While we all love a new pair of booties, there’s nothing worse than finding out your fresh pair of kicks is painful to wear. Fortunately, the shoes we offer on ShoeMall are comfortable and stylish, so it’s easy to find an adorable pair of boots that don’t cramp your style or your feet! Check out some of our favorites below!

Vionic with Orthaheel Serena

This classic ankle boot will never go out of style! In addition to the fact that this bootie is cute as can be, it has a weather-resistant protective coating and an easy side zip closure. Plus, it has a removable microfiber-wrapped EVA footbed and is recommended by Dr. Andrew Weil; needless to say, you’ll be crushing on comfort as soon as you put on this lovely bootie!

Bed:Stu Blaire

If you describe your style as funky with a bit of edge, then you’ll la-la-la-love this sassy ankle boot. Aside from the majorly cool distressed-look leather upper, our favorite aspect of this bootie is the fun lace-up detailing up the side; it’s the perfect way to “pumpkin spice” up your outfit this fall! Along with that, this boot has a lightly cushioned footbed and a sturdy heel, so you can expect to stay comfortable all-day long.

White Mountain Desire

It’s easy to make a fashion statement in a bootie this gorgeous! We love the stunning studs and strappy upper on this ultra-detailed ankle boot, but that’s not where our admiration ends. This must-have bootie has just a 1-1/2” heel, making it perfect for walking around town. Plus, it has a convenient side zip closure—what more could you ask for in a shoe?

UGG® Bandara Ankle Boot

Get ready to discover comfort! We love everything about this foot-friendly ankle boot from UGG®. Not only does this bootie look cozy with its suede leather upper, but also, it has a cushioning PORON® footbed, so you know this country-chic ankle boot offers endless comfort. Pair this trendy bootie with skinnies and a cold shoulder top for a great day-to-night outfit!

Madden Girl Eviita

Trust us when we say that you can transform any outfit in an instant with this fashionable ankle boot. This bold beauty features a lightly cushioned footbed and easy slip-on styling, and it even has goring for extra stretch! Oh, and P.S., perforations are trending this season—you’ll see ‘em on everyone and everything. With that said, this flattering ankle boot is a can’t-miss this fall!

Naturalizer Zarie

Meet the minimalist pair you’ll want to wear day in and day out! When you’re not sure what shoe to wear, you can’t wrong with this modern ankle boot. After all, it’s super versatile, and it has an N5 Contour cushioning footbed and a wee 1-7/8″ stacked-look heel. Yes, please!

Madden Girl Naash

Get ready to step into your comfort zone! From the subtle cutouts to the sassy studs, this ankle boot by Madden Girl is every country cutie’s dream. That’s not all this ankle boot has to offer, though; it offers easy pull-on styling and a cushioned footbed, so comfort and a relaxed fit is a guarantee. Plus, you don’t need to worry about tripping in these babies because it has a low 1-1/2″ heel; i.e., the perfect amount of height!

What’s your favorite pair of comfy yet chic booties? Share your thoughts with us in the comments section, and show us your amazing boots via Facebook, Twitter and Pinterest today!