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The dos and dont’s of wearing your winter boots

November 10, 2017

I shouldn’t use the word rules, especially when it comes to fashion where rules are made to be broken. But I do have a lot of clients who like me to give them ‘rules’ as this simplifies the outfit building process and takes the stressful decision making process out of their day. So I thought it would be helpful to share with you my do’s and don’t when it comes to styling your boots because the wrong shoes can completely destroy the effort you put into choosing an outfit. 


Ankle boots… 

DO wear them with mini skirts and dresses, maxi skirts and dresses, cropped and flared jeans or under tailored trousers. 

DON’T wear with with midi skirts if you have shorter legs as your legs will look even shorter. And don’t wear them with full length skinny jeans as the jean will bunch around the ankle and shorten your legs and widen your calves. 

Knee high boots

DO wear them with midi skirts and dresses, knee length skirts and dresses, under wide trousers or cropped culottes

DON’t wear them with mini skirts if you are tall (fine if you are petite). The jury is out whether it is acceptable in 2017 to wear boots over your jeans…. I would say proceed with caution. Though I did see Pernille Teisbaek wear incredible zip Celine boots over jeans with aplomb so rules are made…

Over the knee boots

DO wear over your skinny jeans, with tights and aline mini skirts and dresses, under knee length dresses and skirts or maxi dresses and skirts and you negate the need for tights. 

DON’T wear with very tight fitted dresses or skirts as you are too easily veering into Pretty Woman territory. 


Lace-up leather ankle boots – Refined enough to wear well with both tailored and casual trousers. 

Desert Boots – I love Red Wings for a cool casual look with denim. 

Chukka boots (Possibly named after ‘chukka’ a period of play in polo)  – The suede versions or those with a crepe rubber soles are great with casual trousers and jeans. Leather versions work well with tailored trousers or casual trousers. 

Chelsea boots (though the elasticated design was patented in 1851, the name ‘Chelsea’ was attached to the boot due to its popularisation in the 60s with groups such as The Beatles and their association with King’s Road in Chelsea) – There are many iterations of this versatile boot with its laid back elegance. A suede pair will work well with jeans and casual trousers and a leather pair with tailoring or jeans. 

I hope this will takes some of the guess work out of your shoe choice but if you need more personalised advice, please get in touch

Penny Bennett is a Personal Stylist and Personal Shopper and Image Consultant who works with successful men and women from London and the south east who love to look confident but lack the time and inclination to shop for themselves.

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