ACCESSORIES

5 Ways To Wear Skinny Jeans with Ankle Boots…Keeping It Simple!

Ankle Boots With Skinny Jeans

Right now, everyone is saying that skinny jeans are out of style. And I’ve definitely hopped on the baggy jeans bandwagon. But I still love my skinny jeans and won’t get rid of them. And it’s still important to know how to style them! With fall around the corner, we’re all thinking about swapping our shorts and sandals for jeans and boots. Which always brings up the question…”How do I wear my ankle boots with skinny jeans?” I get this question A LOT. Wearing ankle boots can be difficult for many reasons, which I’ll share more about below. But I have a few ways to make it a little easier on you!

If you’re interested in how to style other denim styles with booties, make sure you check out this post.

Ankle Boots, How to wear skinny jeans with ankle boots, try cropped jeans, by fashion blogger over 40, Erin busbee, Telluride, Colorado

How to wear skinny jeans with ankle boots, try cropped jeans, by fashion blogger over 40, Erin busbee, Telluride, Colorado

Ankle Boots, How to wear skinny jeans with ankle boots, try cropped jeans, by fashion blogger over 40, Erin busbee, Telluride, Colorado

Ankle Boots, How to wear skinny jeans with ankle boots, try cropped jeans, by fashion blogger over 40, Erin busbee, Telluride, Colorado

Ankle Boots, How to wear skinny jeans with ankle boots, try cropped jeans, by fashion blogger over 40, Erin busbee, Telluride, Colorado

Why It’s So Hard To Wear Ankle Boots With Skinny Jeans

This is a common issue and here’s why…

1) Every pair of jeans is a different length.
If you buy a cropped pair, it is likely between 25″ – 29″
“Regular” jeans vary between 30″ – 33″
A 33″+ inseam is ideal for taller women

2) Booties are all varying heights
Some fall below the ankle bone, while others are almost mid-calf.

3) And, WE are all different sizes.
After dressing 100’s of women, I can tell you with certainly… no two women are shaped alike!
This further complicates things. If you missed this post on how to determine your body shape, make sure you check that out!

But, don’t worry, I’m sharing FIVE very simple and stylish ways to wear your ankle boots with your skinny jeans below.

Ankle Boots, How to wear skinny jeans with ankle boots, try cropped jeans, by fashion blogger over 40, Erin busbee, Telluride, Colorado

Option #1) Cropped Jeans

This is the easiest way to style your ankle boots…just wear cropped jeans! Cropped or ankle jeans, mean they have a shorter inseam, usually 25-29 inches. The pair of jeans I’m wearing above have a 27” inseam, which works perfectly with my ankle boots. If you have a pair of jeans you love to wear with your skinny jeans, look at the inseam on those and try to buy 1-2 more pairs of jeans with the same inseam. It will definitely make your life easier!

If you don’t already have the perfect pair of cropped jeans to go with your ankle boots, you want to look for a pair where the cropped hemline falls just above the top of your ankle boots so that there’s a tiny sliver of skin between your boots and your jean hemline.

Shop cropped & ankle-length jeans here.
Shop ankle booties here.

Ankle Boots, How to wear skinny jeans with ankle boots, try cropped jeans, by fashion blogger over 40, Erin busbee, Telluride, Colorado

Option #2) Big Cuff

If you are petite like I am, you might want to go with…the big cuff! It will raise the hemline of your jeans by 4 inches or more. I have to do this with almost ALL of my skinny jeans that aren’t a cropped/ankle length. Not all jeans look good cuffed like this, so be sure to try them out first!

Ankle Boots, How to wear skinny jeans with ankle boots, try cropped jeans, by fashion blogger over 40, Erin busbee, Telluride, Colorado

Option #3) Double Cuff

Your third option is the double cuff! My petite ladies may also enjoy this one. You cuff your jeans about an inch and then you cuff them again…yes, that’s that easy! This should raise your jeans by about 4 inches as well. By the way, these Rag & Bone jeans are some of my favorites to wear cuffed or uncuffed with ankle boots!

