I've Done the Research—These Are the Best Boots to Wear With Mini, Midi and Maxi Dresses

I’ve never been a trouser kind of girl—aside from having given into the easy appeal of jeans, that is. Instead, you’ll find my wardrobe is dominated by one thing: dresses.

Being curvy and petite, dresses are the item I feel most confident in, and I’ve garnered quite the collection of them over the years. However, when it comes to winter, I always find myself at a loss. During the summer months, I’ll style them with slip-on tan sandals or black minimal mules but, when the temperatures drop, I seem to struggle to find the right footwear to pair with them.

Sylvie wears a knitted mini dress and simple black boots.

Boots are, of course, essential at this time of year, but I’ve always found it difficult to decide which boot iterations look best with mini, midi and maxi dresses respectively. So, I set about rectifying that.

Having spent large amounts of time trawling through the social media ether, I can say with complete certainty that I’ve found the combinations that work best. From maxi and mini to lace-up and Western, keep scrolling to discover which boots to wear with mini, midi and maxi dresses once and for all.

The 9 Best Boot Styles to Wear With Mini, Midi and Maxi Dresses for Winter 2024:

DRESS TYPE: MINI

Thanks to the space between the hem and your boots, minidresses loan themselves well to more ornate boot styles, such as lace-up fronts, as well as more directional silhouettes, including Western iterations. That said, they can look incredibly sexy worn with thigh-high boots.

Shop the Best Boots to Wear with Mini Dresses:

1. LACE-UP

2. OVER-THE-KNEE

3. WESTERN

DRESS TYPE: MIDI

Typically speaking, there are few boots that won't go with midi dresses. But, in our opinion, the strongest pairing is slouchy knee-high boots; particularly when you match them to the shade of your dress. As far as flats are concerned, a chunky moto boot will also work—the midi length will stop them from looking frumpy. If you're petite or desire a little extra height, why not consider an on-trend platform sole shoes.

Shop the Best Boots to Wear with Midi Dresses:

1. BIKER

2. SLOUCH

3. PLATFORM

DRESS TYPE: MAXI

Maxi dresses can often feel as if they're swamping you, which is why we recommend donning pointed-toe heeled boots, which will help to elongate your frame. Often floaty, we also suggest trying a beige or suede style for a softer finish than typically heavy leather.

Shop the Best Boots to Wear with Maxi Dresses:

1. POINTED-TOE

2. BEIGE

3. SUEDE

This post was originally published at an earlier time and has since been updated.