Style guide: winter boots © Tom Ford

When it comes to the art of boot wearing this season, it all lies in the heel and the height...

Heels, flats or something in between? Ankle high, knee or thigh grazing? Bare legs, tights or ankle socks? These are just a few of the footwear dilemmas I go through on a daily basis once winter sets in.

Summer's flesh baring ballet flats, open toed heels and calf entwining gladiator sandals are all banished to the back of the wardrobe and replaced with hard wearing, feet encompassing shoes and boots. And while there are some seriously lust worthy shoes on the style agenda this winter, right now, I am all about new season boots.

So what does this winter have in store? What are the rules to obey and the myths to break? Should we be thinking style over practicality and putting a very fashionable foot forward whatever the consequences?

Boots are fundamental to winter dressing each and every season and with the right pair of boots, you can't really put a foot wrong. And this season it's all about the heel and the height. There are really only three heels in the running - chunky, block and flat, and three heights to consider – ankle, knee and thigh...


If you are opting for an ankle boot you can pretty much go for any style, from flat buckled bikers to sleek Chelsea boots or square heeled leopard print to sleek day to night black patent.

Use your ankle boots to pep up simple staples and off-duty basics or add edgy glamour after dark, and don't be afraid of colour and embellishment for added impact. And while the stiletto isn't top of the heel hit list this season, when it comes to ankle boots and evening wear, a towering black stiletto heel, adds killer elegance.

You really can make a statement in ankle boots. Chloe's quilted panel leather lovelies and Isabel Marant's leather and fur pair, are both great examples. Wear your ankle grazers with skinny jeans and cropped trousers or mini or midi skirts with bare legs, until the temperatures truly plummet.


Knee high boots are a must this winter and if you only have one pair in your wardrobe this season, make them flat and black, leather or suede and either riding boot or horse-bit. They are so versatile and easy to wear; you won't want to wear anything else.

Team them with a simple 60s shift or A-line skirt for an instant look changer and modish retro feel, or wear over leather leggings and a shirt or chunky knits for a louche finish. Look for buckles, studs and zip detailing to update classic black leather and add a chunky block heel for a slice of new season glamour. For a softer approach, grey and tan slouchy suede boots are the perfect antidote to lazy weekend style.


If you are feeling a little more daring, a pair of over the knee boots, are the way to go this winter and if worn correctly are the epitome of chic. To avoid the Pretty Woman association, there are a few key rules to follow...

Choose your fabric carefully – black leather is a classic option, or for something more laidback, go for soft grey or tan suede. They needn't be skin-tight either, choose supple slouchy leather or elastic backs to help slip on and off. Wear over skinny jeans, leggings and leather pants for a chic finish and if you are going to wear them with a mini skirt, wear with tights for a more conservative appeal. Ditch the stiletto this season and opt for a low block or flat heel.