Men's Leather Chelsea Boots - Black
Men's Leather Chelsea Boots
Men's Leather Chelsea Boots
Men's Leather Chelsea Boots
Men's Leather Chelsea Boots - Black
Men's Leather Chelsea Boots - Red

Anders | Men's Leather Chelsea Boots

Regular price $159.95 Sale price$94.95 Save 41%
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These men's black leather ankle boots bring chelsea styling to a hard-working winter wardrobe.

The Anders is built for the kind of man who wants one pair of boots that does everything: office on Monday, a walk with the dog on Saturday, dinner out without a second thought. The leather upper wears in rather than out, taking on its own character with every season, while the slip-on construction means there is no fussing with laces on a cold morning when your hands would rather stay in your pockets.

Why You'll Love It

  • Leather upper: a material that holds its shape and only looks better with wear, instead of showing its age the way cheaper uppers do.
  • Slip-on ease: step in and go, no bending, no laces, no fuss on a busy morning or a cold one.
  • Ankle height with a chelsea line: sits cleanly under a trouser hem, smart enough for a jacket and easygoing enough for a weekend coat.

Perfect For

Wear the Anders with dark denim and a wool jacket for a weekend in the neighbourhood, or under tailored trousers when the day calls for something a little more put-together. Because the colour is a true black, it pairs easily with navy, charcoal and camel without a second thought about matching. As the weather turns colder, this is the boot that goes from the car to the office to the front hall without ever feeling out of place.

Frequently Asked Questions

How does the Anders fit?
It has a slip-on construction through the ankle, designed to be pulled on with ease for a full day of wear.

What should I wear it with?
The black leather makes this a genuinely easy match: dark trousers, denim, or a wool coat will all sit well with it, and it moves easily from daytime errands to a dinner reservation.

Is black the right choice for everyday wear?
Black leather is the most versatile option in a boot like this one, working with nearly every colour already in a man's closet and hiding the marks of daily wear far better than a lighter shade.

Size (US) Size (EU) Foot length
6.5 39 9.6″
24.5 cm
7 40 9.8″
25 cm
8 41 10″
25.5 cm
9 42 10.2″
26 cm
10 43 10.4″
26.5 cm
10.5 44 10.6″
27 cm
11 45 10.8″
27.5 cm
12 46 11″
28 cm
13 47 11.2″
28.4 cm
14 48 11.5″
29.1 cm
15 49 11.7″
29.8 cm
16 50 12″
30.4 cm
17 51 12.2″
31.1 cm
18 52 12.5″
31.8 cm

Unsure between two sizes? Choose the larger one for the best comfort and fit.

Once your payment is confirmed, we get straight to work preparing your order.

As soon as your order is on its way we send you a confirmation email with a tracking number, so you can follow it the whole way. You can also check in any time on our Track Your Order page.

We want you to love what you receive — but if something doesn't feel quite right, we've got you 100% covered. Whether it's the fit, the style, or anything in between, you have 30 days to return your order.

We believe clothing should make you feel like the best version of yourself — comfortable, confident and completely you. That is what drives everything we do at Evelyn & Olivia.

Finding the right piece can make all the difference, and we are here to help you every step of the way. Whether you need advice on sizing, a recommendation, or just want to say hello, we are always happy to help.

Write to us any time at info@evelynandolivia-toronto.com. We answer most messages within one business day, Monday to Friday.

30-DAY MONEY-BACK GUARANTEE

We love our products and are confident that you will too! That’s why we offer a 30-day money-back guarantee. If the product doesn’t meet your expectations, simply return it for a refund.

FAQs

Yes — shipping is free on every order within Canada, with no minimum. The price you see at checkout is the total you pay: no delivery charge, and nothing to pay on arrival.

As soon as your parcel leaves the warehouse, we email you a dispatch confirmation with your tracking link. The first carrier scan can take 24 to 48 hours to appear, which is normal. Our Track Your Order page explains how to follow your parcel and what to do if the tracking stops updating.

The size selector on each product page shows the sizes we carry, and the description tells you how the piece is cut and how it is meant to sit. If you are between two sizes, email us with your usual size and the item you are looking at — we will tell you which one we would send. That is quicker than guessing, and it saves you a return.

You can pay safely and securely with:

  • Visa
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Payment is handled securely by our payment provider — we never see or store your card details.

Free shipping across Canada

Enjoy free premium shipping on all orders. Fast, reliable, and with no hidden fees.

30-Day Money-Back Guarantee

Shop with confidence. If it’s not the right fit, our hassle-free returns make it simple to send it back.

Secure Payment

Every payment is processed over an encrypted connection by our payment provider. We never see or store your card details.

we're here for you

Have a question? Need sizing help? Just want to say hi? Reach out anytime at info@evelynandolivia-toronto.com. We personally handle every message with care.