10 Outfit Ideas to Style Chelsea Boots Womens

what to wear with chelsea boots

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Well, who can deny that Chelsea boots add a little extra spark to any given attire, don’t you agree? Another great find is these ankle booties I’ve been using for years, they’re stylish and punk at the same time and very comfy. Chelsea boots, therefore, have relatively fewer heels, stretch side, and general appeal yet they are so fashionable.

However, as anyone who has actually tried to build outfits with them knows, it can sometimes be a little difficult. Do you want the laid-back sophistication of the boots to come through and what other looks complement these boots?

Well, my fashionable friends, I’m revealing 10 Outfit Ideas to Style Chelsea Boots Womens and how I have been rocking my Chelsea boots for women this season.

1. Skinny Jeans

We are kicking things off with an absolute classic combo – Chelsea boots with skinny jeans. This duo is pretty much a no-brainer for me, and good reason.

chelsea boots outfit

The sleek lines of skinny jeans complement the streamlined look of Chelsea boots so well. Plus, that cropped bootie length creates an awesome lengthening effect on your legs. Such a flattering look!

My top tip here? Look for skinny jeans with just a bit of stretch so you can tuck them into the boots easily. Then style it up with an oversized chunky knit sweater or a fitted turtleneck on top. So cozy yet pulled together! Throw on a crossbody bag and maybe a cool moto jacket if it’s chilly out.

2. Leggings

Especially when I do not want to wear anything fancy and just want to feel super comfy but at the same time I still want to look somewhat fancy, Chelsea boots go hand in hand with leggings. No kidding, this pairing screams comfort and warmth and is still roared in fashion.

For leggings, I prefer thicker, opaque, and concealing leggings type in any neutral shade preferably black or olive green to get that athletic leisure kind of vibe.

chelsea boots style

But you know what? While there is always a time and place for solid-color clothes, don’t be Hesitate to incorporate some prints into your wardrobe as well!

I remember leggings in bright or daring prints, such as camo, or snakeskin, and pairing this garment with Chelsea boots is just so awesome. Many a time, you can put on an oversized sweater or a sweatshirt dress on top and you are good to go, with an added touch of attitude. Put on a jean jacket or utility jacket in case you want to get an extra cover.

3. Shorts

Who says Chelsea boots are just for cold weather? These booties were seriously made for a short season! Pairing them with casual bottoms like boyfriend shorts or denim cutoffs creates such an effortlessly cool summer uniform.  

chelsea boots fashion

For a little trendier vibe, I personally love contrasting the ruggedness of the boots with feminine details up top. A flowy camisole with lace trim or a flutter sleeve top balances everything out so nicely.

Oh, and don’t forget to accessorize with a crossbody bag! You can even knot a jean jacket around your waist on breezy days.

4. Dress

Alright, I know this one may sound a little counterintuitive but let me explain it – Chelsea boots are those that make any dress look effortless! Whether it’s a simple shirt dress or a cute mini dress, these booties just add the edge you need to your look.

styling chelsea boots

However, to get the best out of this combination, you should ensure that the dresses do not touch the knees or go below. Anything much longer can start to look a bit awkward with the shorter bootie profile.

However, don’t hesitate to experiment with different fabrics and lovely details! An example of such an outfit is a floral print dress worn with Chelsea boots.

How to Wear Chelsea Boots with a Maxi Dress?

Even for the most experienced fashion chic it is a rule not to wear ankle boots with maxi dresses I have found a solution here. The secret? For this outfit, check for a thigh-high slit in a maxi dress so that you can show the Chelsea boots.

It perfects the dose of romance adding the touch of danger to compensate for the aura of the delicate and tender woman.

Chelsea Boots with a Maxi Dress

If you are wearing a dress, this look can be pulled off, especially if the dress has sheer paneling or cutouts on the bottom to show a little bit of the booties. The proportions should be correct though, so if you’re wearing the dress you should ensure that it comes just up to your ankles or you show a bit of leg.

Do not add many accessories or any other form of glamour to that attire because this boots and dress combination is going to headline the movie!

5. Skirt

Another unexpected but so chic way I’ve been wearing my Chelsea boots? With skirts! This footwear choice gives such a cool, tough-girl contrast to skirts of all varieties.

chelsea boots style
image – Pinterest

What Types of Skirts Pair Well with Chelsea Boots?

