EVELYSS / Guides / Fashion Sense

What Jeans to Wear With Ankle Boots (Skinny, Straight, Wide-Leg and Flare)

“Ankle boots are never the problem. The trouble lives in the two inches between the hem and the boot, and once you decide what happens there, every pair of jeans you own starts working.”Her take

The one rule: decide where the hem meets the boot

Every good jeans-and-ankle-boot outfit falls into one of three choices. The hem goes inside the boot, the hem ends just above the boot with a little skin or sock showing, or the hem goes over the boot and covers the shaft completely.

What doesn't work is the in-between: denim that lands on top of the boot and folds into a crumpled ring. Check yourself standing and sitting, because hems ride up when you sit.

Skinny and slim jeans

These are the easiest. Either tuck them fully into the boot or roll them once so the hem ends half an inch above the boot top. Tucking works with boots that have a slimmer shaft; with a wider shaft, the gap looks like a funnel, so roll instead.

A pointed or almond toe and a small heel make this look sharper. A chunky lug sole works too, but keep the jeans close-fitting so the boot is clearly the focus.

Straight-leg jeans

Straight legs are the most versatile pairing. The ideal length is cropped to the ankle bone, so the hem sits right at the top of the boot or a sliver above. If your pair is longer, cuff it once or twice, about an inch each time, and keep the cuff neat.

Avoid tucking straight jeans into ankle boots. The extra width bunches at the boot opening. If the jeans are long and you don't want to cuff, wear them over a boot with a slim ankle so the hem drapes cleanly.

Wide-leg, bootcut and flared jeans

These go over the boot, always. The hem should fall long enough to cover the shaft and reach the top of the foot, ideally a half inch to an inch off the floor at the back when you wear the boots. Have them hemmed while wearing the boots you will wear most.

A boot with a heel, even one or two inches, keeps a long hem from dragging and lets the leg fall straight. A narrow-ankle boot fits under a wide leg without making the hem bulge.

• Wide-leg: hem covers the boot, toe just showing.
• Bootcut and flare: hem breaks on the top of the foot.
• Cropped wide-leg: this is the exception; the hem ends mid-calf and you show the whole boot plus a little ankle or a sock.

What about socks?

If any gap shows between jeans and boot, decide what fills it on purpose. Bare ankle works in mild weather. Otherwise wear a sock that matches the boot or the jeans so the line continues, or a fine ribbed sock in a deliberate contrasting color such as cream with brown boots.

Sports socks with a visible band, or a sock that matches neither, are what make the gap look accidental.

Which boot color goes with which wash?

Black boots suit black, gray and dark indigo jeans for a long, unbroken line. Brown and tan boots look warmest with mid-blue and light washes and with ecru denim. Suede in taupe or chocolate softens dark jeans. For the longest-looking leg, keep boot and jeans close in tone.

Questions people ask

The takeaway

Tuck, crop, cuff or cover: pick one for the hem, never let denim land on the boot, and hem wide legs while wearing the boots you'll actually wear.

Read next