Chelsea boots can look effortlessly stylish. They have that kind of haven’t-tried-to-hard, slightly androgynous look which can look fabulous, particularly for fall.

In this article we will give you lots of inspiration on how to wear Chelsea boots.

How to wear Chelsea boots

Chelsea boots can be a tricky look to pull off. This boot length has the potential to make your legs look larger than they are by drawing a horizontal line right above the ankle.

But there are plenty of outfit ideas which can make Chelsea boots a flattering option.

Not only that, but they can also be one of the most comfortable types of footwear for you, as many Chelsea boots are flat, so you don’t have to worry about walking in heels if you don’t want to.

What are Chelsea boots?

First of all, what classifies Chelsea boots as Chelsea boots rather than any other ankle booties?

They are generally defined as boots which are slim-fitting, ankle height, and which have an elasticated panel at the sides. Although, this season, I’ve seen lots of Chelsa boots where instead of the elastic panel, the side has been left open to create a cut-out effect.

Chelsea boots can trace their origins back to Victorian times, so they’re definitely a style staple you will have in your closet for years to come. As such, they are one of the classic pieces that you can afford to invest a little more in as you know they won’t go out of fashion next season.

You can wear your Chelsea boots with pretty much everything. Any jean style will go with them, but if you are wearing bootcut or boyfriend jeans, don’t try to tuck them. Instead, wear your jeans over your boots for bootcut, or create a cuff above them for boyfriend. Here are some more outfit ideas for you.

Chelsea boots outfits

Here are some of the most flattering Chelsea boots outfits you could try this fall, as well as tips and tricks to wear them so that they elongate your legs rather than visually cutting them off at the ankle.

1. Tuck your chelsea boots

Most of us, unless we’re lucky enough to have long legs already want to create longer, leaner lines. Tucking your Chelsea boots into your pants can create a long leg line. It’s best to look out for jeans which are fitted so they fit neatly into your boots.

Looking for jeans and boots which are similar colors such as these black ones below will also help to lengthen your legs if you are petite.

Classic outfits you'll love with chelsea boots |

Good American jeans – Marc Fisher LTD – Halogen lace jacket – Halogen tunic

Or you could try a pair of leggings instead. Check out these tips for more inspiration on what to wear with your leggings.

If you want to create a tucked look, make sure your jeans or leggings are long enough so they fit into your booties.

2. Wear your chelsea boots with a rolled hem

This is a look which is very on trend. But, it can be difficult to wear if you are petite or you have shorter legs because the cuff does have the visual look of cutting off your leg at the ankles.

If you have longer legs though, this can be a great look. One way to create a nice look is to leave a little bit of ankle showing as your ankle is likely to be one of the slimmest points on your body.

Tips on how to style cuffed denim with chelsea boots |

Sarto chelsea bootKUT from Kloth jeansTreasure and Bond sweaterHalogen pearl drop earrings

Choosing a pair of Chelsea boots which have a cut-out either at the front or at the sides will help to show off a little ankle.

3. Chelsea boots worn with a dress

How to wear chelsea boots with a dress |

M&S long sleeve dressBella Vita chelsea bootNordstrom crossbody bagM&S shell layered necklace

Wearing Chelsea boots with a dress is an ideal way to continue wearing your summer dresses during fall, or to transition from winter to spring when you no longer need longer boots. Just add some opaque tights if you need extra warmth.

4. With a pencil skirt

Outfit ideas on how to wear chelsea boots with a skirt |

Everleigh knit pencil skirtHalogen sweaterRebecca Minkoff watchSole Society toteSarto chelsea boot

You can definitely wear Chelsea boots with a more fitted skirt. I would keep the look tonal, so if you’re wearing with tights, stick to boots in the same shades.

Or, if you have bare legs, I find boots with a lighter hue work best. Dark shades can look heavy and draw the eye downwards.

5. A touch of animal print

Animal print chelsea boot outfit |

Ralph Lauren coatBlondo bootiesFrame boyfriend jeansBoden sweaterBody white blouse – Boden geometric pendant

If you want to introduce some animal print into your closet, but don’t want to go too full-on, wearing it on your Chelsa boots is a very stylish option.

Leopard print is a print which is always been on trend. Can you remember a year when leopard print wasn’t stylish? But, snake print is particularly on-trend for this fall. Either will look great.

Do you already have Chelsea boots in your closet? Have you been inspired by these how to wear Chelsea boots ideas?


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How to wear chelsea boots: 5 perfect outfit ideas |


Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. An alumni of the School of Color and Design, she is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.

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