Winter is coming, and we’re not referring to a certain popular TV show. That means the season of layering clothes and trying to keep warm without overheating or looking bulky. It’s a tough dilemma, but at Rydale, we’re all about finding that balance between keeping your body cosy whilst still looking stylish. And your footwear is an easy place to start.
A pair of chunky winter boots is a necessity during autumn/winter, whether you’re off to a casual event or a dressier occasion. Here are our top tips on what to wear with chunky boots this winter, from how to layer properly to wearing your chunky boots with dresses and skirts for a more feminine look.
Why Chunky Boots Are the Perfect Winter Staple
If you’re looking for your go-to shoe for the autumn and winter months, a pair of leather chunky boots should see you right through the next few months. They’re designed to be practical, but with so many new styles on the market, you can pick a pair that’s more casual like Chelseas, or dressier, such as heeled boots, to suit your lifestyle.
A pair of quality chunky boots should last you for years, as they tend to come in classic boot styles that are on trend year after year. However, they do require you to look after them by cleaning them regularly to maintain their look and their longevity. Especially if you purchase them in a classic, neutral shade, such as brown, tan or black, you’ll be able to dig them out every autumn season to keep your feet warm and dry.
How to Style Chunky Boots with Jeans
If there’s one item that’s as versatile as your chunky boots, it’s a pair of jeans. Dark wash jeans, especially, are the most wearable as they look flattering on all shapes and sizes, plus they’re always in fashion. A pair of well-fitting slim, skinny or straight-leg jeans give every woman a confidence boost, but we know it can take some time to find your perfect pair. Jeans shopping is all about trial and error. Our Ella jeans are made from stretchy denim material, making them much more comfortable than many brands.
Jeans and chunky boots will become your staple pieces as soon as the weather gets cold, so it’s all about what to wear on your top half. A cool day calls for cosy knitwear, and a cable-knit jumper with a crew or V-neck is the perfect fit. Add some colour to your outfit with a brightly-coloured jumper or opt for neutral or cool tones to keep your outfit muted. Throw on your favourite waterproof coat and you’re set for any countryside adventure, from simply walking the dogs to attending a local fair.
If you’re looking to dress up a little, a collared shirt is a great option to look smart but still feel comfortable. Your shirt should be fitted for smarter occasions, or if it feels too structured, a floaty, oversized blouse works just as well. It adds a feminine touch to any outfit, especially if you’re off for brunch with friends or to a family night out. Finish off the look with a tweed blazer to make the overall look feel even more dressy. You can even match the colours on your shirt to the coloured thread running through the tweed to make the outfit more cohesive.
Chunky Boots with Dresses and Skirts
If you think that you can only wear chunky boots with jeans, you’d be mistaken! Adding them to a more feminine outfit, such as dresses or skirts, makes your outfit look edgy. Sometimes, it’s just more practical to wear a pair of chunky boots, such as on the commute or attending outdoor country events.
A tweed skirt with chunky boots is a great way to look practical and stylish, especially if you pop on a heeled pair. Our Ella boots give a womanly touch for family events, like birthday nights out at the pub, and some much-needed height if you’re on the shorter side. The leather material is also waterproof, so they’re perfect for outdoor occasions too.
Whilst we wouldn’t recommend wearing chunky boots for the most formal occasions, they’re great for smart-casual events, including with a dress. We love pairing our rugby shirt-inspired Muston dress with a pair of neutral chunky boots. For the winter, stick on a pair of thick black tights and some cosy socks, and you’re set for lots of events over the next few months. A knitted cardigan and your favourite wool coat complete the look and make it a lovely outfit for casual lunch dates and Christmas shopping trips.
Layering Looks – Coats, Jumpers & Accessories That Work Best
As we said to begin with, layering in autumn and winter is key to not only keeping warm but looking stylish, too. It’s trying to find that balance between keeping warm but without looking bulky. Again, it’s a trick that you hone as you get older, but we recommend sticking to classic outer layers. Knitwear is an item that is on all the runways and high streets for autumn collections, with shades of browns and blues for 2025 seen across the board. However, our knitwear pieces are made to be timeless, from cable knits in every colour and style to ribbed V-neck and crew neck jumpers, perfect for layering over a collared shirt.
Your coat can make or break your outfit, but sometimes, it’s more important to dress for the weather. A tweed jacket will definitely keep you warm and cosy during the winter, especially if you’re layered up underneath. If you’re looking for a more casual jacket, a bomber jacket in your favourite bright or neutral colour adds a ‘cool girl’ touch to your outfit. They’re fully waterproof too, perfect for if you get caught in a sudden downpour when out and about. A wax jacket is just as practical, but several styles don’t have a hood attached, meaning you’ll need to carry your umbrella around, too.
If you’re looking for the ultimate outer layer, a changing robe will soon become your new best friend. The fleece lining is designed to keep you warm, and the waterproof outer layer will keep you dry, which is exactly what we’re all looking for in a winter coat!
When choosing what to wear with chunky boots, it’s all about cosiness and practicality over fashion. However, chunky boots are a timeless pair of shoes, making them a staple for years to come. Stick to a neutral pair, clean them regularly, and you’ve got a pair of boots that will see you through the seasons.
Wondering how to make every ensemble look more put-together? We've got plenty of style tips!
