Chelsea boots have been a popular style of boot for the last couple of years and they are one of my best-selling winter shoes. They are also the shoes that I get asked the most amount of questions revolving around how to style them. Everyone wants to know what type of bottom to wear with your Chelsea boots and how to wear them. I have done 2 posts in the past on how to style Chelsea boots HERE and HERE. But today I want to take it a step deeper and dive into how to style Chelsea boots, especially when wearing different bottoms.

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I have owned Chelsea boots for the last 2 years. I won’t lie, Chelsea Boots can be tricky to work with. They are clunky and can often feel awkward with different bottoms. In my experience, it takes a lot of trial and error to figure out what bottoms to style with Chelsea boots. No pants or Chelsea boot is made the same way, so just because the boots look cute with one pair of pants doesn’t mean they will work with a different pair of pants.

Let me go ahead and address a few popular questions that I have been asked recently revolving around Chelsea boots.

Are Chelsea boots still in style?

Can I be honest? I hate getting the question “is blank still in style”? I think it’s important to stay current, but telling people that something they bought last season is out of style is just not helpful. If you love something, wear it!

I don’t think you need to embrace every trend that comes your way. You need to shop based on how the clothes make you feel. Remember that dressing polished is much more important than dressing trendy or “in style”.

With that said, if you are ever questioning if something is a quick turnover trend or something that will stick around, just ask yourself; is it practical and versatile for your lifestyle? If you feel it will add value to your wardrobe then buy it. If not, then pass.

For me, I find Chelsea boots to hold high value in my wardrobe. I live in the Midwest where the styles of cute, practical winter shoes are limited. I don’t want to wear my snow boots every day, so it’s nice to have a boot that’s practical yet also has some style to it. What I am getting at is that yes, if you ask me, Chelsea boots are still in style!

My favorite Chelsea boots

There are so many cute styles of Chelsea boots to choose from at the moment. This year I upgraded my Madden Girl Chelsea boots that I have had for the last couple of years with this pair of Nordstrom Miller Chelsea boots. I had been eyeing this pair of boots for the last couple of years, so over the summer I decided to grab them in the Nordstrom Anniversary sale and I’m so glad that I did!

There are a few features I really love about this boot. For one, they are water resistant. My last pair was not and it didn’t take long for snow to leak through. I also really love the style detailing. They have nice stitching around the soles and the toe is slightly pointed which I always find flattering when you’re petite.

Another more affordable option that I really like this season is this Universal Thread Chelsea boot from Target. I tried them on a couple of weeks ago and found them to be very comfortable. You can’t beat the price and I always find Target shoes to be of great quality!

When shopping for a Chelsea boot there are some things that you will want to keep in mind. Figure out how high of a shaft you want on your boot. I don’t want mine to be too high, because that might rub up against my calf and make it uncomfortable. Also, look for a slimmer shaft if you plan to wear them with straight-leg jeans. This will help them slide under your jeans and keep them from getting caught on the bottom of your pants.

Lastly, keep in mind how chunky of a sole you want to have. I find that a heavier sole can be harder to style. However, if you are shorter, having a thicker sole can help give you some height. Overall you just need to find a style that will work with you. I have some links below.

When it comes to styling Chelsea boots with different bottoms there is really no wrong way. I have seen them styled with so many different bottoms. Today I want to share the bottoms in my wardrobe that I am most likely to wear with my Chelsea boots.

How to style Chelsea boots with leggings:

To me, leggings are your safest bet when styling Chelsea boots. Leggings are easy to wear with boots because they tuck in nicely. I really love to wear my faux leather leggings with my Chelsea boots because I feel that they help elevate the outfit. However, you can wear these boots with whatever style of legging you like. Here are 2 ways I style my Chelsea boots with leggings.

Coatigan-small)|| Top-small || Leggings-small || Boots– 7.5

Option 1: Leggings tucked into Chelsea boot

This is my favorite way to style my Chelsea boots with my black leggings. The black leggings and black boots help lengthen my legs and create a slimming effect. I love how it looks with just a black top and a neutral color layering piece over it.

