Dresses with boots are the easiest way to keep wearing dresses as the weather turns. These four pairings match knit dresses with knee boots, slips with ankle boots, printed midis with riding boots and shirtdresses with slouchy boots. There are four more boots to start with, from lug soles to western.
Dresses With Boots, Four Fall Pairings
Four Boots to Start With
A dress with the right boot takes you from September to the first frost without starting your wardrobe over. Start with the boot, since it decides how the dress reads. Jimmy Choo's chocolate lug-sole biker boots, Christian Louboutin's black heeled Kate Botta knee boots, Saint Laurent's brown suede Jill ankle boots and Gabriela Hearst's black embroidered western Capitana boots cover four very different moods.
Knit Dress, Knee Boots
A knit dress with a knee boot is warm, simple and very hard to get wrong. Ruohan's beige ribbed Lomma maxi in yak, cashmere and wool pairs with Jimmy Choo's black leather Agathe knee boots, and Gabriela Hearst's burgundy belted ribbed-knit Tenes midi goes with Victoria Beckham's black Maverick knee boots. The boots should meet the hem or disappear under it, never stop just short.
Slip Dress, Ankle Boots
An ankle boot takes a slip dress out of evening and into the office. Joseph's black silk-satin Cloe slip pairs with Manolo Blahnik's dark brown leather Vivecal ankle boots, while Lauren Manoogian's grey paneled satin slip goes with Isabel Marant's black suede Eldra ankle boots. Add a chunky knit or a leather jacket over the top when it gets cold.
Printed Midi, Riding Boots
A flat riding boot grounds a printed dress and makes it feel sporty. La DoubleJ's magenta printed silk-georgette midi goes with Polo Ralph Lauren's black leather knee boots, and Dries Van Noten's long-sleeve floral-print crepe dress pairs with Aquazzura's black leather Ride boots. Keep the rest plain and let the print carry the look.
Shirtdress, Slouchy Boots
A shirtdress is structured, so a slouchy suede boot relaxes it. Marrakshi Life's green striped cotton Oxford Long Shirt dress pairs with Khaite's brown slouchy Clive suede knee boots, and Emilia Wickstead's charcoal Prince of Wales checked Jody shirt dress goes with Aeyde's dark brown suede Medea knee boots. Roll the sleeves and leave a few buttons open.
Our honest take
Dresses with boots are the smartest way to stretch a summer wardrobe into fall, because the dress stays the same and only the shoe changes. If you take one thing away, let it be that the boot should relate to the hem, with knee boots under midis and maxis and ankle boots with slips that show a little leg. We would skip boots with very high platforms or heavy embellishment for these pairings, since they fight with the dress instead of finishing it. A flat riding boot and a suede ankle boot will cover most of the dresses you already own. Add tights once the temperature drops and keep going well into winter.
