How to Wear Ankle Boots With a Dress

Ankle boots go with most dresses if you watch the gap between the hem and the top of the boot. A dress that ends above the knee or at mid-calf leaves a gap that looks deliberate; one that stops just below the knee can make your legs look shorter, unless tights in the boot's color close the gap.

Below: which dresses suit boots, the main kinds of ankle boots, what goes on your legs, and how to dress the look up or down. Each product is an Amazon listing, described from its listing; none was worn for this page.

Which dresses go with ankle boots

Dresses with boots look best when the dress has some weight to it. Knits, wool, corduroy, denim and flannel all sit well with a boot. Floaty chiffon can look mismatched next to a chunky sole, though a sleek heeled bootie handles it.

• Mini: the easiest length for any ankle boot. Add opaque tights once it's cold.
• Above the knee: the same, and a heel makes your legs look longer.
• Just below the knee: the hardest length. Wear tights the same color as the boots so the gap disappears.
• Midi: works well; see below.
• Maxi: the hem covers the shaft, so any ankle boot goes, and it's mostly there for warmth.

A midi dress with boots

A midi dress with boots works when the hem and the boot don't meet at the same point on your calf. A calf-length midi over a heeled ankle boot leaves a strip of leg or tights that looks intentional.

The MEROKEETY dress is an off-shoulder ribbed bodycon midi that the listing gives as about calf length, in viscose, polyamide and polyester, from X-Small to X-Large; machine wash. Other ways to wear a knit dress are in sweater dress outfits.

The main kinds of ankle boots

Heeled booties with a dress

Booties with a dress are the dressiest ankle boot. A block heel is easier to walk in than a stiletto and lifts the line of a midi.

The DREAM PAIRS boots are faux leather on a 3-inch block heel with a latex insole, in sizes 5 to 11, and the listing gives the shaft circumference as 10.5 inches. The Lovee Cosee pair has a square toe, a 3.5-inch angled block heel and a side zipper, in sizes 6 to 11.

Chelsea boots with a dress

Chelsea boots with a dress make a weekend outfit: usually flat, slip-on, with stretch panels at the sides. They suit a knit midi, a shirt dress, or a slip dress with a sweater on top (how to wear a sweater over a dress shows how).

The Athlefit boots are slip-on faux leather with a lug sole and a 4.2-inch shaft, in sizes 5.5 to 11. A lug sole looks chunky, so pair it with a dress that has some weight rather than thin satin.

Sock boots

Sock boots have a stretch-knit shaft that hugs the ankle, so the line from hem to shoe stays slim. They're the neatest choice with a fitted dress. The CUSHIONAIRE Neely booties have a stretch-knit upper on a block heel with memory foam, in sizes 6 to 11, with wide widths listed too.

Tights, socks or bare legs

In cold weather, tights in the same color as your boots make your legs look longer and hide the line at the ankle. Black opaque tights with black boots are the easy default. The no nonsense tights are 90 denier, super opaque, with a control top, in Small to XX-Large; the listing says the waistband is no-roll and says hand wash only.

Bare legs with ankle boots suit early fall and late spring. A thin sock peeking over a Chelsea boot can look deliberate with a casual dress; keep it one plain color. On freezing days, fleece-lined tights are the warmer layer.

Ankle boots with a dress, casual to dressy

• Weekend: Chelsea boots, a knit or shirt dress, a denim or utility jacket.
• Office: heeled booties, a midi work dress, opaque tights and a blazer.
• Dinner or a party: sock boots or heeled booties with sheer black tights and a fitted dress.
• A fall wedding: best kept to a casual or barn wedding, with a sleek heeled bootie. For anything dressier, wear heels, and for a burgundy dress, what color shoes to wear with a burgundy dress has the options.