What to Wear With Maxi Skirts in Fall and Winter

Whether you're looking for styles that will work with full, flowing maxi skirts or maxis of the more form-fitting variety, you'll probably find something on this list that is already lurking in your closet. If not, you'll at least be armed with some helpful tips for your next shoe-shopping trip.

Flat Boots

I can't stress enough how well flat boots work with maxi skirts. In fact, they work so well, that the shaft height and style of the boots barely even matter; knee high, over-the-knee, ankle, lace up, side zip, pull-ons all work great, as do casual, grunge-styled boots; equestrian-styled boots, and even military- and Victorian-inspired styles.

But as with most things in life, there are a few exceptions. Some of them really shouldn't need pointing out. For example, you wouldn't dream of pairing a pair of rain boots with a pretty maxi skirt, no matter how casual it was. Other obvious no-nos include desert boots, most winter boots, and anything that looks too "outdoorsy."

Check out a few of my favorite flat boots to wear with your maxi skirt, available on Amazon.com: 

• Nine West Women's ​Doloris Suede Boot
• FRYE Women's Melissa Button Boot
• Sperry Top-Sider Victory Lap Chelsea Boot

Heeled Booties and Ankle Boots

As I said above, the full-length of maxi skirts means that the shaft height of your boots barely matters — but still, booties and ankle boots go with maxi skirts and dresses like peanut butter goes with jelly.

For the most cohesive look, try choosing a pair of boots that extend beyond the hem of your skirt, so that no leg is showing. If you prefer a pair of booties, and your skirt isn't quite long enough to cover the tops of them, you can always add a pair of tights for a look that's ideal for fall and winter.

Check out a few of my favorite pair of heeled booties and ankle boots on Amazon.com: 

• FRYE Ciera Shootie Boot
• Dolce Vita Hastings Bootie
• Cole Haan Abbot Ankle Boot

Flat Shoes With Maxi Skirts

Wearing flats with maxi skirts is a bit tricky. You want to avoid anything that might look too much like you're wearing a pair of slippers, and at the same time, there are certain shoe styles that are far too masculine for the femininity of a maxi skirt or dress.

The styles that are easiest to work with are classic ballerina flats, and pointy- or open-toed flats. To maximize your chances of success, look for very simple styles that show a generous amount of foot, and also look for styles with subtle or classic accents, like kiltie detailing, chic vamp brooches, or contrasting toe caps.

Check out my favorite flats to wear with your maxi skirt, available on Amazon.com: 

• Corso Como Merla Flat
• Delman Sade Flat
• Dolce Vita Adalynn Ballet Flat

Maxi Skirts With High-Heeled Pumps and Shoes

Round toed pumps don't always work as well with maxi skirts as styles with pointy, almond, or open toes. The reason for this is because they generally don't offer enough contrast from the skirt itself.

One way to counter this is to look for round-toed pumps that are cut very low (in other words, they'll show a lot of the top of your feet). Another option for cooler weather is to use tights to bridge the gap.

In contrast, fashion clogs and mules that have rounder toe boxes work great with really long maxis, because the top of the foot is completely covered by the shoe. The only thing you have to watch for with open-backed shoes is leaving your heels exposed, which generally isn't a great fall or winter look. In some cases, it's never a good look. To avoid this being an issue, you simply need to find a maxi skirt that is long enough to cover the back of your feet in your chosen mules or clogs.

Check out a few of my favorite fashion clogs and mules available on Amazon.com: 

• Kate Spade New York Cala Clogs
• Seychelles Slide Pump
• MIA Elsa Slip-On Mule

Heeled Boots

Just like their shorter counterparts, tall boots with high heels work wonderfully with maxi skirts and dresses. If your skirt is a simple shape and a solid color, let the boots dictate the tone of the outfit. If your maxi has a strong personality on its own, then opt for simpler, streamlined boots that will flatter the skirt, instead of competing with it.

Check out a few of my favorite heeled boots to pair with your maxi skirt, available on Amazon.com: 

• Steve Madden ​Lauuren Boot
• Vince Camuto Sidney Riding Boot
• Jessica Simpson Slouch Boot

For shoe styles that will take your maxi skirts and maxi dresses into warmer weather, be sure to check out the first part of this article: What to Wear With Maxi Skirts in Spring and Summer.