4 Types of Boots to Wear With Jeans This Fall

Fall is finally here, and I’m ready to bring on the boots! There are so many great styles to choose from this season—and just as many (if not more!) trending jean silhouettes. It can all feel a bit overwhelming. But have no fear!Similar to my recent post on how to style jeans and loafers, today we’re walking through all the best boot styling options. I’ll share easy tips for pairing your favorite denim with the right footwear, how to choose outfits that complement each other, and examples of the best boots to wear with jeans this season. Let’s dive in!

Tips on Styling Boots with Jeans

Before running through specific examples of which boots to wear with jeans, I wanted to share a few general styling tips and tricks. From my experience, these guidelines are helpful every fall and winter—no matter what the current trends may be.

1. Always Try On the Styles

When it comes to boots and jeans, I’m a firm believer that you need to physically try on the combinations. Two pieces might look great side by side or even on someone else, but you won’t know if they truly work for you until you’ve tested them together. A little experimentation goes a long way!

2. Play with Proportions

Finding the right proportions and styles that complement each other is key. When pairing jeans and boots, pay attention to the length, cut, and width of the denim—especially from the knee down—to ensure they work well together. In general, you don’t want your jeans to touch the ground. Instead, opt for cuts and boot heights that let the denim lightly graze the toe box of the boot or show a little ankle. Unless, of course, you’re styling skinny jeans—which I’ll cover a little further down!

3. Select Styles That Are Going to the Same Party

This saying is a little joke of mine, but it’s true—the boot and denim you’re wearing should feel appropriate for the same occasion. I don’t love pairing overly slick, dressy boots with casual denim, and I typically avoid wearing a casual boot with a more tailored pair of jeans. There are times I like to create a juxtaposition (like pairing dresses with sneakers), but a denim-and-boot combination usually isn’t one of them!

4. Stay in the Same Color Family

When deciding which boots to wear with jeans, be sure to envision the entire outfit—including your accessories. While I love experimenting with color (and there are so many beautiful hues to wear this fall), I usually try to stay within the same color family when styling boots. That often means avoiding mixing brown and black—though I do combine these in other outfit formulas!

For example, when I’m styling brown boots, I think about my tan and brown purses and whether I have a matching belt to complete the look. The same goes for black denim.

4 Types of Boots to Wear With Jeans

Now let’s chat about some actual denim-and-boot combos I’m loving this season! I’ll break it down by boot style—booties, riding boots, lug soles, and stilettos—and highlight a few different jean cuts that pair well with each.

Booties

The bootie is a great style to start with. With a lower, tighter shaft, this boot can be styled in so many ways—making it one of the easiest types of boots to wear with jeans.

My personal favorite way to style booties is with cropped kick-flare denim. This combo creates a really pretty shape by showing the smaller part of your ankle. For example, this pair or this one would look great with cropped jeans. I also love the look of a sleek black bootie styled with black denim. You can see how I styled booties with kick flares last year here.

Wondering how to style wide-leg jeans? Try pairing a pointed-toe bootie with your favorite wide-leg to balance the silhouette. More of a straight-leg girlie? Chic booties look great with a comfortable straight-leg jean. Above I am wearing Veronica Beard booties (sold out similar here and here) with these straight leg jeans and this fun jacket. There are so many great ways to style this type of shoe!

Riding Boots

Okay, controversial take—but I’ll never get rid of my favorite skinny jeans. Gen Z can call them cheugy, but riding boots are the perfect example of why you should keep them around. Plus, you know they’ll come back in style—everything always does!

I’m loving the current equestrian trend, and one of my favorite ways to wear it is by pairing riding boots with skinny jeans, a turtleneck or button-down, and a tailored blazer. You can tuck straight-leg denim into riding boots, but that look just isn’t for me—I prefer a cleaner, tighter silhouette.

If you’re searching for new riding-boot options, I love these, these, these, and these! And if you want my look above I am wearing this blazer, with old Banana Republic riding boots (seen here) and my very old Current/Elliott skinny jeans.

Lug Sole Boots

The lug sole is one of the trendier types of boots to wear with jeans. I know this style isn’t for everyone, but it’s been growing on me this season. This is another reason it’s so important to actually try styles on and play around with them—you never know what might surprise you!

Lug-sole boots look great with cropped wide-leg jeans and flare jeans. I’ve been eyeing these boots, these, and these. Pair them with an oversized fisherman sweater for a cozy, cool fall outfit. P.S. You can check out my full guide to fisherman sweaters for even more outfit ideas!

Stiletto Boots

Stilettos are one of the trickier boots to wear with jeans. Because they have a higher shaft, you’ll want to ensure there’s enough room from the knee down for the boot to fit comfortably. Otherwise, you’ll need to commit to a skinny jean.

Personally, I like to save my skinny jeans for riding boots—not stilettos. Instead, I prefer pairing this style with wide-leg jeans or a mini skirt. I won’t go into the mini skirt styling in detail today, but I love the proportions created by a tall boot and a shorter hemline.

When styling stilettos with wide-leg denim, make sure your jeans don’t drag on the ground. Ideally, the hem should graze the top of the boot’s toe box for a clean, tailored look. These wide-leg jeans and these would both work well as long as they’re tailored to the right length. Some of my current favorite stiletto boots include these and these!

Final Thoughts on Boots to Wear With Jeans

As cool weather approaches, I hope these tips and examples of boots to wear with jeans help you create easy, polished outfits for fall and winter. Whether you’re dressing up for a night out or keeping it casual for everyday errands, the right denim-and-boot combo can pull your entire look together.Remember, fashion should always feel fun and effortless—so play around with different combinations until you find your favorites! And if you’re building your fall wardrobe, you might also love my posts on how to style a fisherman sweater, loafers and jeans outfits, and colors to wear this fall.