Skinny, ankle length pants are fun, chic and elegant to wear for work and casual.  In order to get the most out of them you want to have the right shoes on hand.  Unfortunately, depending on where you live, skinny ankle pants can have a short shelf life.  You probably won’t want to wear them on the coldest days of the year.  However, you can wear them well into the fall if you have the right shoes.  Below are five looks using the best shoes to wear with ankle length skinny pants once you welcome in the cooler weather.

The Best Shoes to Wear with Ankle Length Skinny Pants

#1- Moccasins and Loafers

best shoes for ankle length skinny pants Moccasins and loafers are super trendy and can be very stylish, however, they often work better in theory than they do in reality.  Every time I pick up a pair of driving loafers at the store I covet them.  Yet, once I try them on, they look just don’t look good.  In order for these types of shoes look right and not too masculine I think a little ankle showing helps.

Take how I styled these Tod’s metallic driving loafers with a pair of blush Boden skinny ankle pants.  It’s an updated preppy look that works well with this J. Crew chambray shirt, navy bag from MICHAEL Michael Kors and coral studs from MARC by Marc Jacobs.

#2- Ballerina Flats

Shoes for Ankle Length Skinny Pants Ballerina flats are a pretty obvious choice to wear with skinny ankle pants.  Don’t pack these shoes away once the weather cools off.  Use them with more autumnal looks to create a chic transitional outfit like I did here using this pair of red flats from Cole Haan with these navy ankle pants from J. Crew and sweater and shirt combo top from French Connection.  To finish the look, I used this cognac Dooney Bourke satchel, geometric hoops from Max & Chloe and Bauble Bar bangle.

#3- Oxfords

shoes for ankle length skinny pants Oxfords are fantastic with skinny ankle pants for the same reason that moccasins and loafers are, they look more feminine when a little ankle shows.  Plus, oxfords can easily take these  shorter pants well into the fall.  In this look, I styled these Franco Sarto oxfords with a pair of Theory ankle pants.  For a cool weather look, I added this Alice + Olivia sweater and finished the outfit with a burgundy bag from Rebecca Minkoff, leather wrap bracelet from Le Mer and drop earrings from Stella & Dot.

#4- Heels

shoes for ankle length skinny pants Don’t discount heels when wearing your skinny ankle length pants.  Any heel height will work.  The benefit of wearing heels with these types of pants is they lengthen your legs.  Not only does this help balance out the shortening effect that cropped pants can have, but elongating the legs can make your hips and thighs look narrower.

In this outfit, I used these suede platform pumps from Calvin Klein with ankle pants from Reiss.  For a dressier look, I added this red blouse from Zara, gold and black clutch BCBG and layered necklace from Ann Taylor.

#5 Ankle Boots

shoes for skinny ankle length pants To really get the most out of your skinny ankle pants try wearing them with boots.  The best boot styles are booties and styles like chelsea boots because, unless you ankle cropped pants are super skinny around the ankles, it will be tough to wear them with boots that require you to tuck  in the legs of your pants.  Instead, boots that fit under the pants will work best.

In this outfit, I styled these skinny, ankle length cargos with Lucky Brand chelsea boots and, for a weekend look, layered this coral top from LOFT under this easy camel cardigan from Theory and accessorized it with this leaf necklace from Modcloth and handbag from Frye.

Summer shoes to wear with ankle length skinny pants

Throughout the rest of the summer, don’t forget about your wedges and sandals as great shoes to wear with you skinny ankle pants.  As the summer winds down, and cooler weather comes around, look to these additional styles to create some fantastic outfits.