There’s one thing we love most about the cooler season and that’s boots! In a range of colours, shapes, and styles; women’s boots make an absolutely essential choice for autumn and winter because they present limitless outfit options for virtually every occasion.
While the sun may be setting on summer, now’s a better time than any to bring out the pieces in your wardrobe that have spent the last year in hibernation. So, if you’re looking for ideas on the best boots to wear with dresses and skirts, you’re in the right place!
We’ve put together a need-to-know dress and boots style guide to help you put together chic and comfortable outfits in a matter minutes. From classic knee-high boots to casual calf length boots, biker silhouettes and Chelsea boot styles, it’s time to meet our favourites and how you’ll find us wearing them this season …
There are a variety of outfit combinations when it comes to wearing dresses and boots, with so many boot options out there it can feel overwhelming choosing something that fits well, looks good, and of course feels comfortable too!
By following a few simple style rules, you can create easy outfit combinations that you’ll be able to throw on through the cold seasons – and even the warmer ones too!
First thing’s first, you need to pick out a dress that’s suitable for the occasion and find the boots that will match your outfit. It’s important to pay attention to where the hemlines of your dresses sit and ensure that the cut of your boots complement this, the key is to lengthen your silhouette, so ankle boots and knee-high boots are the classic silhouettes to work with.
The beauty of wearing boots is that they are so versatile, so they’ll work just as well with tights as they will without. Whether you’re wearing knee high boots or ankle boots, the trick to cold weather dressing lies with layering, so keep things cosy and casual with a pair of woolly tights or get smart with a pair of sheer tights.
As for the summer months, wearing a calf length dress or a skirt with a pair of heeled ankle boots and bare legs makes the perfect sun-ready outfit. Styles like a long floaty dress or a pleated skirt are an elegant choice for ladies who don’t like to flash too much flesh but want to remain cool (and stylish) in the heat.
Short boots, like ankle boots and Chelsea boots are perfect for wearing with dresses through every season, whether it be winter or summer. Ankle boots are perhaps the most popular style for wearing with dresses as their short silhouette will elongate the appearance of your leg.
Flat boots like Chelsea boots are a real all-rounder where versatility is concerned, considered the most classic style of ankle boots, they work well with knee length dresses and skirts, plus they’re easy to slip on thanks to their stretch side panels and flexible to step you through the day with ease.
For a smarter look, go for a dress with a longer length, preferably down to your ankle, and wear either heeled ankle boots or knee-high boots.
By layering delicate hemlines and ditsy floral prints you can create an easy and elegant look.
Use a belt or a tie across your waist to break up the long length of the dress and accentuate your figure, this will work especially well if you’re wearing a dress with a print or pattern as this can overpower the general shape of your dress.
Practical, stylish, and endlessly versatile if there’s one footwear style to invest in for autumn and winter, it’s a pair of chunky boots. A go-to style that that will complement an array of outfits for smart and casual occasions, they’re surprisingly comfortable, so you can wear them pretty much everywhere!
Boots with exaggerated soles have become a real style favourite over the last year, they look just as good with your everyday jeans as they do with your dresses and skirts, with tights and without. Chunky boots are great for adding a little edge to your looks, so wear a pair of chunky hiker boots with a floaty floral print dress and thick denier tights to change up your smart looks, if it’s chilly throw on a tailored woolly coat.
Not ready to give up your summer dresses just yet? No problem! A pair of biker boots will make the perfect replacement to your sandals, wear your colour-block dresses with a pair of sheer patterned tights or opt for a high denier tights with mid-length ditsy print dresses.
Biker boots are built to be bold, originally worn for practicality they have slowly become a favourite style in women’s wardrobes, especially teamed with dresses – whether long or short. Popular for a reason they’re a great option for comfort and they’ll keep you warm and provide protection against the rain and snow.