Some of my personal favorites for this look include:

  • Denim skirts (either mini or midi length)
  • Sleek pencil skirts  
  • Pleated midi skirts
  • Faux leather skirts
  • Suede mini skirts

Just use your best judgment on the skirt length. Anything too short or too long can throw off those proportions and look a little off with the shorter ankle booties.

How to Wear Chelsea Boots with a Midi Skirt?

All right this trend has been going ape lately and I can now completely understand why. A midi skirt and it does not matter if it is skinny or fuller, just looks so classy when paired with Chelsea boots. It is an even better combination, the high-end and the low-end.

For instance, you can decide to wear a ribbed knit midi skirt together with a tight turtleneck tucked in. Or opt for a playful pleated midi skirt with a sporty graphic tee and an oversized blazer on top. The key is to tone down that longer skirt length on the bottom by pairing it with slimmer and more fitted clothing on top.

You don’t even have to restrict each outfit to one type of fabric or print – have fun with it!

6. Blazer

I mean, there is nothing more that is ‘dressed down’ chic than pairing Chelsea boots with an oversized blazer right? It is precisely the contrast of a well-tailored exterior with slightly more relaxed footwear underneath that makes this clothing pairing look best.

For this look to be perfect, you should look at getting an elongated slightly oversized blazer that should touch your thighs or even slightly past the thighs.

chelsea boot outfits

Next, slip on a tight-fitting turtleneck, tank, or bodysuit over your clothes or under your dress. Skinny jeans or leather leggings would work well too if you want to achieve that polished look.

If you really want to take the borrowed-from-the-boys look to the next level, wear the blazer belted at the waist, over a pair of jeans, and top it off with a newsboy cap. Complete all of these outfits with a structured tote or briefcase for that ultimate boss vibe!

7. Leather Jacket

As for the trusty leather jacket and Chelsea boot look, nothing quite says punk meets pin-up beauty quite like it. Boy, oh boy, these two pieces could have been created for each other!

As for the underneath attire, I prefer to retain a simplistic approach and opt for a fit T-shirt or crop. Sometimes I slip on a timeless leather motorbike or JFK-style leather trench coat. It’s important to search for one that will cover the skin to a length that can reach a little bit above the knees or right at the center of the thighs where the shorter booties reach.

chelsea boot outfits

From there, one can choose the outfit he or she desires to wear or whatever garment one wants to wear depending on the occasion. It can be relegated into a tight, high-waisted skinny pair of jeans for the lean, nonchalant, wake-me-up-in-the-morning model-off-duty appearance.

Or if you want to stick more to the classic business casual but with that rebellious touch, you can always opt for leather leggings or coated skinny jeans. All you then need is a cross-body bag and perhaps a slouchy beanie if it is cold back.

8. Suit

Who says suits have to be worn with pumps or loafers? I’m personally a big fan of rocking Chelsea boots with suits for an instantly cooler, more modern feel. It lets you put such a fresh, trend-forward spin on this classic workwear staple.

Black or navy suit pants or trousers look amazing with a pair of slim, streamlined Chelsea boots. Then you can play around with different blazer styles on top, from more tailored and fitted to long and slouchy. Such a vibe!

Or, you can switch things up by swapping out the pants for a mini skirt or dress from the same suit set. Just make sure the hem hits at or above the knee to balance those proportions. A sleek fitted turtleneck layered under the blazer pulls everything together flawlessly.

9. Jumpsuit

This is a very easy outfit for anyone who wants to put in zero effort and just leave the house – a jumpsuit and Chelsea boots. This pairing just screams a chic Parisian look with little effort needed in the outfit department.

Opt for the jumpsuits with flowing, trapping materials with a cinched leg/ankle area to fit your footwear. I like those functional, mechanic-type jumpsuits a lot right now – they really fit well with that kind of boots.

However, you can also take it up a notch by wearing something more glamorous such as a sexy or fancy jumpsuit, whether it is made of silk or satin.

You can attempt to gather the material around your waist and pin it in a way that makes you look less like you are falling out of your dress. Then complete it with a tailored structured blazer or a light trench – perfect!

