Fall Style Tip: How to Wear Booties with Jeans

by CWstyle

It’s ankle boot season! Every year about this time, I get questions from my clients about how to wear booties with jeans. This is a classic pairing, but things can get a little confusing with all of the trends in denim this year. We’ve seen a huge increase in the variety of jean lengths and types of hems like cropped, raw-edge, kick flares, straight leg and of course skinny jeans. The good news is, it’s actually kind of hard to get wrong!

ankle boots for fall

Here’s a quick guide for how to wear booties with jeans this fall!

Before we get started, I’d like to reinforce one point: Do NOT pull your jeans over your ankle boots. Unless they are bootcut or flared, your jeans should not cover the top of your ankle boot! Choose one of the following options for pairing your jeans with your ankle booties. 😊

Option 1: Cuffing

cuffed jeans with booties

A simple cuff is usually the answer to all bootie-related questions! The goal is to create a small separation between your hem and your boot – revealing just a sliver of skin. This elongates the leg and shows off the narrowest part of your leg. Go with a single or double cuff depending on what feels right – but keep the cuff to about ½ an inch to 1 inch. If your jeans are still too long with a double cuff, consider wearing a different pair that works better with the height of the ankle boot.

Option 2: Tucked

Tucked jeans with booties

OK, here’s a disclaimer. I generally do not advise the tuck for ankle booties, but sometimes it is the best option! BUT – only use this option with skinny jeans that are very close-fitting at the ankle. If you tuck, you do not want extra fabric bunching up in the top of your booties! For this option to work, your skinny jeans should hit at your ankle and the boots extend just a little further up.

Option 3: Cropped

cropped jeans with booties

There are so many fun trends in denim this year, and cropped hems is one of the most popular. With these styles, just let the jean fall where they fall. You still want a bit of skin showing – the ½ inch rule is in effect here too. For this pairing to work, the length of the crop will need to match up with the height of the bootie. I would still recommend a slim-cropped jean since you don’t want to add a lot of bulk or fabric around your ankle. For wider, more exaggerated crops, I would recommend a taller, slim-fitting boot – more like a sock bootie!

Option 4: Perfect Match

perfectly matched jeans with booties

Sometimes you put on a pair of jeans and boots and they work perfectly! No cuffing or tucking needed! Again, this perfect combo usually happens with ankle-length skinny jeans or ankle-length straight leg jeans and boots that are just a touch above the ankle. It should create a nice line down your leg with just a little break at the ankle to show some skin!

fall booties gif

Looking for some other style tips (here and here)? I want to know what other style questions do you have! Send me an email and I will answer it on my Instagram or in another blog post!

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