Transitional Boots: How to Wear Boots with Dresses

As we move between seasons, it can be hard to keep up when it comes to style. September brings weather that seems to change from blazing sunshine to driving rain in a gust of wind. While the mornings may start off chilly, don your fluffy jumper too early in the season and you’re breaking a sweat by mid-afternoon. When everything is in flux, you need balance. 

Bring on boots and dresses! The perfect style to counter your summer dresses and skirts, the boots and dress combo is so simple to execute, yet it will garner a compliment or two wherever you go. 

Women's Boots Sale

Whether you’re wondering how to wear ankle boots with dresses or how to style your knee-high boots this September, we’ve collected our favourite looks from across platforms to inspire your transitional style.

Looking to get your hands on boots to go with dresses asap? Our women’s boots sale will see you instantly take advantage of this simple transitional style mantra for so much less. 

How to Wear Boots with Summer Dresses

While autumn may be just around the corner, it’s not quite time to put away your summer dresses yet. 

@ladywritesblog shows just how to pair ankle boots with a dress, opting for a colourful floral print mini dress with neutral-toned boots. 


Neutral tones serve the transitional period well. As light as a summer breeze, neutrals also look forward to the tones that autumn brings. Consider neutral ankle boots an investment piece. Not only will they serve you through this season, they’ve got everything else covered too.  

A block heel boot is a must-have style that will (quite literally) elevate your transitional ensembles, giving them a clean, well-considered feel. Not to mention block heels will carry you, from dawn to dusk, through every occasion dress code with ease.


How to Wear Biker Boots with Dresses

Oozing easy, sleazy sophistication the biker boot and dress combination conjures images of indie rock stars and festival style. 

To style your biker boots with a dress, cinch your middle with a belt that matches your leather boots to bring the look together. When it comes to styling with a skirt, take a note from @stylishmumjournal book and pair a patterned skirt with a printed tee, and of course some ultra-cool sunnies. 

How to Wear Chelsea Boots with Dresses

Chelsea boots offer a simple pull-on style in a casual silhouette, steeped in heritage. Harking back to the Victorian era, Chelsea boots have stood the test of time. Their long history has also led to their reinvention in increasingly new and exciting ways. 

@halliedaily styles her chunky off-white Chelsea boots with a tea dress and bright green handbag, signed off with a bucket hat and sunglasses to support the casual charm of this boot and dress combo.

Speaking of green, @heartfelthunt takes the updated chunky Chelsea a step further. Styled in a tall silhouette and based on an ultra-chunky sole, these Chelsea boots have got us feeling green with envy. 

When looking for a dress to wear with chunky boots, consider offsetting the impact of your boot’s dramatic silhouette with a ditsy pattern, such as florals or polka dots. @heartfelthunt keeps any potential chill at bay with a fuchsia cardigan draped daintily over her shoulders. 

How to Wear Knee-High Boots with Dresses

As the days grow shorter, the countdown to knee-high boots begins! There’s nothing quite as classic as a pair of black leather knee-high boots, and @stylishmumjournal takes them in her stride. 

 Providing a masterclass in how to style a dress with knee-high boots, @stylishmumjournal pairs her chunky knee-high boots with a short shirt dress and blazer, balancing her hemlines with the tops of her boots. Add a belt and matching black handbag… dare we say this is the perfect transitional look? 

When it comes to wearing tights with dresses and boots, why not switch up your style game by introducing a pair of patterned tights to the mix? We recommend completing your boots and dress combination with a pair of barely-there tights patterned with delicate spots. 

Women's Boots Sale