How to Wear Ankle Boots with Jeans

Once you’re in the doldrums of winter it can be hard to feel inspired by your closet.  You feel like you’re on repeat–the same boots and jeans or dress and coat every day.  But these closet staples don’t have to be boring; you can feel inspired again and I can show you how to wear ankle boots with jeans in a new and fresh way.  Sometimes you just need to see a little inspiration to help breathe life into your old closet. Figuring out how to wear something in a new way at the end of the season can be a challenge–but I’m here to help!

How to Wear Ankle Boots with Jeans

All cuts of jeans work

Skinny jeans, wide-leg jeans, boyfriend jeans–they all work with booties.  In fact, bootcut jeans are making a huge comeback with ankle boots, too.  I mean, aren’t boot-cut jeans destined to be worn with boots?!  Show off thee top of your booties!  Lately, booties with straight leg jeans are my favorite.

Show some skin

I love a little sliver of ankle showing (weather permitting) so a pair of cropped jeans can fit thee bill.  It breaks the leg line nicely; if your jeans are too long and you’re not interested in cutting the hem raw, consider cuffing your jeans.

Make your legs look a mile long

You know what will make you look super long and lean?  This illusion: wear long, black, legging jeans (full length jean, no skin showing) + black heeled booties.  You could even try a sock bootie!

Jeans + Booties Outfit Ideas

High Contrast: White Jeans with Cognac Booties

Like I mentioned before, I love a good contrast.  It pleases the eye and makes your outfit feel very intentional.  A deep, rich chestnut, cognac ankle bootie with white jeans is a show stopper for sure.  Add a sweater that gives off pre-spring vibes, like this Eleven Six knit–it’s perfect for spring!

how to wear ankle boots with jeans
Eleven Six sweater (shop more Eleven Six here), Everlane jeans, Sarah Flint booties (use code ANNAJANE50), Celine bag
Classic Chic: Black Booties with Everyday Denim 

Distressed denim loves being paired with ankle boots.  It’s the same Sarah Flint chestnut bootie that’s seen above (very comfortable, by the way) with a slightly cropped AND cuffed black jean.

How to Wear Ankle Boots with Jeans
ASTR sweater (shop more ASTR here), Polene bag, Paige jeans, Sarah Flint booties, Ray Ban sunglasses (shop more Ray Bans here)
Preppy Rocker: Edgy Black Booties with Classic Denim

I love this juxtaposition–some slightly edgy black booties with a pointed toe paired with preppy denim and classic layers.  It sets it off and makes it a little different, but in a good way!  (That’s a sold out one/third blazer, by the way–more to come this spring!)

How to Wear Ankle Boots with Jeans
Madewell coat, One/Third blazer (sold out but more coming this spring!), Citizens of Humanity jeans, Tamara Mellon booties, Polene bag
Opposites Attract:  Coastal white meets cowboy ankle booties

You KNOW I can’t resist a white on white look.  But with cowboy ankle boots?  Sure!  It’s unexpected but the palette is tonal so it goes.  Once March hits, we need all the tricks in the book to keep things interesting, people.

spring white with booties
Everlane jacket, Everlane jeans, Goyard bag, Everlane booties, RayBan sunglasses
On the Edge: Trendy Snakeskin With an All Black Look

All black is always a good idea.  It’s even better when paired with an unexpected texture like these snakeskin booties.  I can’t tell you how much I loved wearing these boots this fall–and I am going to keep wearing them into spring!

how to wear ankle boots with jeans
Everlane coat, Everlane booties, Everlane sweater, Everlane jeans, similar J Crew Factory sunglasses, Goyard bag
Casual Cool: Boyfriend Jeans with Snakeskin Ankle Boots

I told you that a boyfriend cut of denim looks just as good with ankle boots!  Don’t be scared of the baggier proportions–it can look chic when slightly cropped and when the boot in question is sleek.

How to Wear Ankle Boots with Jeans
Everlane coat, Everlane alpaca sweater, Everlane boyfriend jeans, Everlane booties, Goyard bag
Matchy Matchy: When the Handbag Matches the Booties

I love a good game of matching–especially when it involves my handbags and footwear.  These old Marc Fisher booties perfectly match my old Celine belt bag and it’s a match made in heaven.

how to wear ankle boots with jeans
Cuyana coat, Marc Fisher booties, Madewell scarf, Celine bag




  1. Ok — am I the only one who needs help with socks when it comes to ankle booties!? Some booties rub and hurt if I don’t have socks up past their edge… How do I make the socks look right?

  2. Can I just say this is Shop Your Closet all grown up? Love how you distilled into words the details that differentiate the same ole outfit combo. Also a great segue into the resurgence of past classic looks. Really great job!

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