How to Style Ankle Boots With Long Skirts (Modest Outfit Ideas)

Ankle boots are the shoes I reach for most once the weather turns. They're warmer than flats, easier to walk in than heels, and they make a long skirt look current instead of fussy. The tricky part is the gap between the hem and the boot. Get that right and almost any long skirt works.

Here's how I pair ankle boots with midi and maxi skirts, and the combinations I wear on repeat.

Pick the right ankle boot

• Shaft height. A boot that ends just above the ankle bone is the easiest with long skirts. Very low booties can look like a gap with no purpose.
• Heel. A low block heel or a flat lug sole is comfortable all day and looks right with fuller skirts. Slim stiletto booties feel dressier and suit sleeker skirts.
• Toe shape. A soft almond or round toe is the most versatile. A very pointy toe is chic but reads more formal.
• Material. Smooth leather looks polished, suede feels softer and warmer, and a weatherproof leather or rubber boot is the practical pick for rain and slush.
• Fit. Choose a shaft that sits close to the ankle. A wide, gaping shaft makes the hem flare out awkwardly.

Which skirt lengths work best

Maxi skirts. The easiest match. When the hem falls to the ankle or just above, the boot almost disappears and the skirt does the talking. Denim, knit, tiered and pleated maxis all look great.

Long midi skirts. A hem at mid-calf leaves a few inches of leg showing above the boot. Fill that space with opaque tights in the same shade as the boot, and the outfit looks long and seamless.

Classic midi skirts. A hem just below the knee leaves the biggest gap. It still works with matching tights and a slightly taller boot, but a knee-high boot is often the better choice here.

Tights make it work

Tights are the secret to a clean ankle boot outfit with a midi.

• Match the tights to the boots. Black tights with black boots, brown with brown, grey with grey. It creates one long line and makes you look taller.
• Go opaque. Sheer tights with chunky boots can look disjointed. A 60 to 80 denier tight looks smoother.
• Try a tonal match to the skirt. A navy skirt with navy tights and navy suede boots is very elegant.
• Fleece-lined tights are worth it on cold days and still look like regular opaque tights.

Skirt shapes and the boots that suit them

• A-line and flared skirts. Pair with a sturdier boot, like a lug sole or a block heel, so the shoes balance the volume.
• Straight and column skirts. A sleeker boot with a slim heel keeps the line long.
• Tiered and prairie skirts. Suede western-style booties or simple brown leather boots feel natural and relaxed.
• Pleated skirts. A smooth leather bootie in black or dark brown looks polished and lets the pleats move.
• Denim skirts. Almost anything goes. Brown suede, black leather and combat-style lace-ups all look right.
• Satin and silk skirts. A sleek leather bootie with a low heel dresses the outfit up while keeping it wearable.

Colors that always work

• Black. The most versatile. It works with grey, navy, camel, plaid and every dark skirt.
• Chocolate and cognac brown. Warm and soft with camel, cream, rust, olive and denim.
• Taupe and grey suede. Lovely with cream, blush and light grey for a gentle, tonal look.
• Burgundy. A fun accent with navy, grey or black outfits.

7 ankle boot outfits I wear on repeat

1. Weekday errands. Long dark denim skirt, cream cable knit, brown suede ankle boots, a camel coat.

2. Office. Grey pleated midi, black turtleneck, black opaque tights, black leather boots with a block heel.

3. Rainy day. Navy A-line maxi, striped long-sleeve tee, waterproof black lug boots, a trench coat.

4. Shabbos lunch. Champagne satin midi, ivory blouse, nude tights, taupe suede booties with a low heel.

5. Fall weekend. Rust tiered maxi, denim jacket, cognac leather boots, a crossbody bag.

6. Cozy and tonal. Oatmeal knit midi skirt, matching sweater, oatmeal tights, light brown suede boots.

7. Evening out. Black velvet midi, black blouse, sheer black tights, sleek black booties and gold earrings.

Common mistakes to avoid

• A bare gap of leg. With a midi and ankle boots, a few inches of skin breaks the line. Add tights that match the boots.
• A slouchy, wide shaft. It catches the hem and looks messy. Pick a boot that hugs the ankle.
• Boots that are too heavy for a delicate skirt. A thin chiffon skirt can look overwhelmed by a huge combat boot. Choose a sleeker bootie.
• Hems that drag. A maxi that hits the ground gets wet and dirty with boots. Hem it to just above the ankle.

Caring for your ankle boots

• Spray suede and leather with a protector before the first wear.
• Wipe off salt and mud as soon as you get home, and let wet boots dry away from heat.
• Condition smooth leather a few times a season so it doesn't crack.
• Use a suede brush to lift the nap and remove marks.
• Store them with boot shapers or rolled paper so the shafts keep their shape.

The bottom line

Ankle boots and long skirts are an easy, modest pairing for fall and winter. Pick a boot that hugs the ankle, wear it with maxi skirts as is, and add matching opaque tights when you wear a midi. Balance full skirts with sturdier boots and sleek skirts with slimmer ones, and you'll have an outfit for almost every day of the week.

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