9 Best Ankle Boot Outfits to Copy This Winter According to Pinterest

Budget Fashionista


Ask Google what to wear with ankle boots and you'll see an unending feed of very similar outfits. You know the look. It involves slightly distressed skinny jeans, a scarf, plus a long cardigan. Often, there's a cup of coffee and a pair of sunglasses in there, too. That outfit, or some version of it, shows up again and again across the interwebs because it's cute. But it's not the only -- or even the best -- way to wear your ankle boots.

Ankle boots are actually super versatile. Contrary to popular belief, you can wear with them with shorts, capris, midi dresses, and even pencil skirts. Here are nine amazing and interesting ankle boot outfits you can copy today.

1. An oversized fuzzy coat

The shaggy coat is currently transitioning from all-out fad to a fun style you can wear season after season. The excessively soft and textured material creates a nice contrast with the edgy lug boot. But even if you're not a combat-boot gal, you could easily swap out those clunkers for a more wearable, flat-soled boot.

You can also pull elements from this outfit to create your perfect look. Note the use of solid, neutral colors. No patterns are needed, because this is a texture play. The fuzzy coat, shiny leather boots, fringed scarf, and quilted leather bag work together in a way that no pattern can.

2. Rolled jeans and tight top

This is Emily Ratajkowski and she probably looks amazing in anything. But even so, her ankle boot game here is strong. This outfit works because her jeans aren't too tight or too loose. Too-tight skinnies fight back when you try to roll them. And rolling mom jeans never looks intentional enough, because they can't hold a decent shape. You'll either look like you're wearing fatigues and ready for combat, or like your basement flooded and you needed to keep your pants dry.

Emily has navigated the jean fit perfectly with straight-cut denim that shows off her figure. Those block-heeled boots, a simple black top, statement earrings, and an interesting belt finish the look.

3. Leggings and moto

If you're going to wear leggings as pants, do it this way. A chunky turtleneck knit that hangs just over your bum makes all the difference between trashy and chic. And topping that sweater with a moto jacket? Just brilliant. The ankle boots fall right in line with the "don't mess with me" vibe, too. Boots that are sleek and not too open at the collar will work best in this combination.

4. Wider-leg crop pant

Long and lean ladies, this outfit is for you. Pair up a wider leg cropped pant with a chunky boot and let your ankle peek through. If you go with solid, darker colors like those shown here, you will accentuate your height. If you'd prefer to be less imposing (but why?!), break up that seamless look with a top of a different color. You could even skip the trenchcoat entirely in favor of a shorter blazer.

5. With colored pants

A sleek boot can anchor your boldest colored denim or corduroy. You get bonus points for adding a massive bag and slouchie beanie to the mix. If your straight-cut pants land past your ankle, roll them neatly.

6. Midi pencil skirt and hoodie

Anyone can pair ankle boots with a flowy skirt, but it takes a true fashion gal to don ankle boots with a midi skirt and hoodie. The pencil skirt is a slim silhouette, so this combo works best with an equally slim sock boot.

Full disclosure: Some fashionistas will tell you sock boots are out of style and you shouldn't wear them. I say, who cares? Trends aren't supposed to own you. Wear the sock boot if you love it and you have an outfit that works.

7. Monochrome, with tights

You can wear ankle boots with tights, as long as the collar of the boot isn't enormous. Actually, in general, a boot that's wide at the top is harder to wear. It just looks like you're standing in twin buckets.

In this outfit, the ankle boots step in for black plumps -- a usual choice for this type of outfit. It's a chic choice that's also more practical -- since ankle boots are both warmer and easier to walk in than pumps.

8. Socks

When your pants don't quite reach the top of your boot, a cute sock can fill the void. You could also wear leggings and slip your socks on over them -- but you may have to experiment with the thickness of sock to avoid rocking the leg-warmer look. Socks can also help streamline the appearane of a boot that looks awkward because it's too wide at the top.

9. Instead of pumps

If you're at a loss for what to do with your ankle boots, try wearing them whenever you'd naturally reach for pumps. Most of the time, you'll be happy with the result. Consider what this velvet dress would look like with pumps, for example. Still pretty, but not as interesting, right? That's what ankle boots can do for you -- add interest and style.

What you shouldn't wear with ankle boots

To close, I'll leave you with a few thoughts about what doesn't work as well with ankle boots. Joggers come to mind first. You'll struggle with their length -- they don't sit right, whether you pull them over your boot or tuck them in. Baggy pants are also challenging, for the same reason. Floor-length pants aren't a great match, either. A wide-legged pant will cover up your boot and slim-leg pant will bag up around your ankle.

Beyond those pieces, nearly anything goes.

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I'm a fashion blogger and personal finance writer on a mission to spread beauty, laughter, and smarts. I love puns, cheap outfits that look expensive, people who are genuine, horses and dogs (because they're always genuine), and money. You'll mostly hear about budget fashion and beauty from me -- but once I can articulate the answer to everlasting happiness, I'll share that too.

St. Louis, MO

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