How to wear ankle boots with jeans – and the best ankle boots to choose this season

It’s a combination that you can wear pretty much any time of year. But a pair of ankle boots with jeans is particularly good for transitional times such as summer into fall or winter into spring when it’s not cold enough for big boots but too cold for sandals. But how to wear ankle boots with jeans for the most flattering efffect? Let’s take a look.

What kind of jeans go with ankle boots

You can wear any type of jeans, whether skinny or wide with ankle boots. But the way you wear them to get the most stylish look will differ.

What the problem can be with wearing ankle boots with jeans

Just as within any outfit, wearing your jeans and ankle boots is a question of balance. You need to think about where your ankle boots end as the attention will be drawn there. It’s also important to think about how your jeans will sit. You will want to tuck them in or make sure they sit above your ankle boots so they don’t bunch up.

Now, let’s take a look at some of the different jeans styles you could wear with your ankle boots.

Cropped jeans

Cropped jeans can look very stylish with your ankle boots. The key is to leave a little bit of ankle showing.

Sandra @lapecosapreciosa above shows a fabulous way to wear your ankle boots with jeans. She sticks to a neutral palette for her clothing and adds pops of color with her accessories.

Check out this similar blouse, jeans, cardigan, booties, handbag and earrings.

Urban CoCo Office Blazer – Nic +Zoe top – Levi’s straight leg jeans – Vince Camuto leather tote – PiePieBuy tie knot bootie – Akola pendant necklace

Tuck your jeans in

If you have skinny jeans, you can tuck them into your boots. Leaving them out can mean they bunch around your ankles and they don’t properly fit over your boots, so it’s best to neatly tuck them in.

Karen @styledbykaren above matches her boots to her jeans for a leg-lengthening look.

Get her look with this similar top, jeans, belt, booties and cardigan.

Caslon funnel neck sweater – Free People shirt jacket – Wit & Wisdom skinny jeans – STQ combat boots  – Malibu Skye knotted tote

Cuff your jeans

You might want to crop your jeans because they’re not quite the right length. Perhaps they’re slightly too short to tuck into your boots but slightly too long to be cropped.

Heidi @mams_middleagedmomstuff above shows how you could cuff your jeans so they sit just above your boots.

Check out these brown boots from Nine West and Bed Stu that you can wear with this similar top, jeans, belt and earrings.

Romwe knit sweater vest – Tommy Bahama boyfriend shirt – AG slim jeans – Soda lug sole boot – COACH leather shoulder bag – Madewell hoop earrings

Wear your jeans over your boots

If you have bootleg or wider jeans, it’s best to wear them over your booties. Make sure that your jeans end further down your boots rather than at the top of your booties.

Dawn Lucy @fashionshouldbefun above (read her style interview here) chooses on-trend green booties.

Get her look with this similar long sleeve top, jeans, booties and tote.

JLUXLABEL belted jacket – Ted Baker London print camisole – Joe’s bootcut jeans – Frye harness back zip bootie – Lola Mae quilted crossbody bag – Kendra Scott drop earrings

The best boots to choose

Now that you’re thinking about the jeans and ankle boots combinations you could put together, take a look at some of the most stylish ankle boots you could choose now…

lucky brand booties

If you’re looking for an absolute classic pair of boots you can wear season after season, a pair of black ankle boots will be perfect. If you already have a pair of black boots and want a different shade, you’ll find the Lucky Brand booties (below) come in a big choice of colors and prints.

Lucky Brand Basel Ankle Bootie

frye boot

With a nod to cowboy boot styling, the Frye ankle boots (below) would look good worn with your jeans, but also with your summer dresses to give them longevity.

Frye Ray Harness Back Zip Ankle Boot

hush puppies

It may be that you are looking for a comfort boot option that you can wear day-to-day. The Hush Puppies ankle boots (below) have a molded footbed.

Hush Puppies Mazin Cayto Ankle Boot

lifestride boots

If you want to add a little height, the LifeStride booties (below) will go with any style of jeans. The crisscross buckle details add interest. Reviewers say they are comfortable to wear all day.

LifeStride Jezebel Ankle Boot

cole haan

The Cole Haan booties (below) are sure to add impact to any outfit, particularly if you choose a striking color such as the navy blue shown here. Some reviewers say they run a little small, so you might want to think about sizing up.

Cole Haan Jensynn Bootie Ankle Boot

anthropologie

For an option you could wear for day or night, the Anthropologie boots (below) feature a low heel and would look good worn with skinny jeans tucked into them or under your bootleg jeans.

Anthropologie Silent D Tintel Heeled Ankle Boots

combat boots

Casual, combat style boots are particularly on trend right now. The STQ combat boots (below) have more than 8,000+ largely positive reviews.

STQ Combat Boots Lace up Ankle Booties

peep toe booties

If the weather isn’t yet very cold, you could think about wearing a pair of bootie-sandal hybrid shoes to add a little edge to your outfits.

J. Adams Maddie Peep Toe Booties

kitten heels

If you want a pair of booties to wear for smarter evening occasions with your jeans, a pair of kitten heels could be the ideal choice.

Clarks Linvale Sea Boot

western style boots

For a more casual look, a pair of cowboy style boots may be a good day-to-day choice. I would tuck your skinny jeans into the Rocket Dog boots (below). Reviewers say they are cute and comfortable.

Rocket Dog Sayla Western Boot

wedge boots

If you want to add some height but you don’t want to wear a hard-to-walk-in heel, you could choose a wedge heel instead. The Dr. Scholl boots (below) come in either black or brown.

Dr. Scholl’s Shoes Double Boot

buckle booties

For another casual option to wear everyday with your jeans, the LifeStride booties (below) feature a stylish plaited buckle detail.

LifeStride Adriana Ankle Bootie

cutout booties

The cutout detailing on the Vepose boots (below) add interest. I would wear with your cropped or cuffed jeans so you can see the pattern.

VEPOSE Cutout Ankle Boots 

lug soles

Lug soles are particularly on-trend this year. Plus, they are practical as they will help to prevent you slipping in wet or icy weather.

GLOBALWIN 17YY12 Boots

bow style booties

The bow tie feature on the PiePieBuy booties (below) will add a little romance to your look. Reviewers say they are trendy and comfortable.

PiePieBuy Tie Knot Ankle Boots

white boot

White boots have been on trend for a few seasons now and are definitely still in style for the upcoming season. Claudia @beafitmom.nl above tucks her skinny jeans into her calf-length white boots.

Steal her look with this similar sweater, jeans, boots and crossbody bag.

Soda Pilot Chelsea Boot

taupe boot

Another big trend this year is to choose a pale beige or taupe pair of booties like the Jeffrey Campbell boots (below).

Jeffrey Campbell Square-Toe Ankle Boots

How do you like to style your ankle boots with your jeans?

Continue reading:

1. The Best Winter Boots For Women: Stylish Winter Boots That You Can’t Wait To Wear
2. How To Wear Jeans Over 40 – Guidelines And Lots Of Ideas
3. The Best Wide Calf Boots For Winter And Fall

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Feature image by Dawn Lucy @fashionshouldbefun

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