Austin | Men's Winter Leather Ankle Boots
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These men's winter leather boots pair a sturdy build with the warmth this season calls for.
The Desmond is a pair of men's leather ankle boots built for the colder months, when a reliable pair of boots matters more than almost anything else in the closet. The black leather upper is soft to the touch but holds its shape well, and the chunky rubber sole underneath gives a steady, grounded feel with every step. A side zipper sits alongside the laces, so getting them on and off doesn't turn into a production on a cold morning.
Why You'll Love It
- Leather upper: supple and breathable, it moves with the foot rather than against it, and softens further the more it's worn.
- Non-slip rubber sole: a shock-absorbing, textured sole keeps footing steady on wet pavement, icy steps or uneven ground.
- Lace-up and zip closure: laces for a secure fit through the ankle, a side zip for quick, easy on and off.
Perfect For
These are the boots for the stretch of the year when the weather can't be trusted. Wear them with raw denim and a wool sweater on a weekend walk, or under straight trousers for the commute into a cold office. The black leather is dark enough to go with almost anything already in the wardrobe, and the ankle height means they tuck neatly under a longer winter coat without any bulk showing. They hold up just as well on a gravel path as they do on a slick sidewalk, which makes them a boot worth reaching for most days through the winter.
Common questions
How does the fit run?
The leather is soft from the start and the footbed is cushioned, so there's little real break-in needed. The lace-up front lets you adjust the fit through the instep, and the side zip means you don't need to loosen the laces fully each time you take them off.
Will the black leather go with what I already wear?
Black is about as versatile as it gets. It pairs easily with navy, grey, brown and olive, and it won't fight with a patterned coat or scarf the way a lighter colour might.
What should I wear them with?
Jeans or chinos tucked loosely at the ankle work well, as do wool trousers for something smarter. A longer coat or a quilted jacket on top finishes the look nicely for the colder days ahead.
| 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.
