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All The Best Boots to Wear with Skinny Jeans in 2021

All The Best Boots to Wear with Skinny Jeans in 2021

The best boots to wear with skinny jeans, you ask? There are so many footwear options with skinnies. And boots and skinny jeans are one of my favorite styling combos.

There a lot of shoes to wear with skinny jeans, but for the Fall season, nothing beats a good pair of boots! Being as tight as they are, skinnies pair perfectly with anything from a lower ankle boots to the higher of thigh highs. 

And there are so many trendy & classic options that no matter what type of style you prefer, one of these boots will surely strike your fancy as the boot choice to pair with your skin tight jeans!

I have many skinny jeans & I have many shoes. I’m sure you do too, so the options are rather astounding! Especially in the winters when boots are the more practical shoe option.

Below are some of my top skinny jeans with boots pairings of the moment with links below each to the best choices currently available in stores. The hottest skinny jeans styles at the moment have a mid to high waist and are ankle length. You can shop designer skinnies at Net-A-Porter and all sorts of skinny jeans and prices over at Nordstrom. Here are my fave fave picks for skinny jeans available right now:


Shop Current Skinny Jeans:


8 Fave Boots To Wear with Skinny Jeans

Skinny Jeans with Ankle Boots

ankle boots and skinny jeans

Ankle boots and skinny jeans are a perfect combination that I am pretty sure will never go out of style! The best ankle boots to wear with skinny jeans are many. The type of ankle boot you choose to pair with your skinny jeans, can completely change the look of the outfit.

Of course, I could go into detail with all types of ankle boots to wear with your jeans, but that would take a few posts! So here are my top 3 ankle boots for skinny jeans to keep you stylish into 2022:


Shop 2021 Ankle Boots:


Stiletto Ankle Boots

stiletto ankle boots with skinny jeans

Shop Stiletto Ankle Boots:


Stiletto ankle boots are definitely a more slick version of an ankle boot that, depending on heel height and material, can work from the board room to the bar.

Styling tip: show a little ankle to add some je ne sais quoi to your stiletto shoe style!

Block Heel Ankle Boots

PAINTER Leather Star Stud Boots

Shop Chunky Heeled Ankle Boots:


Block and chunkier heel ankle boots are trendy & a lot easier to walk in than their stiletto counterparts. These are one of the most popular style of ankle boot to wear with skinny jeans at the moment. Wear them anywhere for an on-trend look! Extra points for wearing block heel sock boots 😉

Styling tip: The are the shoes to wear with flare jeans for the next few season too.

Low Heeled Ankle Boots

low ankle boots with skinny jeans

Shop Low Heeled Booties for Skinny Jeans:


Low heeled ankle boots equate low-key, but they can be seriously sleek. The easy go-to ankle boot that you can (hopefully!) walk for miles in.

Styling tip: the lower the boot on the ankle, the more awkward it looks to tuck your jeans into them. Try to keep a space between the jean hem & top of the boot, like the images above.

Combat Boots with Skinny Jeans

combat boots with skinny jeans

Shop Combat Boots for Skinny Jeans:


Show your tough side with a pair of lace-up combat boots paired with tight jeans. Add a destroyed skinny for maximum rebel effect! A solid leather pair of combat if well taken care of with last years. Combat boots get more or less trendy in fashion, but are always present.

This classic boot will surely never go out of style! Can’t beat the fact that you can pretty much wear them with anything. Not into lace-ups? A buckled biker boot will be just as tough & edgy, but easier to slip in & out of!

Styling tip: As this classic style sits a little higher at the ankle, feel free to show a little sock layered on top of the jeans

Over the Knee Boots with Skinny Jeans

over the knee boots skinny jeans

Shop Over-the-Knee Boots for Slim Jeans:


Skinny jeans with boots it brought to another level with over-the-knee-boot! They’re not only the hottest boots for the current and upcoming season, but they’re one of my personal favorite of all best shoes to wear with skinny jeans!

Whether low or high heeled, leather or suede, nothing beats skinny jeans with a thigh high boot for an updated, fashionable & sexy look. And now’s a great time to score a pair of these on major sale!

Styling tip: Over the knee boots with skinny jeans work best with jeans that fit snugly. These can look rather unsightly when caught bunching up above the top of the boot.

Trouble fitting your skinny jeans into your high boots? Well if they are too long, you can simply cuff them up once (so the it doesn’t add bulk inside the boot) & pull your socks over it before sliding on your boots.

Or you can wear a pant clip for boots to keep those jeans from bunching up & out of your boots!

Skinny Jeans and Peep-Toe Booties

ankle booties and skinny jeans

Shop Peep Toe Booties for Skinnies:


With a sexy sky-high stiletto, or trendy block heel, a cut-out, lace-up or cage bootie is a great choice of boot/sandal hybrid to wear with skinny jeans. Pair them to go on a date, a night out with the girls, this boot type will not disappoint & always ready show off a cute pedi!

Styling tip: I do love a shorter or cuffed skinny with booties to show off a little ankle, but that’s just personal preference.

The first image above left’s jean hem ends right at the shoe, while the middle pairing works well with a slightly slouchy skinny. But they both end roughly and tightly at the ankle as to not look too sloppy.

Riding Boots with Skinny Jeans

riding boots with skinny jeans

Shop Riding Boots for Skinny Jeans:


Fashion bloggers have often proven how great a riding boot can look tucked into a classic riding boot. Although riding boots are not on the top of the boot trend scale right now, like the combat boot, they’ve become one of the most classic & versatile knee high boots.

Just ask Kate Middleton! These are the perfect boots to wear with skinny jeans if your style is less trend of the moment & more demure.

Styling tip: Pair any tight jean, riding boot, striped long sleeve tee & plaid blanked scarf for an instant (& easy!) right-out-the-door outfit. Surely an American fashion blogger favorite!

Rain Boots and Skinny Jeans

Silver Hunter Rain Boots Outfit

Shop Hunter Boots for Skinny Jeans:


Yep, Hunter boots are oh-so popular & the fad is not dying down! I wore silver Hunter rain boots myself in a shoe styling post & they’re a fabulous high boot to beat a dreary, rainy day in style.

For all those reasons, that’s what it makes Hunters hard to omit from a what boots to wear with skinny jeans post!

Styling tip: These rubber boots are wide enough at the calf to fit even a looser fitting skinny, so no worries if your jeans aren’t tight enough.


Are sneakers more your thing? Heck, I love them too! Check out my post on the 5 most fashionable pairings of skinny jeans and sneakers!

xo ShoeTease