Inside: Style tips for how to wear booties with leggings this season! It changes every year, so get the 2023 taste.

Every year, our favorite staple pieces and trending items change just a little bit, to shift the overall aesthetic to match whatever the big thing is for the year. This doesn’t mean you have to change out your pieces each season, but changing the little ways that you style them will make a huge difference.

Leggings have been a staple for years now, an honestly good with everything kind of outfit. Recently we’ve brought back the 2000’s yoga pants as flair leggings, but this is really the only shift in the legging world.

Boots and booties however have faced major shifts, changes, and trend differences every year and we always have to find a new and edgy way to style them that will be a little more fashion forward than basic.

If you need some inspo so that you don’t feel so caught up in 2015 styles, then this post is for you!

 How To Wear Booties With Leggings 2 ideas

Even if the boots and the leggings stay the same, you’ve got a hundred ways to style them to make it fresh, new, and trendy again. Check out these styling tips and outfit inspirations to get a good idea of what you’re looking for when you start to throw on your booties with your leggings!

The Difference Between Boots And Booties

The biggest difference between boot styles when trends start to shift is whether it’s a boot or a bootie. Both are always in style and always acceptable, but some years the bootie is more hot and some years it’s a classic boot that we’re after.

So what’s the difference to look for when you’re boot shopping?

Booties are a smaller version of a boot, essentially.

They have the similar structure in the foot, the sole, and the heel, and they look like a boot, but they don’t go as high up on the leg. When booties first hit the market and were the trending shoe everywhere for the fall and winter seasons, it was any boot that stopped about the ankle.

Now, booties have a ton of variety, and something might be labeled a bootie even if it goes half way up the calf. If it’s the shorter version of a taller boot, that label still stands even if it’s a bit taller than your usual bootie style.

Boots, we all know about and what they look like. I wouldn’t even know how to define it, it’s just… a boot!

No matter the fabric the shoe is made of, the color, or the style, there is always a boot and a bootie version of it on the shoe market.

Boots on a lace backdrop

How Do These Styles Change?

The styles change based on the overall aesthetic of a trend cycle.

Some years more retro aesthetics are driving all the trends so we have more of a 60’s inspired round toe bootie, and some years we’re in more of an elevated glamor aesthetic so a pointed toe, classy boot is the vibe.

The biggest elements of a boot that change the aesthetic is the toe shape, the way it fits at the ankle, the height, and the extra designs.

Styles change all the time in shoes, jeans, tops, accessories, dresses, jackets… and it’s usually always really minimal differences that change the entire style of the item. A simple change like designing a jacket to fit even slightly oversized makes the difference between an intentionally polished look or an intentionally grunge and casual look when looking for tips for how to wear booties with leggings.

As you shop for boots and booties this year, you’ll find that you probably like some more than others and can’t put your finger on why, especially if they’re really similar.

The subtle changes in how they fit or how they’re designed make all the difference in how you’re going to style them and the general style aesthetic they’re going to lend to your look. So choose boots that are either versatile or are super specific to your target aesthetic, and it will make it so much simpler to style them how you want. It’s okay to be picky about shoes!

Mid calf black boots

Trending Bootie Styles

Currently we’re in a trend cycle that really loves both western wear and preppy attire. How the two have blended together, I don’t know but it really has translated into the shoe market especially!

Western style boots are of course huge right now, and even the short ankle cowboy boots are on fire these days. If this is your style, you will have an easy time finding some booties for you this season. There are straight up cropped cowboy boots and there are booties that are western inspired but not necessarily your classic western boot.

If you’re more on the preppy side of things like me, you’ll find that most booties that have been trending for a while are going to be pretty similar. The leather, rounded toe, with a little gold logo is very Blair Waldorf if she decided to wear booties instead of designer ballet flats or heels. The more like a short riding boot the better! The ones I still have in my closet from 2018 are perfect for the current trend cycles, but there’s an elevated version circulating right now that I can’t keep my eyes off of. It’s the same thing but a little taller, and it just looks like old money vibes, and I’m obsessed. They haven’t made it down to the consumer level of the shopping circuit yet, my favorite ones are by Chanel. But when they do, they’re mine for sure!

These are just two of the biggest bootie trends right now, but the sky’s the limit with what you can do with a good bootie and legging combo!

Leggings and booties

Booties And Leggings

Hopefully dissecting bootie trends and styles helps you gauge what your style is and how you want to personally style your own wardrobe and boots!

Styling booties with leggings can really be best explained through pictures and showing you what works. So I’ve collected some of my favorite examples of booties with leggings outfits and how you can style them to be the best representation of your own style!

1. Suede And Leather
2. Platform Boots
3. Chic Sweater
4. Grungy
5. Ugg Minis
6. Leather Jackets
7. Oversized Sweater
8. Blazer
9. Hoodie And Denim
10. Faux Leather

Wearing leggings with booties will always be the best style to reach for when the temperatures start to drop and you just need an easy go to outfit for dinner tonight. You can always have a safe bet with a sweater, leggings, and booties.

But elevating your closet and learning how to style the same pieces every year to stay fresh can be tough sometimes, but there are years and trend cycles where all it takes is a fresh new top or a little accessory to match the new vibe for the season.

And as long as it all matches your personal style, that’s all that counts anyway, and you should totally just wear what you want. I’m a big advocate for this.

If you need some new tops to shop for to go with your leggings and boots, I already have you covered. Here are 53 shirts to wear with leggings and boots that you need in your closet!

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