Last updated on November 16th, 2023 at 12:39 pm
As trends and styles come and go, it can be tricky to know how to wear chunky boots with the right outfit. Luckily, chunky boots are one of the most versatile fashion pairings – and that isn’t looking to change anytime soon.
Whether they’re partnered with skirts, dresses, jeans, or smart trousers, a classic chunky boot goes with just about anything. A timeless staple for anyone’s wardrobe, it’s no wonder we’ve seen them loved by the likes of Olivia Rodrigo, Kourtney Kardashian and Miley Cyrus.
Not only do they look good, but they also have plenty of practical benefits too – which makes chunky boots even better. They’re comfy and durable, while offering plenty of support for everyday use.
Read on to explore how to style chunky boots with pretty much any outfit, from work to play.
What’s on this page:
- How to Wear Chunky Boots with Jeans
- How to Style Chunky Boots with Skirts and Dresses
- How to Wear Chunky Boots with Trousers
How to Wear Chunky Boots with Jeans
There are so many great ways to style chunky boots with jeans. Depending on how you twist this classic duo, they can transform a look from casual to chic in seconds. Style a laidback look with a classic biker jacket or dress them up with a flattering blazer for work or going out.
Here are a few of our favourite combos for wearing chunky boots with jeans:
- Skinny jeans – a classic pair of skinny jeans look great tucked into chunky boots. Dress them up with a nice top or keep it casual in a graphic tee.
- Wide leg jeans – wide leg jeans are back in fashion. Style them with your chunky boots peeking out for a retro 90s look.
- Mom jeans – the perfect balance between fitted and baggy jeans, a high-waisted mom jean has taken fashion by storm, redesigning the popular 80s style. They look great with chunky lace ups and Chelsea boots of almost any colour. Cuff your jeans for extra vintage vibes.
- Flared jeans –pair these statement jeans with smart, chunky heeled boots, or grab some combat boots to strike an early 2000s look.
- Cropped jeans – available in almost any style from bell bottom flares to skinny and straight leg jeans, cropped styles create a seamless flow between your jeans and boots. They’re a great transitional option for when the weather is cool, but not too cold for exposed ankles.
Lilley Women’s Tan Chelsea Boots with Buckle
These tan buckled Chelsea boots by Lilley have a rural design with an elasticated gusset and buckle for a snug fit. The chunky sole is supportive and practical, while the tan brown is timeless for both work and everyday wear.
Top Tip: Tan goes great with true blue jeans. Tuck these into a pair of skinnies or go for a cropped look by cuffing your jeans.
Vega70 Women’s Cream Lace Up Boot
Make a fashion statement in these cream lace up boots by Truffle. Neutral tones add a unique twist to this classic chunky style, while a thick heel and cleated sole make sure you’re both secure and stylish.
Top Tip: Taller than ankle boots, these lace up chunky white boots would pair great with some cropped flared jeans for extra impact.
Lilley Women’s Black Patent Zip Up Ankle Boot
Everyone can rock a pair of chunky black patent boots. These lace ups from Lilley have hidden zips, making them easy to throw on and head out the door. The synthetic material is also a great option if you don’t like wearing leather.
Top Tip: From skinny to mom jeans, a pair of chunky all-black stomper boots are as versatile as they come and match any colour in your wardrobe.
How to Style Chunky Boots with Skirts and Dresses
Chunky boots don’t just look great with jeans, they’re staples for skirts and dresses too. Easily elevate an outfit with a pair of trusty boots, whether you’re dressing up or down.
Create a smart, put-together look with chunky heeled ankle boots, or keep it casual with some retro combat boots. And the right jacket can complete any look. Try a denim or biker jacket for a lightweight extra layer, or grab a classy longline blazer coat for chillier days.
Whether it’s florals, patterns, block colours or neutrals, here’s how to style chunky boots with different lengths of skirts and dresses:
- Mini – from the humble mini-skirt to the LBD, chunky heeled and knee-high boots pair perfectly with this shorter length for transitional weather and going out.
- Midi – there’s something so effortlessly stylish about pairing a midi dress or split skirt with some chunky ankle boots, especially with florals or patterns. They’re great for work or even a cute brunch date.
- Maxi – chunky boots put an alternative spin on summer maxi dresses. In winter, match with a cosy jumper or cardigan.
Women’s Lace Up Ankle Boot in Black
A pair of chunky black ankle boots are a staple for any shoe rack. Zip up fastening and lace up front ensure secure fitting, while a thick heel keeps you steady and supported throughout the day.
Top Tip: Complete your skirt or dress with Ankle boots to transition your look from day to night. They also look super cute with tights.
Giovana2 Women’s Black Chunky Boot
If you’re looking for chunky boots, you’ve found the holy grail. These black chunky boots by Truffle are platformed for extra height. But don’t worry about getting them on and off – the slip-on function couldn’t be easier.
Top Tip: Pair these boots with mini skirts or dresses for a contrast in thickness and length – and make them extra chunky for a grungy twist.
How to Wear Chunky Boots with Trousers
A good pair of trousers can bring an outfit together and mix up your wardrobe from the usual dresses and jeans. They’re pretty versatile and almost always look put-together – whether it’s part of a co-ordinated set, a smart pantsuit or some patterned tailored trousers worn with a simple top. The perfect pair of chunky boots can really seal the deal.
- Straight leg – the quintessential straight leg trouser goes well with traditional laced boots and chunky soles.
- Peg trousers – a pair of cropped peg trousers offer a tailored look, whether they’re plain, bold or have a stylish checked design. Partner with chunky heeled boots for work, or keep it relaxed with a slouchy tee and Chelsea boots.
- Wide leg – match chunky zipped boots with the flared style of wide leg trousers or culottes to deliver an instantly chic silhouette, excellent for going shopping or heading somewhere smart.
Truffle Edison2 Women’s Black Zip Up Boot
If you’re aiming for a statement look, you can’t go wrong with the Edison2 Women’s black boots from Truffle. The sturdy platform heel provides extra height, with a unique stretch sock upper for a comfy fit.
Top Tip: Imagine these peeking out of a pair of tailored trousers, perfect for going out. Or how about a pair of flared trousers for a 70s vibe.
Women’s White Lace Up Boot
This pair of white chunky platform boots by Sedai promise ultimate comfort and style. Just pull them on with a pair of plain or patterned trousers and you’re ready to take on the day.
Top Tip: Try these lace up boots with cropped trousers for an effortlessly sophisticated look.
Heavenly Feet Justina Women’s Black Lace Up Boot
Heavenly Feet’s rugged take on black ankle boots is the perfect addition to your everyday footwear. Despite their all-black design, the Justina boots are anything but plain with fine stitch details, a red-striped shoe tab and sturdy gripped soles.
Top Tip: Whether you pair these boots with bold animal print or neutral checked trousers, they’re sure to make a statement. You could even try a new shoelace style to elevate your look.