Chelsea Boots: How and Where to Wear Them

Styling Chelsea Boots (Boot Camp)

Welcome to boot camp! All week I’ll be talking about different styles of boots. Today we’re talking all about Chelsea boots – from what pants to wear with them, how to style them, and where to wear them. 


I know you know about Chelsea boots, but today I wanted to dive in deep and create this post to be your Chelsea boot guide.

I’ll explain how to wear Chelsea boots for different occasions, what pants, skirts, and dresses to wear, what socks to pair them with and so much more.

I’ll break down everything you ever wanted to know about Chelsea boots!

My favorite chelsea boots ever

These Caslon Chelsea Boots are my all time favorite chelsea boots. I’ve looked at and tried on so many different ones, and nothing compares to THIS PAIR.

They’re extremely comfortable (they’re stiff at first but soften beautifully after a few wears), and are a great height and shape, and  nice and narrow on the shaft so they don’t make your ankles look bulky. Get your true size.

They come in a few different colors and they’re on sale, but if you need a more budget friendly pair, THESE ONES look similar and about half the price.


What socks I wear with Chelsea Boots

I wear THESE BOOT SOCKS almost every time with my Chelsea Boots. They’re super comfy, not scratchy, and come in a ton of colors. My favorite are the “5 Pairs Solid Color” option. They say hand wash, but I’ve machine washed mine a million times and they’re held up great.


Where to wear the boots

I wear these boots literally everywhere and anywhere.

  • They’re great for traveling cause once they’re broken in, you can walk in them all over the place. If you’re worried about them rubbing on your lower legs while you walk, wear the boot socks, which come up about 1″ above the boot and will protect your leg.
  • The lug sole makes them great for walking in snowy conditions. They don’t slip around.
  • The waterproof pebbled leather makes them great for wearing in snow and rain.
  • Because the Chelsea boots have a slim shaft, they’re great to wear with skirts and dresses to church or date night cause they don’t make your ankles blocky.

What kind of pants/jeans/lengths can you wear with Chelsea Boots?

These Chelsea boots have slim shafts, so they work really well with literally any pants:

  • straight leg jeans
  • cropped jeans
  • wide leg jeans
  • full length jeans
  • skinny jeans
  • leggings

If you’re wearing cropped pants or jeans: 

  • Keep the gap between the top of the boots and hem of your pants about 1″ or less.
  • If your cropped pants are longer and cover the top of the boot, that’s great too. 1-2″ over the boot is great for crops.

If you’re wearing full length jeans or pants:

  • Don’t let the pants drag on the ground
  • They shouldn’t be shorter than 1 1/2″ off the ground

Tips for wearing with skirts and dresses

I have a few posts about wearing Chelsea boots with skirts and dresses!


Dressed up and dressed down 

I’ll show you a few examples of dressing Chelsea boots up and down. You can wear them with dresses, skirts, pants, and dark wash/black jeans for a dressier look, or dress down with casual dresses, joggers, light wash jeans, and leggings for a casual look.




puffer vest chelsea boots leggings
pullover zip black zella joggers chelsea boots
Light wash jeans tan Chelsea boots white button up utility jacket olive green
light wash jeans gray sweater




black jeans brown sweater Chelsea boots
Gray wide leg jeans white tee trench coat tan Chelsea boots
colette Maeve pencil skirt chunky gray sweater ankle Chelsea boots
black chelsea boots outfit with skinny jeans and puffer coat
black leggings with hoodie and black chelsea boots outfit




pleated leopard skirt with chelsea boots and black turtleneck
Sweater dress with boots
chelsea boots outfit with sweater dress


I hope this is helpful! I’ve got another boot breakdown tomorrow on the blog – don’t miss it!





  1. Elva Palmer says:

    Hi Merrick, i love your instagram, So informative!
    I’ve been eyeing a Chelsea boot but not sure if i can pull it off. I’m a young 57 year old and just WONDERING if this is a younger person’s boot.
    I’d love your perspective.
    Thank you and keep ip the amazing work!!

  2. Emelye says:

    So helpful, Merrick, thank you! one follow-up question … what socks do you wear for THE “hiDDEN Sock” look? PS I ordered the Century star pack!

  3. Tiffany says:

    I finally bought a pair of “THE” boots based off your recommendation. What socks do you wear for a ‘no sock’ look? Keep SHARING outfit ideas with these boots—i need the INSPIRATION.

Leave a Reply

powered by chloédigital