rockingham collection

Boot Pairing Perfection: Matching Your Ankle Boots with Different Bottoms

by Charlie Cooke,

First Published: 13 Mar, 2024

No matter your personal style, everyone should have a pair or two of reliable ankle boots in their footwear collection. Not only does this style of shoe never go out of fashion, they are versatile enough to be worn all year round and for so many different occasions. Ankle boots are the all-round hero footwear item!

If you’re feeling like you’re stuck in a fashion rut right now with how to style women’s ankle boots during the transitional months from winter to spring, then we’re here to offer our contemporary style advice the traditional Fairfax & Favor way.

To heel or not to heel

Heeled ankle boots are a fabulous option for elongating the legs effortlessly and when you want to dress up a more casual outfit. They are also an excellent, edgy alternative to other types of heeled footwear that will suit those looking for an instant modern update.

Flat ankle boots are highly functional and comfortable whilst also providing that much coveted cool style. Master how to wear ankle boots with any type of bottoms, from skirts, jeans and even dresses and you’ll truly expand your wardrobe horizons with minimal effort and maximum finesse.

All dressed up

Firstly, don’t be afraid to pair your ankle boots with a dress – they can be just the finishing touch you need! From floaty maxi and mini dresses in the summer to midi length dresses in the autumn and winter months, a slick pair of boots can set off a feminine outfit wonderfully by adding an unexpected edge.

Team a pair of tan coloured suede ankle boots, such as The Chiswick, with a patterned maxi dress and tailored jacket for impeccable seasonal styling suitable for countryside weddings in the summer or last minute date nights. Going with tan or cream coloured ankle boots over darker shades during the warmer months will work well with the naturally lighter colour palette of your wardrobe. 

For when there’s still a chill in the air, another outfit option is a ribbed knitted mid-length jumper dress cinched in at the waist with a belt and luxe leather ankle boots. The Boudica boots in black waxed leather is a sensational design that would coordinate nicely with a jumper dress. Throw on a chic trench coat if needed, and enjoy the added snuggly shearling lining of the boots that will certainly keep your toes warm during those colder evenings enjoying drinks around a fire pit or Sunday afternoon walks.

Skirt and boots = perfect match

A tartan or herringbone pattern mini skirt worn with a blouse and tights is a transeasonal outfit that is just crying out for a pair of black suede ankle boots. With this look you can choose from heeled boots or flat ankle boots to suit the occasion, but we love a sassy heeled ankle boot for a relaxed dinner date outfit. The Belgravia is a flawless example of the type of heeled ankle boot that promises timeless style with its iconic design and its sultry block heel provides extra height to help you rise to the occasion.

If you’re looking for a way to incorporate your new favourite ankle boots with your everyday workwear, the good news is that this shoe design can also work surprisingly well with formal ensembles. Office-ready pencil skirts are a sophisticated skirt style to pair with heeled ankle boots, such as The Regina Ankle suede boots. The lift of a heeled boot is the perfect accompaniment here and will stop the longer skirt length from looking frumpy. Remaining smart and refined, embracing ankle boots in the office could be the modern twist to your work wardrobe that you’ve been searching for!

Cool and casual: jeans and ankle boots

For a quintessential countryside aesthetic, flat ankle boots in the popular Chelsea boot design is an absolute must-have for a cool and casual weekend ensemble. Worn with skinny jeans, a crisp cotton shirt and a quilted gilet, you can so easily fit the brief for relaxed yet refined attire perfect for pub lunches in the Cotswolds or doing a spot of shopping with friends. We love the Brogued Chelsea boots in rich mahogany leather as an unrivalled option which will work beautifully well with indigo blue skinny jeans tucked in or cuffed jeans that sit nicely on the edge of the boot.

Alternatively, you can rely on your designer heeled ankle boots to elevate an even more relaxed outfit of black jeans and a t-shirt. Tap into the Western trend with our Rockingham heeled ankle boots in ink suede and contrasting wooden block heels for something a little different when the dress code calls for informal and easy-going attire.  

From sophisticated heeled boots to definitive flat ankle boot designs, we’ve got an exceptional collection of Fairfax & Favor women’s boots that exude pure style for you to explore and find your next pair of favourite footwear.

Ankle Boots

The Oakham - Women's Ankle Boot - Black Suede The Oakham - Women's Ankle Boot - Black Suede