Frances Hall is a librarian and writing and women's and gender studies instructor. Just think of all the possibilities! When it gets cold, sometimes skip the ankle boots in favor of knee-high or over the knee boots, or I wear trouser socks with the taller ankle boots, when my jeans cover them.
When wearing straight leg jeans with ankle boots, try to achieve one long, lean leg line. Here is an example of how I styled a slim straight ankle length jean with suede block heel booties. But first, a caveat. Do not rely on retail websites to show the proper styling of boots and jeans.
However, I found a couple examples that I believe got it right. Here is an example I think shows too much space between the jean and the boots. In this next example, the hem of the jeans extends over the shaft of the ankle boot by about an inch, allowing for a smooth transition, even though there is high contrast between the mid-wash denim and the black booties.
This works without shortening the line of the leg too much, especially because the higher rise extends the jeans a couple inches at the top, compensating for the shorter leg length. This is why it works best to wear a cropped top or to just tuck in the top when wearing cropped jeans.
I find the shorter, boxy tops look best on me because I can leave them untucked. See the example above. I think this look also works well because the high-heeled, pointy-toe ankle boot is slimming and helps to visually lengthen the line of the leg. A flat boot might not work as well. The most important factor when wearing ankle boots with bootcut jeans is the length of the jeans. I also think bootcut jeans look best with a pointy-toe boot or shoe because it elongates the leg, but you can wear them with a rounded toe if you prefer.
I also prefer my bootcut jeans with heels, but again, flats are an option, but in that case a pointy toe definitely helps. Often the models wearing the jeans are too tall for the jeans they are modeling, but I rounded up an example that I think got it right.
Of course they are showing them with pumps, but they should look the same with booties. When pairing ankle boots with cropped bootcut jeans , the rules for the straight crop jeans apply. Ankle boots are a great way to update a classic skirt outfit. To keep a long, lean line, go for a monochromatic look. I tried this look with a denim skirt and really liked it. Also, the shaft is high and rather narrow, keeping my ankles looking slim, so they work well with skirts and dresses.
Sock booties are also trending right now, and they work best with dresses or cropped straight jeans. In theory, these chop up the line of the leg, but somehow the proportions seem to work because the dress is shorter, showing more leg.
So there you go! Subscribe to get email updates! This post contains affiliate links. When you shop through my links, it helps support my business at no additional cost to you so thank you!
Your email address will not be published. Save my name, email, and website in this browser for the next time I comment. Yours was most helpful. Thanks for all the good advice! I love hearing that!!!!
So glad to hear people are still finding me via Google and sticking around. I hope you and the girls thoroughly enjoy your final week of summer break. Have an awesome day! Enjoy your pool before the days get chilly! So informative with great examples, and up to the minute good advice!
Thank you for your work to keep the rest of us attire appropriate and fashionable!! Great post and helpful tips! Thanks for helping us navigate booties with different types of jeans. Enjoy your week and pool! The smoke is so oppressive out west from the hundreds of forest fires. Really looking forward to seeing blue skies again come fall. It feels apocalyptic here. This was so helpful as I purchased my first pair of ankle boots a few weeks ago.
I was wondering what type of socks you wear with these if they show a good amount of your foot. When it gets cold, sometimes skip the ankle boots in favor of knee-high or over the knee boots, or I wear trouser socks with the taller ankle boots, when my jeans cover them.
Jo Lynne, I have purchased 3 pairs of boyfriend jeans. They are rather baggy and loose but they are very comfortable. I wear the with a belt and tucked in T shirt.
Should I cuff the jeans and just show off my booties? Yes, I think boyfriend jeans generally look better cuffed. I almost included a look with boyfriend jeans and ankle boots. I can go back and add it. This is the best example I have: I always love seeing different ways to wear ankle boots like this, Jo-Lynne.
I think my favorite way lately is with dresses because it seems modern. My mom always complains about the cutting off the leg line. I had to get used to the look. I used to think it looked so clunky and stupid. I mean, I really hated it. I think it has to be done right, though. And with the taller boots, I feel like I can wear somewhat shorter skirts yet not feel sleazy!!
Shop for the Pieces: Everlane exact —wearing M Midi Skirt: Target really old, but similar HERE If you wear a high pair of boots, adding tights that match will extend your leg line and help prevent your legs from looking stumpy. The boot goes a couple of inches past my ankle and really cuts off my legs. To minimize that, I went with matching tights. My Tried and True Favorites! The pic above is taken from that post. This is my favorite tutorial on how to wear ankle boots with skinny jeans, and she shows 4 ways to do it.
On the left column are the single and double rolls with my jeans in their natural state. Instead, a skinnier leg makes things a little more streamline. This is my favorite pair 4 from the last post —the pair with the cutout in front. The toe is slightly pointed, and I think if they were pointier it would have looked even better with trouser jeans to elongate the leg. If your ankle boots look a little strange with trouser jeans, try a pair with a pointier toe.
I find that regardless of the cut of the dress pencil, a-line, or whatever else , the thing that makes or breaks it for me is the length of the dress. Above are a-line skirts at different lengths: My preference with FLAT ankle boots like these is slightly above the knee, though at the knee is okay too.
I mean, this boot can really do no wrong. Except that it has heels and sometimes you just really want flats no matter what… Shop for the Pieces: Target really old, but similar HERE. If you wear a high pair of boots, adding tights that match will extend your leg line and help prevent your legs from looking stumpy.
When it comes to ankle boots (basically any boot but knee-high or over-the-knee) and skinny jeans, I’m not a fan of tucking your jeans in the boots, or pulling them over the top of the boot. Leave those looks to tall boots and bootcut jeans. How to Wear Ankle Boots with Skinny Jeans Generally, boots with a taller shaft look best with skinny jeans tucked in, and boots with a lower shaft look better with jeans untucked or cuffed. Let’s break it . If you don’t want to wear skinny jeans, pair ankle boots with trouser jeans, but go for a pointier toe. For skirts and dresses, aim for hems that hit at your knee or slightly above. If the boot is high, pair it with same colored tights to extend the leg line.