How To Wear Boots With Dresses

If there’s one thing that makes winter worthwhile it’s that we get to unleash our boots! For us ladies, boots can hold a certain special place in our hearts. Whether it’s the versatility of a boot that suits everything, how snug they make our tootsies or just the look, we love boots!

And if you’re not all about the trousers and are looking for boots to wear with dresses, then allow us to help!

Here’s our quick style guide for wearing boots with dresses in 2023.

The first rule, and it’s a truly glorious one, is that, nowadays as with much of fashion, there really are no rules! Gone are the days of strict dogma around what you can and can’t pair and we’ve moved much more to an age of allowing you to be you! We can now much more wear what we want with what we want and embrace our own sense of style.

And in this mould, boots are an absolutely timeless wardrobe investment for year round dressing to be paired with all sorts of outfits for all sorts of occasions.

That being said, we’d generally suggest that, if you’re pairing boots with a dress, opaque tights, plain or ribbed, give a flattering look. Or, depending on the outfit you’re matching to, a patterned tight could complete the look. Summertime festival? Ditch the tights altogether and show off your legs!

Patterns or block colours can look amazing with boots and we are very lucky right now in that prints and florals are very on trend, so don’t be afraid to mix it up. You can be confident that you’ll be dressing in style, whatever your choice.

As well as making your dress the highlight, don’t be frightened to make your boots the highlight, with boldly coloured boots like Bayeux, Crawley or Taipei.

When pairing ankle boots with dresses, consider that the ankle of an ankle boot tends to be more fitted to the leg than say a biker boot. This means that you can pretty much wear ankle boots with any dress length, being limited by only the amount of leg you wish to show.

All of our boots are wide and deep fitting, with many of our boots available in 6V variable width fitting to accommodate feet up to (8E) EEEEEEEE width.

Many are arthritis, diabetes or bunion friendly and suitable for swollen feet or feet that swell.

Inside zips work alongside other fastenings like buckles or laces to allow you to set your style to the fit or the look that you want then simply use the zip for easy foot access.

Aberdeen is ankle boot with wedge heel that adds that extra bit of height to lengthen the legs and is equally at home with shorter or longer dresses, while Goldcrest looks fab with dark opaque tights and a shorter dress in matching colour scheme.

Casual ankle boot Unite looks just fantastic with a mid-length dress; the casual leather style sitting on our Bumper Sole can be dressed up or down as required, while Santa, a sporty ankle boot with stretch panels looks super cute with coloured dress & black tights.

All styles above except Unite are lace-up styles with inside zips so you can adjust the fitting to your comfort or style then simply use the inside zip for easy access. Simply loosen or tighten the laces as required for the best fit for you then use the zip!

Biker boots are longer and tend to be wider at the top than ankle boots, so create a different silhouette.

We’d recommend a biker boot with a flowing maxi-dress or above the knee dress although, as you can see from the photographs below, a handkerchief hemline can look fab too.

We’ve paired biker boot Reef with a long flowing dress and tights colour matched to a plain black top and Bayeux in denim with a light floral patterned dress or in lilac with a beautifully autumnal patterned dress.

You’ll also find more florals complementing the colour splash on new biker boot Rainbow.

The good news about knee high boots is that, well, they can really be worn with anything! Paired with a maxi-dress they look stunning, below the knee, above the knee or even a mini-skirt! Of course they also look great with jeans for an equestrian or smart casual look. Knee high boots really do offer the versatility to be worn with anything.

1. We love pairing this long denim dress with Tasman, a stylish and practical knee length boot that has an adjustable stretch back panel for calves, a stylish 1½" low heel, grippy rubber outsole, inside zip for easy access, round shape toe and two removable "air-cushioned" insoles to create extra depth or for the insertion of orthotics.

2. Chelmsford is a popular knee high boot in black or brown that we think looks great with this below-the-knee leopard print dress. Chelmsford’s lace-up design allows ultimate adjustability with an inside zip so that, once the laces are set, you can use the inside zip for easy access. With a calf circumference of 36cm plus 10cm adjustability Chelmsford is perfect for people with wide or swollen calves.

Tasman and Chelmsford are the widest and deepest knee-high boots on the market, being available in our 2V(EE-4E) and 6V(6E-8E) variable width fittings, making them the perfect fit for even the widest feet.

We’re often asked whether our boots can accommodate wide ankles and calves and the answer is certainly a resounding yes! As specialists in wide and extra-wide footwear, we know that it’s not only wide toes that people have, but wide or swollen ankles and calves too. That’s why we offer boots with features such as calf circumferences up to 36cm and laces or buckles to offer the adjustability to fit perfectly to your ankle or calf.

Pair these with inside zips for easy access and you can set the fastening to your desired fit or style and simply use the zip for ease of foot entry.

So, even if you’ve struggled to find boots that fit in the past, we’re sure there’s a DB Wider Fit boot for you that will really fit, will be so comfy you won’t want to take them off and that will last!

And don’t forget that boots are versatile and can be worn with jeans, jeggings, skirts and even shorts!

You’ll soon find that the investment in one pair of long lasting, quality boots that offer comfort alongside versatile style will be worth multiple pairs of boots chosen purely for style that are so uncomfortable that they gather dust at the bottom of a wardrobe.

What’s more, with our free shipping on returns and exchanges, you can try our boots risk free and there really is nothing to lose (but so much to gain!)

If you’re in the UK and ordered the shoes directly from us and the shoes aren't quite right, for whatever reason, you can easily exchange them (unworn except for trying on indoors) for a different style, width or size. You can do this as many times as you need until you get the perfect fit, without paying a penny more in shipping, or take a full refund.

Not only do we offer free shipping on returns and exchanges, if your shoes aren’t right then you can also contact our customer services team on 01933 311 077 (Monday-Friday 9:00am-5:00pm) to discuss the problem with the shoes. This way we may well be able to advise a style with features more suitable for your loved one’s feet.

All our shoes are built differently to cater for different widths and issues so, if we know what isn't quite right with the pair that you have, we may be able to suggest one that will fit your foot better.

This means trying our shoes is risk free, even if you’re buying for someone else!

Browse all wide-fitting boots now >

Why not check out some of our other blog posts to help you with you feet.
Top 10 Boots For Winter »
Best shoes for being on your feet all day »
Your Wide Fit Autumn Wardbrobe »