What to Wear With Chelsea Rain Boots: 8 Cute Outfit Ideas for Short Rain Boots

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What to Wear With Chelsea Rain Boots- Cute Outfit Ideas

If the rainy days have hit your area like here, you may be on the lookout for some cute Chelsea-style (short) rain boots. Or maybe you already found some and just need some help figuring out what to wear with Chelsea rain boots. I’ve got you covered!

Chelsea Rain Boots can be your go-to for a rainy day outfit. Some of the best budget Chelsea rain boots I’ve found are from the brands Asgard and Planone; but you can also level up with brands like Joules and Hunter. They are very versatile in outfits: Wear short rain boots with skinny jeans, sweater dresses, skirts, black leggings, wide-leg pants and more. Read on for details on where I got my budget-friendly boots and outfit inspiration for the rainy days ahead!

What is a Women’s “Chelsea” Boot?

Chelsea boots are basically an ankle boot with an elastic side panel. That side panel makes them SO comfortable!

They are actually a common style for both men and women.

Why are they called “Chelsea” boots? Apparently their design originated in British city named Chelsea. The style was first created in the Victorian era but became popular again in the UK in the 1950’s and 60’s.

Now they are back in popularity–something I’m glad about because they are easier to wear and style than tall boots!

In this blog post, I’m focusing on the “rain boot” style, which just means they’re made of waterproof material versus leather or suede.

Budget-friendly Chelsea Rain Boots from Amazon - and what to wear with them

Chelsea Rain Boot Options for Women 

Popular Brands for Chelsea Rain Boots on Amazon

These are some well-known brands, but also a bit pricier.


I didn’t personally buy a pair of these because it’s the popular brand. I was purposefully on the lookout for an alternative! But considering how popular this brand is, you probably will love a pair of Hunter Chelsea boots!

Hunter Footwear Women's Ori...Shop on Amazon


These were a comfy, cute pair. They come in several neutrals and sheens, as well as in cute prints! A shiny pair will tend to feel dressier than a matte finish–it depends if you’re looking for casual wear or planning to wear them to work.

Closeup of black Joules brand short Chelsea rain boots
Joules Women's Rain Boot, B...Shop on Amazon Joules Women's Rain Boot, D...Shop on Amazon


This pair was SO cute–the color!–I almost kept them. But since they didn’t quite go above my ankles, I knew my socks would show and they wouldn’t look cute with tall socks folded over my jeans… so I returned them.

Closeup of yellow Bogs brand short Chelsea rain boots
BOGS Women's Kicker Rain Ch...Shop on Amazon

Budget-friendly Chelsea Rain Boots on Amazon

These brands are less well-known but still offer great quality at lower prices.

Most of these come in lots of colors and/or prints! I recommend starting with a neutral black, navy, or gray one for your first pair.


I live in the rainy Pacific Northwest so my first pair of black rain boots were from this Asgard brand on Amazon and they became my go-to pairs of shoes in the fall, winter, and spring. I literally wear them more than any other pair of shoes I own during the rainy season!

I used them for two years, almost daily and they never leaked or cracked–the only reason I replaced them was from scuffing after so much use!

Asgard Women's Ankle Rain B...Shop on Amazon Asgard Women's Ankle Rain B...Shop on Amazon


These were very light, like Crocs. A great option but not quite as good customer reviews as the similar Asgard brand I talk about above.

Closeup of olive Totes brand short Chelsea rain boots
totes Women's Everywear Che...Shop on Amazon totes Women's Everywear Che...Shop on Amazon


If you’re looking for a super warm version of Chelsea rain boots you’ll probably love these with a plush lining inside like sherpa. I personally would overheat in this but for those living in freezing temperatures, they may be perfect!

Chooka womens Waterproof Pl...Shop on Amazon


I kept this pair! ✅ (see my outfits below)

This was one of the only brands that carried this Rose pink color that I knew I wanted for my next pair of short rain boots. They have more chunky soles (another trending style) and so far have fared well. They do show some scuffing after just a few wears on gravel for recess duty.

Closeup of Rose Pink Planone brand short Chelsea rain boots
planone Short rain boots fo...Shop on Amazon planone Short rain boots fo...Shop on Amazon

London Fog

I kept this pair! ✅ (see my outfits below)

How appropriate… a brand named after the region where the Chelsea style originated!

I loved the leopard print on these and the slimmer profile.

I’ve been wearing them on repeat when my outfit is solid (versus print) or when the print goes well with leopard, such as stripes!

