Leander | Men's Insulated Slip-On Ankle Winter Boots
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These insulated slip-on winter boots keep men's feet warm through the coldest days.
The Desmond is built for the season when mornings turn frosty and the walk to the car or the mailbox calls for something reliable underfoot. A padded quilted upper, a soft fleece collar and an insulated lining work together to keep the cold out, while the slip-on fit means there's nothing to lace, buckle or fuss with on a rushed morning. These are the kind of boots you reach for without a second thought once winter sets in.
Why You'll Love It
- Insulated Warmth: the fleece collar and insulated lining keep ankles comfortable even on raw, biting days
- Slip-On Ease: no laces or fiddly fastenings, so getting out the door is quick and simple
- Supportive Sole: a chunky, grounded sole gives steady footing on icy pavement and packed snow
- Quilted Detailing: the quilted pattern across the upper adds a bit of texture and visual interest beyond a plain boot
Perfect For
The Desmond suits daily winter wear: a walk around the neighbourhood, errands downtown, or simply keeping warm while clearing the driveway. The rounded toe and ribbed panelling give a practical, everyday shape that pairs easily with jeans, trousers or casual winter layers, and the quilted finish looks tidy whether you're heading out for the morning paper or an afternoon coffee with friends. It's a boot built to be worn often, not saved for best. Because they slip on and off so easily, they're also handy for quick trips outside, like grabbing the mail or taking the dog out, when you don't want to deal with laces.
Fit: These ankle boots sit true to size with an easy slip-on fit, so there's room for a warm sock without feeling snug. If you're between sizes, most men find their usual size comfortable here.
Colour: Black is the most versatile choice and works with almost anything in a winter wardrobe, while Blue and Red offer a bit more personality for those who like a change from classic black.
Styling: Keep it simple and let the boot do the work — these pair naturally with everyday trousers, warm trousers or denim, and sit well under a longer winter coat for a tidy, put-together look on cold days. A pair of thick wool socks rounds out the look while adding another layer of warmth on the coldest days.
| 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.
