwin
★★★★★

I was a little worried about ordering clothes online at my age but the size guide was spot on. Very happy with the fit. 🤎

Tracy Goodwin
Marianne Briggs
★★★★★

This is the kind of piece you end up reaching for again and again. Just easy to wear.

Marianne Briggs
Tina Pruitt
★★★★★

First time ordering and very impressed. It felt personal and easy.

Tina Pruitt
Denise Lawson
★★★★★

Finally something that feels like it was made for women my age. Thank you for that.

Denise Lawson
Theresa Vaughn
★★★★★

My daughter said it makes me look “fresh”, I will take that any day!

Theresa Vaughn
Evelyn Rhodes
★★★★★

Was hesitant at first because I hadn’t heard of the brand, but now I’m glad I gave it a chance. I’ll be back.

Evelyn Rhodes
Wendy Monroe
★★★★★

I am in my late 60s and do not like anything too tight. This has just the right shape without clinging.

Wendy Monroe

35 years of passion

Anna New York began in 1990 with one simple goal: to help our customers feel good in what they wear.

35 years later, we’re still here, dressing our customers across the country with comfort and timeless style. To celebrate, we’re offering our biggest sale yet, up to 80% off our most loved pieces.

It’s our way of saying thank you, for every note, every photo, every order.

With love ❤️
Anna

FREE SHIPPING with UPS

Enjoy free shipping across the U.S. on us, today only! Find something you love, and we will cover the shipping. Every order ships free, straight to your door.

30-Day Money Back Guarantee

At Anna New York, we believe in your satisfaction. Enjoy our 30-day return policy for peace of mind!

Loved for the comfort

Timeless comfort, made to move with you.
Feel relaxed, confident, and beautifully at ease in every piece.