Closeup of London Fog Leopard print Chelsea short rain boots
LONDON FOG Womens Piccadill...Shop on Amazon LONDON FOG Womens Piccadill...Shop on Amazon

Summary of Tips for How to Wear Chelsea Rain Boots

Here is a quick bullet-point list of what to wear and what not to wear with short rain boots.

What to Wear With Chelsea Rain Boots:

  • skinny jeans
  • straight jeans
  • cropped wide leg jeans
  • leggings
  • dresses that are midi or shorter (+tights if needed)
  • oversized sweaters and hoodies + leggings
  • skirts (+tights if needed)

What NOT to wear with Chelsea Rain Boots:

(These bottoms combined with Chelsea boots will tend to look frumpy or odd.)

  • maxi skirts
  • long pants that can’t be cuffed to just above the boot
  • shorts
  • linen pants
  • athletic pants

What to Wear with Chelsea Rain Boots: Cute Outfit Ideas for Women

Wondering how to wear your Chelsea boots to look stylish? This section will show you examples of what to wear with your pair of short rain boots so that you look put together and not awkward!

Cuffed Skinny Jeans or Straight Leg Jeans

Do a thin cuff on your straight jeans and skinny jeans to wear them with Chelsea boots (to avoid them bunching on the top of the boots).

Another option for wearing these boots with skinny jeans is below.

Tall Socks over Skinny Jeans

I don’t have a picture of this yet, but here’s an example of how to wear crew socks over your jeans for warmth and an alternative, chic look:

Oversized Sweater or Sweater Dress & Leather Leggings

An oversized sweater and leather leggings makes the perfect combo for fall days. (Note: If you wear a sweater dress which tends to come down to just above your knees, it will look better to pair it with tights rather than leggings.)

Add a cap and your short rubber rain boots when going out!

When wearing leggings with short rain boots, it’s okay for skin to show (as long as you’re wearing the leggings as pants). For added warmth, you can wear thick socks underneath and have them peak up above your boots.

How to wear leopard Chelsea Short Rubber Rain Boots with black leggings and oversized sweater and baseball cap
This is an outfit flat lay graphic from my Outfit Calendar on the Interactive™.

Dressy Outfit + Moto Jacket

A leather jacket with structure (like a Moto style) really dresses any outfit up. That means it will elevate the casual look of your Chelsea boots to something dressier.

This is an outfit flat lay graphic from my Outfit Calendar on the Interactive™.


I’d avoid wearing these with maxi skirts since they are too bulky, but you can wear Chelsea rain boots with any skirt that is calf length (midi skirt) or shorter.

Add a pair of tights for warmth in the fall or winter. (Note: It MUST be tights. Don’t wear leggings under a skirt or dress! It will look frumpy.)

What to wear with Chelsea rain boots - leopard skirt, sweater, and denim jacket
This is an outfit flat lay graphic from my Outfit Calendar on the Interactive™.

Denim Dress or other Shirt Dress

Chelsea rain boots look great with denim dresses because both are a casual style. Add a cardigan (any length) and tights (not leggings) for warmth!

Short Rain Boots Outfit Idea for fall or winter- Denim Shirt Dress, Long Cardigan, Tights, Leopard Chelsea Rain Boots

Add fun earrings for extra pizzaz!

This is an outfit flat lay graphic from my Outfit Calendar on the Interactive™.

Sweatshirt/Hoodie and Black Leggings

Short rain boots look cute and casual paired with a cute sweatshirt and leggings! It doesn’t get easier than this outfit combo!

Flannel + Black Jeans or Leggings

There’s nothing like a plaid flannel button-down to feel like it’s officially fall or wintertime!

My 2-yr-old wanted to show you his truck 🙂

my son showing you his truck during outfit photos
Cute outfit with Chelsea rain boots - Plaid with black skinny jeans and sherpa vest
This is an outfit flat lay graphic from my Outfit Calendar on the Interactive™.

And that rounds up my Chelsea rain boot recommendations and outfit ideas!

My son would like to say: “Now go rock those Chelsea rain boots!”

Preschooler wearing women's chelsea rain boots

What to Wear With Chelsea Rain Boots and Short Rain Boots- Cute Outfit Ideas

What Is YOUR Opinion?

Do you have a pair of rain boots yet? Do you like this style or do you prefer tall rain boots?

Also, if you want links to anything else I’m wearing let me know in the comments below!

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