10. Culottes

Alright, if you haven’t tried the culotte and bootie combination yet, then you are missing a lot of life’s beautiful experiences! These cropped, wide-leg pants are a great opportunity to wear a fashionable pair of Chelsea boots.

What I like about the outfit is how the streamlined bootie peeks out from under the cropped, slim tapered culottes. It forms an interesting counterpoint and makes the figure balanced in terms of proportion.

I would avoid going all cubical by adding fitted knitwear above my culottes, whether it is a slim turtleneck or bodysuit.

It’s possible to go for a monochromatic outfit wearing a dress that is in a primary colour such as black or camel.

Or just play with patterns and wear a culotte with a print while pairing it with a plain piece of clothing. However you bend it, this sort of combination seems so trendy!

Can Chelsea Boots Be Worn in Different Seasons?

Last but not least, one thing that I particularly enjoy about Chelsea boots is the fact that they can be worn in any season. During the fall and winter, they complement well when I am wearing chunky knits, oversized coats, and other warm layers.

The low block heel makes them extremely comfortable to wear for slogging through snow or rain.

However, when summer sets in, Chelsea boots are a revelation! They’re a staple in my wardrobe for dressing up flowy dresses or Sporty outfits comprising of denim shorts and what have you! Perhaps it is because the smooth leather emanates such a cool girl’s aura. Just be sure to try an unlined, lightweight shoe to prevent the feet from getting too hot in them.

What to Wear with Chelsea Boots to the Office?

Chelsea boots are seriously a godsend when it comes to looking polished and professional for the office. Their sleek, streamlined shape instantly pulls together any work-appropriate outfit.

One of my go-to looks is tucking a pair of slim ankle trousers into my Chelsea boots, then throwing on a crisp button-down or silk blouse on top. Add a fitted blazer and you’ve got such a chic, pulled-together vibe going on.

You can also get away with wearing them with a sheath dress or tailored midi skirt. Just make sure the hemline hits at or around the knee to balance those proportions. A sleek turtleneck layered under shifts the look into more business territory.

The important thing is to limit the fuller and more formal outfits at the top and bottoms to hit right at the boot ankle opening. Formal blazers, trench coats, and structured handbags are fitting accessories.

What to Wear with Chelsea Boots to a Party?

Don’t think for a second that Chelsea boots can’t work for dressier occasions too! With the right styling, they can absolutely carry you through any holiday party or night out in style.

For a cool girl look, I love pairing my Chelsea boots with a slinky slip dress or silky camisole. Something with a cowl neck or lace detailing gives it that perfectly undone yet elevated feel. Throw an oversized blazer or a cropped fuzzy jacket over top when you need another layer.

You can also edge up any LBD by swapping out the expected pumps for some Chelsea booties instead. Add a leather moto jacket for an extra touch of attitude. So chic!

Can Chelsea Boots Be Worn for Formal Occasions?

Chelsea boots can be quite casual although you can formally wear them for formal occasions if properly channeled. This is exactly why it is critical to avoid messy and shabby chic on the table and choose jewel-like objects and crème de la crème of fabrics.

For instance, I have gone with Chelsea boots, ankle-length tuxedo pants as well as a silky camisole. Simply adding a very tailored modern longer blazer or over wool coat instantly adds formality to the entire look. To replicate this look, stick only to pieces in black and navy blue to get that elegant look.

You also don’t have to stick to casual wear on your top half when rocking Chelsea boots and there’s room for dressing it up a bit – like opting for gorgeous midi velvet or satin dress.

Make sure the dress comes exactly to the knee and keep any booties clean with as little straps and ruffles as possible. A smart woolen coat or a trench would blend well to complement and complete the look.


And there you have it, folks – 10 new and easily adaptable trends for wearing your Chelsea boots this year! As we have observed, these stylish ankle booties are not only fashionable during the colder months of the year but much more.

With those clothes and accessories, they can safely take you through pretty much all the styles and events throughout the year.

The actual challenge lies in this balance between the boots’ relaxed, city vibe and these other sharper, dressier pieces. Do not hesitate to ‘play it up’ by incorporating quirky elements such as midi skirts, blazers, or silky dresses. And it is that high-low contrast that makes Chelsea boot outfits so chic.

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