Chelsea – the most fashionable shoes of autumn 2020

We’ll tell you which Chelsea are trending this season and choose the perfect pair of boots for a cold fall.

Chelsea is jokingly called boots for the lazy – they have no laces, they are easy to put on and take off and this fall they will become indispensable in your wardrobe. Classic Chelsea usually end at the ankle and feature side panels. Over the years, black chelsea were popular – they were worn with classic suits, and they gave the business look a completeness, however, with the development of street style Chelsea began to be worn along with jeans, tops and even dresses.

History of creation

The first Chelsea boots were originally created for Queen Victoria – it was she who asked to come up with shoes for horse riding without many laces. Of course, in the original version, the Chelsea looked different – the cape was sharper and different in color. However, one detail that has remained unchanged in the modern world is elastic side inserts, however, in the fall of 2020, designers prefer to make them more contrasting. It was rumored that Queen Victoria wore Chelsea every day: this fact was the best advertisement for comfortable shoes.

Chelsea officially got their name in the 1950s: these suddenly popular boots were worn by musicians, artists and socialites, and in the 1960s, at the request of Paul McCartney and John Lennon, the Cuban heel was added to the design of classic Chelsea.

Chelsea with heels or massive platform

Photo: Giambattista Valli Fall-Winter 2020–2021

A few years ago, the top featured chelsea with low heels and flat soles – a good find for those who are constantly in a hurry. However, this season, designers have reinterpreted the old trend and added a high, stable heel and a chunky platform to the Chelsea. Such a shoe detail will reduce the degree of a business look and make it more free and relaxed. Fendi’s silver chelsea heels are the perfect substitute for your favorite shoes in chilly weather.


1 – Stella McCartney, 2 – Ekonika, 3 – Fendi, 4 – Jil Sander, 5 – Ganni

Jil Sander and Stella McCartney did not stop there and decided that the contrasting chunky sole would be the best accent in any look – and they were right. Wear these chelsea together with a cape coat, leather dress or latex jumpsuit – not only stylish, but also practical (now no puddle is scary for you) will complete almost any look.

Chelsea with contrast panels

Photo: Stella McCartney Fall-Winter 2020-2021

As for the chelsea color scheme, designers still prefer basic shades: gray, black, red, brown and maroon. It is easy to combine them with a basic autumn wardrobe, and if you suddenly wanted variety or bright accents, then feel free to choose Chelsea with contrasting inserts – another trend of this fall.


1 – Alexander McQueen, 2 – Sxarosso, 3 – Thom Browne, 4 – Bottega Veneta, 5 – Burberry


These shoes will undoubtedly become the main accent in any monochrome look – wear Burberry Chelsea with a classic beige trench coat and light beige trousers. However, if the weather outside the window does not leave room for walking in light clothes, feel free to put on a chelsea with an accent belt and wear them with your favorite jeans or a pleated skirt.

Chelsea with decor

Photo: Giambattista Valli Fall-Winter 2020–2021

This season, brutal Chelsea, which at one time were all worn under leather jackets, biker jackets, were replaced by more glamorous and feminine models. The decor can be varied, from studded straps to beads that adorn the sole. These Chelsea shoes will certainly be a good alternative to beautiful evening shoes: wear them with a little black dress, a skirt made of flying fabric or snow-white jeans.

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1 – Valentino Garavani, 2 – Stuart Weitzman, 3 – Off-White, 4 – Pierre Hardy, 5 – Ecco

The designers of Giambattista Valli suggest wearing such chelsea along with a coat decorated with feathers – another fall 2020 trend, or with a formal suit with a skirt. And Chelsea in suede will come in handy in dry weather – these discreet models will complement any look and make walking around the city more convenient and interesting.

What to wear with chelsea

Modern Chelsea shoes are the perfect match for both jeans and dresses, so this type of shoe is suitable for both casual and formal looks. We recommend wearing bright chelsea with an animal print along with a monochrome look: leather tight-fitting trousers, a classic oversized jacket and a tote bag.




Jeans are a staple of any wardrobe: this season, look at light-colored straight-leg jeans for the perfect fit for this fall. This outfit with a bold blouse, a gray coat and beige chelsea isn’t so hard to score and is open to more sartorial experimentation.

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The shirt dress has stayed with us since the summer of 2020, but instead of colorful models, designers suggest focusing on more classic models this season. A beige shirt dress made of dense fabric will be the perfect companion this fall, and stylists suggest choosing spectacular black chelsea with a metallic cape to match the classic outfit. Dark sunglasses with a black rectangular bag will perfectly complete the laconic autumn look.




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