Cute outfits to wear with ankle boots

As we load up on all our fall fashion favorites — plaid, anyone? — before the snow flies and winter becomes a reality, be sure to get enough time with trendy ankle boots.

“If there’s one piece you need, it’s the versatile ankle boot,” according to Bazaar. “Whether worn with a dress, skirt or jeans, ankle boots go with virtually everything in your closet, making them the ultimate footwear MVP.”

In the spirit of backing our MVP, we have put together cute outfits to wear with ankle boots and can show you how to wear ankle boots to work, other ideas on what to wear with ankle boots and how to style them. All of these outfits feature thrift store clothing finds.

There’s no time to waste!

How to wear skinny jeans with ankle boots

When it comes to cute outfits to wear with ankle boots, it doesn’t get any better than skinny jeans. Leggings are a close second in our book! Show off your ultra sense of style with a pair of dark skinny jeans, a soft puffy vest and a classic chambray shirt. Top it off with a cozy scarf and a pair of camel ankle boots and you’re ready for a beautiful fall day!

How to wear ankle pants and boots

Fitted, colored ankle pants are a great way to show off a pair of ankle boots, plus they’re also a way how to wear ankle boots to work. They can be the perfect combination of comfort and casual while looking put together. For what to wear with ankle boots, we are all over this pullover ivory sweater paired with these deep brick red pants that will have you stylin’ with on-trend wedge camel ankle boots.

How to wear ankle boots to work

For an office setting, go with a monochromatic look that appears both effortless and professional. Put that wardrobe must-have black pencil skirt to work for you and pair it with a blouse or top. We can’t say enough about a simple top like this one from Banana Republic that features enough detailing that the only accessory you need is a pair of dangly, eye-catching earrings. Black tights and ankle boots with heels complete the look. You’ll bring your A game with this one!

How to wear ankle boots

Once you’re all set with what to wear with ankle boots, you might need a primer on what to do with your pants so they are properly styled at the ankle. This primer on how to wear ankle boots will show you how to style ankle boots with pants, jeans, skirts and dresses. Just remember you don’t want them to look too bunchy. Cuffing or tucking is where it’s at!

About Goodwill: Goodwill NCW is a not-for-profit human services organization that in 2017 helped improve the lives of more than 70,000 people across 35 counties in north central Wisconsin. Goodwill NCW is one of four companies in the nation to be honored with a Platinum Well Workplace Award from the Wellness Council of America, which recognizes our commitment to wellness in the workplace. The organization includes 27 retail stores and training centers in communities from Manitowoc to La Crosse, 24 human services programs, a unique shopping experience at its Appleton outlet store, plus online shopping at, a women’s apparel website, and It offers four Donation Express sites and 10 convenient donation bins throughout the Fox Cities. Goodwill NCW is a Platinum Level member of, the world’s largest source of nonprofit organization information. Visit


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