These shoes can take your outfit from day to night with ease. For a party look, wear your black leather skirt with a pair of strappy heels and a fitted top of your choice.

3. Ankle Boots

If you’re looking for the best shoes to wear with a pencil skirt in the colder months, ankle boots are definitely the way to go. Not only will they keep your feet nice and warm, but they’ll also add a touch of edge to your look. For a chic alternative look, pair your graphic tee with a classic pencil skirt and your choice of ankle boots.

Alternatively, you can switch ankle boots for flat or heeled combat boots if that’s more your style.

4. Sneakers

If you’re searching for the best shoes to wear with a pencil skirt but you don’t want to sacrifice comfort, then go for flat shoes like a pair of sneakers. You can find some really cute and stylish pairs that will look great with just about any skirt.

Make sure to wear clean, sleek sneakers, unless you’re going for a particularly casual aesthetic. Complete your outfit with a coat or a black leather jacket.

5. Knee High Boots

Knee high boots are the perfect choice if you want to make your look a bit sultrier. Tall boots can be worn with skirts of all lengths, and they’ll keep you warm in the colder months. (Pro tip: if you’re pairing these with a pencil maxi skirt, make sure there’s a high slit to show off your boots!)

For a cute fall look when going out shopping, wear a black leather pencil skirt with a pair of black suede boots. Complete the look with a chic sweater on top, or a long-sleeve blouse of your choice.

6. Flat Sandals

If you want the best shoes to wear with a pencil skirt during the summer months, flat sandals are the way to go. Not only will they keep your feet cool, but they can also add a touch of glam, especially if you’re opting for a pair of metallic sandals, or a designer pair like the Miller sandals from Tory Burch.