4 Essential Ankle Boots to Get You Through the Winter

Rachel Off Duty: 4 Winter Ankle Boots - Chunky Heel Bootie

These boots are c/o Thursdays. All thoughts, opinions, and styling are my own.

I think we can all agree that a good boot never goes out of style. There’s something about my coziest socks and a comfortable pair of boots that makes me feel more pulled together and seasonal, even if the rest of my outfit is pretty much what I wear year-round (I do live in Los Angeles, after all). While you’re probably currently obsessing over the revival of knee-high slouch boots, as we’re seeing them all over social media and storefronts these days it feels like, I’m here to make a case in the opposite direction. That’s right, I’m vouching for the ankle boot (or, bootie, if you like calling them that)! While knee-high boots are having their moment, ankle boots are confidently holding their own, and they’re not going anywhere. I love ankle boots for a number of reasons. First, they’re practical if you live in climates where it gets brisk, but not frigid. Second, I prefer ankle boots over anything higher when I’m going to work or to an event that requires me to sit for long periods of time – who else thinks crossing your legs wearing knee-high boots is a pain?? And last, you can take them so many ways! Knee-high and OTK boots are statement pieces, and when worn, will commandeer any outfit no matter how casual. Ankle boots, on the other hand, can be played up or played down – the star, or the supporting actress. Not to mention, I find them much comfier.

Here, I’m sharing 4 essential ankle boot shapes to get you in the mood for winter! Year after year, these 4 classic styles take me from day to night no matter the weather, and their versatility can’t be beat.

My Picks: 4 Essential Ankle Boots To Get You Through the Winter

1. Lace-Up Ankle Boots

Rachel Off Duty: 4 Ankle Boots for Winter - Lace-Up Boots
Rachel Off Duty: 4 Ankle Boots for Winter - Lace-Up Boots
Rachel Off Duty: 4 Ankle Boots for Winter - Lace-Up Boots
Rachel Off Duty: 4 Ankle Boots for Winter - Lace-Up Boots
Rachel Off Duty: 4 Ankle Boots for Winter - Winter Outfit

Casual, familiar, and a bit grungy, the lace-up ankle boot is much more versatile than some people give it credit for. Here, I played up the masculinity of the boot slightly with a gingham collared shirt and a newsboy cap. Another way I love styling these boots is with a mini skirt, sweater, or denim jacket – the perfect recipe for a great casual, flirty, look.

2. Chelsea Ankle Boots

Rachel Off Duty: 4 Ankle Boots for Winter - Chelsea Boots
Rachel Off Duty: 4 Ankle Boots for Winter - Chelsea Boots
Rachel Off Duty: 4 Ankle Boots for Winter - Chelsea Boots
Rachel Off Duty: 4 Ankle Boots for Winter - Chelsea Boots
Rachel Off Duty: 4 Ankle Boots for Winter - Chelsea Boots

Chelsea boots resurged with full-force over the last few years. These shoes are by far my favorite ankle boot shape there is. Sophisticated yet subtle, you’d be hard-pressed to find an outfit that a Chelsea boot doesn’t enhance. Tell me: in what other shoe world could a pair of plaid trousers, a lingerie-inspired top, and a moody lip look anywhere near as edgy? Go on, I’ll wait till you think of something, but we’ll be here a while.

3. Chunky Heel Ankle Boots

9E3A5151.jpg
Rachel Off Duty: 4 Winter Ankle Boots - Chunky Heel Bootie
Rachel Off Duty: 4 Winter Ankle Boots - Chunky Heel Bootie
Rachel Off Duty: 4 Winter Ankle Boots - Chunky Heel Bootie
Rachel Off Duty: 4 Winter Ankle Boots - Chunky Heel Bootie

I had a not-so-quiet obsession with high-heeled ankle boots when I moved to California. I bought 6 pairs within my first year. That love affair quadrupled when I studied abroad in Italy, as chunky heeled boots were the safest match for cobblestoned streets and freezing temps. There’s really no other way to slice it – chunky heel ankle boots are the most practical and comfortable way to elevate your look (literally) without compromising your ability to walk. I love this bold, red pair and was drawn to the plaid movement we’ve been seeing lately, which was the inspiration behind this outfit.

4. Pointed Toe Ankle Boots

Rachel Off Duty: 4 Ankle Boots for Winter - Pointed Toe Ankle Boots
Rachel Off Duty: 4 Ankle Boots for Winter - Pointed Toe Ankle Boots
Rachel Off Duty: 4 Ankle Boots for Winter - Pointed Toe Ankle Boots
Rachel Off Duty: 4 Ankle Boots for Winter - Pointed Toe Ankle Boots
Rachel Off Duty: 4 Ankle Boots for Winter - Pointed Toe Ankle Boots


Last but not least, there’s nothing like a pointed toe. The beautiful thing about pointed toe boots is that for whatever reason, if you have a pointed toe, nothing else matters, because you’ve already achieved instant sophistication. This signature shape screams edginess and class in a way that no other boot shape can. In keeping with the idea of sleekness with an edge, I went for a head-to-toe monochrome look.

More Ankle Boots:

What pair are you most looking forward to wearing this winter?  

More Style: