How to Wear Booties with Jeans: Style Tips & Outfit Ideas

Ankle boots are a great wardrobe staple, but knowing how to wear ankle boots with jeans is confusing. In this post, read through some tips on styling booties with different cuts of jeans and get inspiration for your next outfit.

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With jean styles evolving, a lot of women have questions on how to wear ankle boots with their jeans. Whether it be skinny jeans, straight jeans, or dad jeans, we are going to cover options for various jean styles.

No matter what your jean preference, you will (hopefully) find some helpful tips in this post!

Why Styling Jeans with Ankle Boots is So Confusing

When deciding on what to wear, I am convinced the source of most frustration comes from the quantity of options. There are simply too many options and combinations to consider. This is one reason I began exploring capsule wardrobes nearly two years ago.

Styling jeans with ankle boots is no exception to this theory. Many women feel overwhelmed because of the many variations of ankle boots AND there are also several fits of jeans to consider.

Knowing how to create the perfect combination is overwhelming.

First, let’s look at the different booties we have to choose from:

• Short shaft boots: these usually hit at the ankle or below
• Mid-length boots: this shaft hits just above the ankle
• Tall ankle boots: sit an inch or two above the ankle

Second, three jean types that are on trend today (each available in various lengths):

• Skinny jeans
• Slim Straight Jeans
• Relaxed/Wide Leg Jeans

 

 

Dos and Don’ts: Booties with Jeans

From personal experience, the boot shaft is the key characteristic to consider when pairing booties with jeans.

Do Pay Attention to Boot Shaft Height

The goal with many outfits is to create the appearance of a long, uniform leg line. Therefore, the wrong shoe and jean combination can easily create bunching at the ankles and result in a choppy look. Here are a few tips for wearing boots with particular jean fits.

SLIM STRAIGHT JEANS

DO: Wear a taller & narrow shaft ankle boot 

DON’T: Wear short ankle boots as this may cause jeans to bunch at the ankle.

 

SKINNY JEANS

DO: Wear short ankle boots with cuffed skinny jeans or ankle skinnies. I prefer to have about an inch of ankle showing with skinny jeans and short ankle boots. Boots with a taller shaft should be tucked in, without any leg showing.

DON’T: Wear skinny jeans OVER the shaft of an ankle boot. This creates bulk, rather than a clean straight line

 

RELAXED/WIDE LEG JEANS

DO: Wear boots with a taller and narrow shaft. The goal is to have the jeans rest over the shaft without any bulk, and to conceal all skin on the leg.

DON’T: Wear boots with a short shaft. 

 

 

 

What Jeans Go Best With Ankle Boots?

As you can see, most jeans styles can be worn with ankle boots however, the boot style must be considered alongside the jean style. Otherwise the pairing could be completely wrong. 

It is also important to consider your personal style and body shape when deciding how to wear booties with different cuts of jeans. Comfort is always important so that you look and feel confident. What works for me, may not look right on you. So have fun with it, and if one combination doesn’t work, try another! 

Let’s dive deeper into each jean fit.

How to Style Booties with Skinnies

Skinny jeans aren’t as popular as they were in the past, but they are a beloved staple by many women. I don’t think they’ll ever be out of style, but it is important to be mindful of styling them to avoid looking outdated.

When wearing skinny jeans with ankle booties I prefer both the leg opening and the ankle boot shaft to be rather tight on the ankle and leg. This create a nice elongated leg line. 

To wear this combination, I like to show just a slight gap between the boot and jeans.

To do this with a long inseam and short or mid-length ankle boots, simply cuff the jeans up slightly. Avoid a super bulky cuffs though! 

 

Mid-length ankle boots work great with ankle skinnies and may not require a cuff as they will naturally create a gap between the pants and boots.

 

Boots with taller shafts could be tucked into the shaft of the boot if the jeans are long enough to STAY tucked throughout the day.

 

How to Wear Ankle Booties with Slim Straight Jeans

Slim straight jeans are in between skinny jeans and wide leg jeans. This relaxed jean style is very popular this year and is also a great style to pair with ankle boots.

Slim straight ankle length jeans are best to be worn with short shaft booties. This will create a nice spacing between the jean and the shoes and be very flattering.

 

Mid-length and taller shaft boots in regular or long length should be worn over the boot shaft. This look works best with a narrow/fitted boot shaft. A wide boot shaft will create a bulky look at the bottom of the pant leg.

Avoid tucking this jean style into your ankle boots. In my opinion, this looks heavy, bulky, and is not flattering in most cases.

 

 

How to Wear Ankle Booties with Relaxed Fit Denim

High waist relaxed jeans are in style right now and I love it! They are comfortable and extremely versatile when it comes to styling with footwear. 

When it comes to ankle boots, wearing them with relaxed denim is EASY! No tucking, cuffing, bunching required. Most wide leg style jeans will sit nicely over any shaft height of ankle boots.

The untucked look, creates a nice, long, flattering leg line. These same guidelines apply for flare and bootcut jeans as well.

 

ANKLE BOOTS OUTFIT IDEAS

BODY SUIT + RELAXED JEANS + MID SHAFT ANKLE BOOTS

 

BUTTON DOWN + RELAXED JEANS + MID SHAFT BOOTS

 

COATIGAN + SCARF + SKINNY JEANS + MID SHAFT BOOTS

 

TIED BUTTON DOWN + SLIM STRAIGHT JEANS +TALL ANKLE BOOTS

 

TUNIC + CUFFED SKINNIES + SHORT ANKLE BOOTS

 

CARDIGAN + ANKLE SKINNIES + MID SHAFT BOOTIES

 

 

LONG CARDIGAN + ANKLE SKINNY JEANS + MID SHAFT BOOTIES

 

 

THIS POST WAS ALL ABOUT HOW TO WEAR JEANS WITH ANKLE BOOTS.

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