Ankle Boots, How to wear skinny jeans with ankle boots, try cropped jeans, by fashion blogger over 40, Erin busbee, Telluride, Colorado

Option #4) Tuck Jeans Under

A quick way to make your long jeans a little shorter so they don’t compete with your ankle boots… tuck them under. To keep your line looking long and lean, wear dark-colored jeans and ankle boots. The tuck under makes your jeans look classic and again keeps you looking taller.

Ankle Boots, How to wear skinny jeans with ankle boots, try cropped jeans, by fashion blogger over 40, Erin busbee, Telluride, Colorado

Option #5) Tuck Jeans Into Booties

I love simple solutions… when you have booties that are on the taller side, like the pair I’m wearing above, all you have to do is tuck your jeans into the boots!

Ankle Boots, How to wear skinny jeans with ankle boots, try cropped jeans, by fashion blogger over 40, Erin busbee, Telluride, Colorado

Other Styling Suggestions
  • Wear taller boots over skinny jeans.
  • With booties that are fitted to the calf, wear the boots under your jeans. This style of booties is perfect to wear under straight, tapered, and wide-leg jeans.
  • If your booties aren’t fitted to the calf and they are taller, more like mid-calf booties, try cuffing your cropped jeans. (works best on skinny and straight-leg jeans)
  • Over-the-knee and knee-high boots always go over skinny jeans.
  • To keep you and your legs looking long and tall, go with the ‘tuck under‘ or ‘tuck in‘ methods. And be sure to wear booties and jeans that are both dark colors.
  • Make sure to wear no-show socks so the tops of the socks don’t peep out.

Ankle Boots, How to wear skinny jeans with ankle boots, try cropped jeans, by fashion blogger over 40, Erin busbee, Telluride, Colorado

Favorite Denim Brands & Boots Brands

My favorite denim brands are Moussy Vintage, Rag & Bone, Citizens of Humanity, AG, and Mother. For affordable options, make sure to check out Express!

My favorite boot & booties brands vary. But for basics, check out Paige, Louise et Cie, Steve Madden, Marc Fisher, Vince Camuto, and Rag & Bone. For weatherproof options, I love Sorel, Blondo, and La Canadienne.

Do you still have questions about styling your skinny jeans and boots? Please leave a comment below! And make sure you check out this post with even more tips on styling your boots with straight jeans, flare jeans, and more!

To get my blog posts delivered directly to your inbox, along with some awesome freebies, be sure to sign up for my newsletter here.

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How To Manifest Anything, Fashion blogger Erin Busbee of Busbee Style wearing an orange and blue Staud Ina dress with white sunglasses walking around in Telluride, Colorado
Erin Busbee
After a decade in TV news, a desire to help women "look pretty" sparked a career pivot. I started my own wardrobe consulting business, styling "real" women for many years. In 2014, I changed direction again, using my TV background and styling expertise to launch this website and my YouTube channel. We are now a community of nearly 700,000 dynamic, vibrant, amazing women over 40... who know that age isn't something you need to hide from. For us, life is just getting started!!
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11 thoughts on “5 Ways To Wear Skinny Jeans with Ankle Boots…Keeping It Simple!

  1. This was the first video of yours that I watched and I love your style! Can you recommend another bootie that is close to the Rag and Bone suede bootie in stone sand because Nordstrom sold out!

  2. I have watched your channel for a long time, very informative, could you please do a blog on best watches to wear for business, casual and
    Dressy, as a business person I do not leave my house without wearing my watch as I do not always have my phone nearby and I think
    It. Looks very professional for women and men. Linda, Toronto, Canada

    1. I think you have a LOT of wonderful watch options… depending on your preference. you can wear an over-sized watch or a smaller, more dainty watch. I really love the big, chunky ones that have mixed metal bands so they go with everything. You can also pair them with a couple of great bracelets…for extra pop!

  3. Your fashion sense is on point! I enjoy your videos and blog soo much. I much prefers blog posts about functional type of outfits, whether it be for the office, running errands or special events. Editorial fashion is fun and inspirational but not exactly functional. Keep up the awesome job of giving women (“grown up women”) great styling tips. The outdoor photos are beautiful.

    1. Thank you so much, Celina! I hear you… functional is the MOST helpful! I DO like to sprinkle in a little fun fashion every once in a while, but my primary focus and passion is definitely fashion AND function. Thank you for your sweet, supportive words! I’m really grateful… Erin xo

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