Three Ways to Wear Ankle Boots with Skinny Jeans | One To Nothin'

Three Ways to Wear Ankle Boots with Skinny Jeans

I distinctly remember chatting with my BFF in high school about how we couldn't "pull off skinny jeans." Back then it was all about the bootcut and we were convinced our legs looked like sausages cooped up in those skinny thangs. These days it feels like quite the opposite situation, and I have to gather up my courage to rock flares. The only problem, after accepting that my legs actually just look like normal legs in skinny jeans, was that I didn't know how to wear them with the giant collection of ankle boots I had acquired. I would try to tuck them into the boots and feel weird when my short legs caused my too-long-always-unaltered-and-slightly-bunchy bottoms of my pants to bulge out.
I'm not sure when exactly the revelation hit me, but one day I decided to try rolling the cuffs. I was skeptical at first because I didn't want to look like I was wearing capris in the fall, but I think I finally got it down and I figured I'd share my discoveries with you guys. Although chances are, you savvy ladies of Blogland figured this shiz out long before I did.

Three ways to wear skinny jeans with ankle boots:
1. The Mini Roll - This is my personal favorite. It's a micro fold starting at the seam, one more of equal size and boom, done. This one is imperfect. I like when it looks a little undone, like "Oh, these? They were just like that when I pulled them on this morning." This fold does require a more true-to-length pant though. Before I realized this was my favorite way to wear jeans, the majority of mine were at least a few inches too long and those bunchy bottoms I once loved are not conducive to The Mini Roll.

2. The Fake Hem - Those bunchy bad boys are, however, perfect candidates for The Fake Hem. This technique requires a fold under to make it look like you've got it together enough to ever actually go to a tailor to get your jeans altered (HA!). It's great for a more polished look, and depending on the boot, it could elongate the legs in a Jessica Rabbit kind of way.

3. The Big Cuff - This technique is basically the same as The Fake Hem but inside out. Just fold a few inches up and call it a day. This is great for summer looks too, but I'm wearing this one here. The Big Cuff is quick, easy and much easier to make uniform on both sides than The Mini Roll.

Then there's always the tuck in technique. If it's cold enough out, all bets are off -- you tuck those babies in and forget all about the bunching dilemma. 

The Perfect Booties for Fall

Now that you've got your skinny jean situation covered, it's time to build that ankle bootie collection. Above are some of my current faves from Shein.

What's your favorite way to wear ankle boots and jeans?

Original photos by Becca Wyant for One to Nothin'. All rights reserved.


  1. Just in time for my new treat yo'self ankle booties that are waiting for me in the apartment office. I'll have to try the fake hem, I've never seen it and maybe I'll set a trend.

  2. I have a pair of ankle booties and I never know what the heck to do with my pants. I feel like every option I try looks awful haha. maybe I should try again.

  3. Good idea about the fake hem! I definitely have some jeans that would fit into that category.

  4. Great guide! I definitely stick with the fake hem with booties if I don't take them in for a real hem. My short legs just can't rock the boot and rolled hem combo. :(

  5. Super helpul, but I find I struggle with boots because I simply cant wear them with anything BUT skinny fit jeans haha x

  6. Oooooh, I've never thought of rolling my jeans underneath! Which is odd considering that ankle boots and jeans is my signature outfit but now I have something for next season, haha!

    Kyah /

  7. This depended on an investigation of 1,601 West Point cadets who took an interest in ball with no history of ankle sprain or flimsiness. Subtalar Joint


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