Rolled Hem Image source: I know — not cheap!
This post outlines the socks for ankle booties I personally found best, and still wear on constant rotation. These are my favorites and I really should buy some more.
Coming in a variety of graphic prints and color combinations, they are fun to wear and made from the thickest fabric out of any other socks I tried. They feel warm on the feet and are just thick enough to snugly fill my ankle boots so they fit secure without any slipping and sliding.
The toe box and heel both fit securely, and there is a silicone strip at the heel to prevent slippage. These rarely, if ever, slip off my heel, which makes them a comfortable sock. These are slightly less reached for than my Stance socks, but a good option nonetheless. Also coming in lots of colors and prints, these are fun little socks that get the job done. A little thinner fabric than Stance, and also have a silicone strip at the heel to prevent slippage. These tend to sit a little lower on my heel, so these slip every now and then, but not often enough to make me not want to ever wear them.
These fit nicely, if not a little bit snug, so these are a great option for anyone with smaller feet than my own. Once again, these have a silicone strip at the heel to prevent slippage, and rarely cause me any problems. These are a great cold weather option as they come in a toasty wool blend, and feel the thinest of the bunch. I also find these to run a little longer than the other brands, so they may not work as well for anyone with a smaller shoe size than my own.
I also want to try this lower cut style. Weird, I had the exact opposite experience with Stance Invisible vs. And I have slightly larger feet than you! Straight leg jeans are trending this fall , particularly the cropped styles. The good news is, these styles look great with ankle boots! 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.
This post on how to wear ankle boots is one of my most popular, but I do believe it is time for an update! There are soooo many styles of ankle boots and so many styles of jeans that it is a bit of a sticky wicket, figuring out how to style your ankle boots, so I’m here to help! I’m sharing 5. All of my booties are tight around the ankle and I really think these socks will look best with a wide ankle style of bootie, like this gorgeous pair of Sam Edelman boots. Yes, I think those socks and these booties will make a pretty stunning combo. Tis the season for warm, woolly socks! I agree that the low boots with a front dip don’t look so great with thick socks. I have some low, flat skater-style boots that I can wear with chunky socks and boyfriend jeans but the proportions are different.