The Boots That Never Go Out Of Style
Do you have the number one must-have shoe for fall and spring? It’s the ankle boot and it never goes out of style. In this easy-to-follow post, I share how to wear ankle boots with jeans, dresses, and skirts.
I recommend having a classic pair in black and a neutral pair in tan, nude or gray. To get the most out of your wardrobe, look for a classic style that you can walk in easily. Whether you love a block heel or a flat ankle boot, you want boots that will take you from day to night. Being versatile is what makes it a must-have for fall.
From wearing ankle with jeans, dresses, skirts, or leggings; I’ve styled these shoe essentials 10 different ways in the video below.
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How To Wear Ankle Boots With Jeans & Dresses
10 Ways To Style Ankle Boots Video
How To Wear Ankle Boots With Jeans & Dresses
When you’re styling dresses with ankle boots, I love to pair a cardigan to give the look a more casual daytime vibe. I love the look of wearing a dress in the fall with ankle booties and you can take this look easily into winter just by adding some opaque tights.
If you’re wearing skinny jeans with your ankle boots, it’s easy to have them tucked into your boots. This elongates your legs and is very much still in style. I like to pair something more oversized on top when I’m wearing skinny jeans or something more fitted on the bottom. So I recommend doing a half or french tuck into your jeans to bring in the waist and give your body more shape.
Another way I recommend wearing your jeans with your ankle boots is to look for a pair of denim that is a slim straight slightly cropped style. This style of jeans works really well with ankle boots because the jean goes over the top. If the jeans are longer and not fitted, then you would want to think about doing a little roll of the cuff of the jean so it sits over the ankle boots. This makes your look more stylish.
Creating More Outfits With Ankle Booties
One of the ways I like to create outfits is by pairing opposites. I love to style something like a pink cashmere sweater with a raw step hem pair of black jeans. The combination of the feminine sweater with the edginess of the raw hem denim works perfectly when styled with black ankle booties. Because of the interesting hem detail, I recommend wearing raw-hem jeans on the outside of your boots. They may look a bit messier, but I like that.
I also love wearing knit dresses with ankle boots. If the dress comes above the knee, wear a pair of thick opaque tights to keep your legs warm. But ankle boots and bare legs work great for the fall and spring. If you are fair or your hair is blonde, you may find wearing camel or tan ankle boots may work better for you instead of black. The lighter color boots will tie in together with your light hair color.
The next way I love to style ankle boots is with a pair of faux leather leggings. Leggings are a great option to wear with booties because they easily go into ankle boots. When styling your booties and leggings, wear something flowier on top.
The last way I like to wear ankle boots is with a silk midi skirt. I love the flowiness and femininity of the skirt paired with the structure of a great ankle boot. Ankle booties help to ground a look and make it feel more earthy.
In Conclusion:
When you are looking for your perfect pair of ankle boots, make sure you can walk in them easily. You really only need two pairs, in my opinion, a black and a neutral. Then you’ll be able to wear them with anything. I recommend looking for high-quality ankle boots that are classic. Avoid booties with a lot of hardware because they will tend to go out of style faster. Most importantly look (and save) for the ones that you love, and you will get a lot of use out of them.
10 Ways To Style Ankle Boots Video
FAQs & Expert Tips
Do you tuck jeans into ankle boots?
The only jeans you should tuck into ankle boots are skinny jeans. I do not recommend tucking straight or even slim leg jeans into booties. It will look sloppy. If you prefer to wear straight or slim leg denim with your ankle booties there are two ways to do that. The first is to look for a pair of jeans that are slightly cropped so that they hit just above the ankle boots. Another way to make jeans that aren’t cropped work with ankle booties is to do a messy roll so the jeans sit on top of the ankle boots.
Should you wear jeans inside or outside ankle boots?
Skinny jeans should be worn inside your ankle boots. All other styles of denim like straight leg or flare should be worn outside your booties. Either look for a pair that is cropped and hits above the boots, or do a messy cuff that rests on the top of your booties.
Related: The Style Advice I Wish I Knew 20 Years Ago
Should ankle boots be tight or loose around the ankle?
The lower your ankle boots are, the looser they can be. Ideally, ankle boots should fit tight around the ankle to create a slimming and lengthening effect for your legs. This is especially true if your booties are higher.
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