How to Wear Booties and Boots with Jeans

One of THE top topics our clients and followers like to chat with us about is how to wear boots and booties with jeans. We all know that there are countless styles, shaft heights, colors, and heel heights to choose from. And each one of them are unique in terms of how they pair with your denim (which incidentally is another category that features endless options to choose from). When it comes to boots and booties, the world is your oyster.

Before we dive into some detailed tips on styling your boots with denim, here is our first trick of the trade. There are certain pieces you will definitely want to have as staples in your closet: a pair each of black booties and taupe booties (you will wear this color tone far more than you think – more on that later) with an everyday heel that works for you (for some, that might mean flat, and for others, that might mean a three inch heel, depending on your preference), as well as a heeled bootie that you can dress up for date night or girls night.  

How to Wear Booties with Jeans

We think everyone should have a dressier, heeled bootie in their closet. You will reach for it time and time again – not just with denim, but with pants, skirts, and dresses too! A heeled notched bootie like this pair Katie is wearing here is one of our go-to’s for a dressier option.

The key when wearing this style of bootie with your denim is to ensure that the hem of your denim sits just above the top of the bootie. If you can achieve this without rolling, that is perfect. Otherwise, do enough small rolls to get there.  That said, don’t choose jeans that will require a thick roll to get the length right. That will detract from the sexy notch that makes this bootie so special in the first place! It is OK for the jeans to come a very small bit into the notch, but keep it to an absolute minimum so the jean isn’t competing with the whole point of the bootie!

Dressier Booties with Jeans

Katey has elevated a fairly casual look here by putting on a pair of slightly dressier booties. The heel height and shape lend these booties to both casual and dressy. A bootie like this will work overtime for you! Note the wooden heels. Such a fun edition of a special detail.

Katey has paired her booties with a classic skinny jean with a slightly tapered ankle. Because this bootie has a wider opening at its top, you can either roll your jeans to the top of the bootie or tuck your jeans into the bootie. If you choose to tuck your jeans into the bootie, make sure there is no visible bunching or puddling at the bottom. If you do experience this, roll your jean UNDER and then tuck into the bootie. Lastly, we just have to point out Katey’s mixing of color hues here!  We absolutely love that she paired a brown bootie with black denim and a grey scarf! Do not be afraid to mix these three color tones, ladies!

How to Wear Sock Booties with Jeans

We love a good sock bootie – this is a bootie featuring a higher ankle shaft fitting close to the leg. Katie has had this pair for years and has found that the combination of the style and color make for endless options! Again, don’t be afraid of wearing your taupe bootie with a dark top! When you pair your sock booties with a bit of a wider leg jean, you can allow your jeans to fall over the bootie a little bit. 

In this look, Katie is wearing the same sock booties with a distressed boyfriend jean. Love the contrast of this classic sweater and snakeskin crossbody with an edgy jean! With this particular pair of denim, Katie rolled her jeans to where the roll sits just below the top of the sock bootie. We love this look! If you choose to do this, just make sure the roll isn’t super thick or standing too wide from the bootie.

How to Wear Snakeskin Booties with Jeans

We all know that Jenny KNOWS how to mix traditional with edgy – this is how you do it right here! Love Jenny’s sweet, ruffled sweater paired with the distressed asymmetrical hem jean. And then the fun addition of pattern with these classically cut snakeskin booties just finishes the look off to perfection. Note that the jeans at their lowest point sit right at the top of the snakeskin bootie. A little skin shows in front where the hem notches up, which is spot on.

How to Wear Booties with Flare Jeans

Flare jeans have made a comeback in the last couple of years. We had all gotten so used to pairing our skinny, tapered leg jeans with our boots and booties that we had to reteach ourselves how to accessorize jeans with a wider leg! The key here is don’t overthink it! In terms of boots and booties to wear with your flares, anything that only shows the heel, a bit of the back of the bootie, and the toe goes.

In fact, it is more about getting the length of the jean right than choosing the right boot. Make sure the hem of your flare jeans sits about an inch (maybe even a little less) from the floor. This maximizes the point of this type of jean, which is to elongate those legs! It might be best to choose one or two pairs of boots to wear with this pair of jeans and cater the hem to that particular heel height. We typically recommend at least a two inch heel with this style of jean (unless you are already tall and don’t wear heels in general). Again lengthen those legs ladies!

How to Wear Combat Boots and Jeans

Combat boots. Well, what can we say?? People tend to have very strong opinions about combat boots. It’s true that back in the day, they used to be considered an “alternative” look. Many of our clients love to rock a traditional combat boot. And some of our clients don’t love an edgy look – and we get that for sure! BUT if you are on the fence on the combat boot, please know that there are SO many fabulous takes on them out there that are more classic. In fact, this has us thinking we might need to do a blog post just on combat boots…. 

Emily certainly shines in a combat boot. Whether she is going more traditional with a pretty sweater and jeans, or edgy with a graphic tee and leather jacket. We love this particular pair she is wearing here. The lace up style and lug sole are a nod to the edgier side of the trend, but the heel lends itself to a dressier look if that’s what you want to go for! There are endless ways to wear combat boots, and honestly no real rules about how to do it. It all depends on your fashion preferences! You can lace combat boots up over your skinny jeans. You can roll your jeans with a tapered ankle to the top of the boot (and maybe let your boot socks peek through). Or you can wear your distressed boyfriend jeans with your combat boots. This is one that it is best just to have fun with and know that almost anything goes!

How to Wear Over the Knee Boots with Jeans

Let’s chat one of this year’s big trends – over the knee boots! Whether you are wearing slouchy or structured over the knee boots, you will always want to wear jeans that are form fitting on the thighs. No bunching or bagginess allowed!

For those petite followers out there – just be extra cognizant of where the boot hits you on your thigh. You wouldn’t want them to come up more than about 1/3 of your thigh. Use Jenny, who is 5’2” as a point of reference.

We love so many things about the structured over the knee riding boots that Emily is wearing here. Emily has expertly paired two different shades of brown here. Her whiskey colored faux leather jacket and her chocolate brown boots are perfect together. Again, don’t overthink mixing browns! Contrary to popular opinion, you do NOT have to go matchy matchy on your color tones ladies!