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

There are some fashion combinations that just inherently go together better than others. Boots and dresses are one of those pairings that seemingly click without having to put much thought into styling a look. But what are the boots to wear with mini, midi and maxi dresses? When there are so many variables to consider—specifically the hem length and where on the leg you'd like the boot to stop—this is an important question to consider.

Well, at least that is something I've been pondering lately. I’ve never been a trouser kind of girl—aside from having given in to the easy appeal of jeans, that is. Instead, you’ll find my wardrobe is dominated by 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.

Style Notes: Paris-based stylist Sylvie Mus wears a knitted mini dress and simple black boots.

Boots are, of course, essential in any wardrobe irrespective of what 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, and it appears I'm not the only one with this thought plaguing them

"When it comes to boots and dress outfits, I find myself swearing by a few self-appointed rules," Who What Wear SEO Writer, Ava Gilchrist, says. "Mini, midi and maxi dresses will all be complemented by boots with heels, however, I often find shorter styles and flat shoes a slightly harder silhouette to pull off, simply because of how much leg is exposed without anything to elongate it. These "rules" might seem random to you, but to me, these are the proportions that I find the most appealing."

Having spent large amounts of time trawling through the social media ether, I can say with complete certainty that these the combinations work best. So without further ado, keep scrolling to discover which boots to wear with mini, midi and maxi dresses once and for all.

The Best Boot Styles to Wear With Mini, Midi and Maxi Dresses

Dress Type: Mini

Style Notes: Thanks to the space between the hem and your boots, mini dresses lend themselves well to more ornate boot styles, such as the ever-popular biker boot style with intricate buckle and strap details, as well as more directional silhouettes, including Western iterations. That said, they can look incredibly sexy when worn with stiletto heel knee-high boots. (Just ask Emily Ratajkowski and her countless bodycon dress and knee-high boot off-duty looks!)

Shop the Best Boots to Wear with Mini Dresses:

1. Cowboy Boots

2. Biker Boots

3. Stiletto Heel Knee-High Boots

Dress Type: Midi

Style Notes: Typically speaking, there are few boots that won't go with midi dresses. But, in our opinion, the strongest pairing is a classic flat-sole riding boot. As far as flats are concerned, a chunky lace-up combat boot will also work. However, if you want your look to read a little less punk and slightly more pretty, there are plenty of chic lace-up flat shoes out there from the likes of The Row and Bottega Veneta.

Shop the Best Boots to Wear with Midi Dresses:

4. Riding Boots

5. Mid Calf Boots

6. Lace Up Boots

Dress Type: Maxi

Style Notes: Maxi dresses can often feel as if they're swamping you, which is why we recommend donning pointed-toe shapes, which will help to elongate your frame. Of course, given the length of the dress, there's some flexibility on where the boot can sit on your leg, meaning that you can reach for more casual styles like a Chelsea Boot without worrying about feeling like you're cutting off your body at an odd place.

Shop the Best Boots to Wear with Maxi Dresses:

7. Chelsea Boots

8. Ankle Boots

9. Knee-High Boots