Styling Advice

How to Wear Booties with Skinny Jeans

posted on February 19, 2014 | by Amanda Holstein

How to Wear Booties with Skinny Jeans

I get this question all the time. How are you supposed to wear booties with skinny jeans? Seems simple, but there really are a lot of options. And the answer changes depending on the ankle boots, the length of the jeans, the style of the jeans – it can get complicated. So I thought I’d break it down as simply as possible in today’s post. As an avid bootie wearer (in fact, I’m slightly obsessed), I can say that this has worked well for me. So here we go, how to wear booties with skinny jeans:

What length should my jeans be?

First, your jeans need to be the right length. I recommend ones that hit midway down the ankle. This way they aren’t too long that there’s extra fabric, or too short that you can’t have some fun rolling them.


What socks should I wear?

The perfect sock to pair with your booties has to be the ankle sock. Opt for a simple pair, not ones you workout in, just something simple. I usually choose darker colors in case you can see the sock a tad inside your boot. My go-to socks for booties are the Classic Ankle Socks from Gap.


How do I wear booties with skinny jeans?

Option 1:
If your jeans are the right length, you should be able to wear them with your ankle boots without rolling them. Just pull the jeans all the way down so any extra fabric is scrunched at the bottom. Let the jeans fall casually onto the boot – some of it might fall inside the boot, some may be left outside. Just a sliver of skin should show. If your jeans are the right length, they will look fine.


Option 2:
If there is too much fabric at the bottom when you pull your jeans down, you can also scrunch them up. Since these are skinny jeans, you can pull them up so more fabric sits around your knees and lower thighs. Pull your jeans up so that no more than 1.5 inches of skin is showing just above the boot.


Option 3:
My favorite way to wear booties with skinny jeans is to roll the bottom of the jeans twice. Keep the rolls nice and small for a seamless look. You should leave about 1 inch of skin showing just above the boot.


Option 4:
Another fun option is to just cuff the jeans once. If your jeans are too long, this won’t work – the cuff should be no more than 2 inches. Leave just an inch showing above the boot.


Now here’s what how you shouldn’t wear booties with skinny jeans. Avoid pulling the jeans over the boots so that no skin shows. This may just be a personal preference, but I’m just not a fan of this look.


Booties available in black here. Similar ones here.