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Men’s Side Zip Chelsea Ankle Boots
  • Men’s Side Zip Chelsea Ankle Boots
  • Men’s Side Zip Chelsea Ankle Boots
  • Men’s Side Zip Chelsea Ankle Boots
  • Men’s Side Zip Chelsea Ankle Boots
  • Men’s Side Zip Chelsea Ankle Boots
  • Men’s Side Zip Chelsea Ankle Boots
  • Men’s Side Zip Chelsea Ankle Boots
  • Men’s Side Zip Chelsea Ankle Boots
  • Men’s Side Zip Chelsea Ankle Boots
  • Men’s Side Zip Chelsea Ankle Boots
Men’s Side Zip Chelsea Ankle Boots

Autumn Collection

Men’s Side Zip Chelsea Ankle Boots

BESTSELLER
  • Soft lining to keep your feet cosy
  • Easy to slip on — no laces to tie
  • Slip-resistant soles for added grip
$209.90$104.95
COLORBlack
SIZEUS 7 - EU 38
Selling fast - If you can click "𝗔𝗱𝗱 𝗧𝗼 𝗖𝗮𝗿𝘁", it's still available!
30-Day Easy ReturnSecure Checkout

Mix & Match — More to Love, More to Save

Buy 2Get 10% OFF
MOST POPULARBuy 3Get 15% OFF
Buy 4Get 20% OFF

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Shipped by Mon 5 Oct
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WHY YOU'LL LOVE IT
Easy to Style

Pairs effortlessly with the pieces you already own.

Comfortable Fit

Designed to feel good from morning to night.

Made for Everyday

Versatile enough for work, errands and weekends.

Shop with Confidence

30-day easy returns and free shipping across Canada.

PRODUCT DETAILS

Still Searching For Smart Shoes That Stay Comfortable All Day?

Too many pairs feel stiff, rub during the commute, or leave you second-guessing your outfit by midday. Choose this pair and stop compromising—supportive cushioning and balanced structure help you move with ease from first step to last. From office hours and client dinners to weekend plans and city strolls, it fits seamlessly into your routine. You feel confident, put together, and ready for the day.

What Makes This A Confident Choice For Work, Weekends, And Events?

• Balanced Cushioning For All-Day Ease: Keeps your steps comfortable through meetings, commutes, and evenings without distracting fatigue.
• Sleek Profile That Elevates Outfits: Pairs seamlessly with suits, chinos, and jeans so dressing smart never feels complicated.
• Stable Traction You Can Rely On: Helps you walk confidently on busy days, city pavements, and airport terminals.
• Neat Finish That Stays Presentable: Maintains a clean appearance from the first meeting to the last errand, even with frequent movement.
• Effortless Go-To When Getting Dressed: A simple, reliable choice that streamlines your routine and makes confident outfits easy, day after day.
SHIPPING & RETURNS

Free shipping on all orders with Canada Post.

Please allow us the following shipping times:
Expected delivery: 6-13 days

Easy returns
All products can easily be returned within 30 days. Returns are refunded to the original payment method. Products must be returned unworn, unwashed, in their original condition and with all tags and liners attached.

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Our Story

From Milan to Toronto, a dream we built together.

We first met in high school in Toronto, but life took us in different directions. Years later, by pure coincidence, we found each other again while travelling in Milan, Italy. Inspired by the city, its people and its effortless sense of style, we returned home together, with a love for fashion that never left us.

A Dream We Never Forgot

Ten years ago, we took a leap of faith, left our careers behind and opened Connor & Claire in Toronto. Our vision has remained simple ever since: stylish, timeless clothing for men and women, combining quality, comfort and elegance at a fair price.

A Little Treat, From Us to You 🎃

As autumn settles over Toronto and pumpkins light up the neighbourhood, we’re celebrating the season with a little treat of our own.

This week, enjoy up to 70% off selected styles in our Halloween Sale. Whether you’re finding a cosy new favourite or choosing something special for someone you love, we hope you discover a piece that becomes part of your story.

Thank you for being part of ours.

With love,

Connor & Claire ♡

Over 2,847+ Happy Customers

Olivia M.

Olivia M.

Verified Buyer 🇨🇦
2 hours ago

“The fit was exactly what I was hoping for, comfortable without looking oversized. I’ve already received several compliments.”

Katy O.

Katy O.

Verified Buyer 🇨🇦
8 hour ago

“Ordering was easy, and the tracking link worked perfectly! Everything went smoothly, and my order arrived in lovely packaging for their 10th anniversary sale last month.”

Emma T.

Emma T.

Verified Buyer 🇺🇸
Yesterday

“A really flattering piece and very easy to style. I wore it to dinner with jeans and boots and felt put together without being overdressed.”

Maeve S.

Maeve S.

Verified Buyer 🇨🇦
2 days ago

“I’m always a little hesitant ordering clothes online, but the sizing was very accurate. The fabric feels soft and it looks just as nice in person as it did online.”

Charlotte B.

Charlotte B.

Verified Buyer 🇺🇸
3 days ago

“It can be difficult to find clothing that feels stylish for my age. Connor & Claire always seem to have what I’m looking for and what feels right for me. Very pleased with my purchases as always.”

Jennifer D.

Jennifer D.

Verified Buyer 🇨🇦
1 week ago

“Delivery was straightforward and the item arrived nicely packaged. I especially like that it’s comfortable enough for everyday wear but still looks polished.”

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