Sweater-small || Leggings-small || Socks || Boots– 7.5

Option 2: Leggings with Chelsea boots and a boot sock

Adding a boot sock with your leggings is a nice way to make your outfit feel a bit more cozy. I often wear this style on cold winter days with an oversized sweater. My favorite boot socks are from Amazon. They come in a pack of 5. I like these socks because they aren’t overly high, so they work well with all my pants.

How to style Chelsea boots with skinny jeans

Skinny jeans are my second favorite way to wear my Chelsea boots. I think the reason I still hold on to my skinny jeans is because they are such great jeans to wear in winter. They are the best style of jeans to wear with boots. My favorite pair of skinny jeans are from Express. I like my skinny jeans to hit me just above my ankle. Here are the different ways that I style my Chelsea boots with skinny jeans.

Sweater-small || Top-small || Jeans-2/short || Boots– 7.5

Option 1: Skinny jeans tucked into Chelsea boots

An easy way to style your skinny jeans with your Chelsea boots is just to tuck them into the boot. As long as your jeans are not scrunching up at the bottom, this style will look polished. For socks, I usually just wear a normal ankle sock.

Top– small || Cardigan-xsmall || Jeans– 2/short || Boots– 7.5

Option 2: Chelsea boots with skinny jeans rolled

Another way that I like to style my Chelsea boots and skinny jeans is by rolling the bottom of my jeans. I like my pants to hit just at or slightly above the top of the boot. When rolling your jeans, just try to avoid making the cuff too thick. If you need to roll them up too high, your jeans might be too long. Also, try not to leave too big of a gap of skin showing at your ankle. Try to keep the gap no less than 1 inch.

Sweater-xsmall || Jeans– 2/short || Socks || Boots– 7.5

Option 3: Chelsea boots with skinny jeans tucked into a boot sock

Just like how I wore my boot socks with my leggings, I also style them the same way with my skinny jeans. The socks give it a cozy feel on a cold winter day. The boot socks I am wearing here are the perfect length to wear with skinny jeans. I often fold the sock over at the top or scrunch them down so they don’t hit the wrong spot on my leg.

How to style Chelsea boots with straight-leg jeans

This is where styling Chelsea boots with jeans gets really tricky. Straight-leg jeans have been a trial-and-error process for me. They work with some of the straight-leg jeans in my closet and not with others. What I have found is that slim straight-leg jean works better than wider leg.

One major thing to look for when styling your straight-leg jeans with Chelsea boots is that your jeans are not competing, bunching, or getting caught at the top of the boot. This is why it’s important to look for a Chelsea boot with a slim shaft. That way it can easily slide into the pant leg. Or you can wear them with cropped straight-leg jeans that will hit right at the top of the boot.

Sweater– xsmall || Jeans– 2/short || Boots– 7.5

Option 1: Chelsea boots with slim straight-leg ankle raw hem jeans

If you are new with styling straight-leg jeans with Chelsea boots then I recommend starting out with a slim straight-leg. Something that isn’t too wide through the legs. This pair of jeans from maurices works great with my Chelsea boots. They are cropped perfectly so they hit just at the top of the boot. (If you are struggling to find the right length of jeans in your closet, try cutting them to a length you desire.)

Sweater– small || Jeans– 26/short || Socks || Boots– 7.5

Option 2: Chelsea boots with ultra high-rise straight-leg ankle jeans and boot socks under

This pair of jeans from Abercrombie is very similar through the legs to the last style of jeans, but I would say they are a bit wider at the bottom. I like the way the cropped jeans look with this style of boot, but when it is cold out, to avoid the air getting to my ankles I will wear a pair of boot socks under the jeans.

Sweater-small || Jeans– 25/regular (run big) || Boots– 7.5

Option 3: Longer straight-leg jeans

This pair of straight-leg jeans from Gibsonlook is a little longer than the other 2 pairs I shared. They still have slimmer legs, but they aren’t cropped. I don’t like my jeans to drag on the ground, having the jeans hit just below my ankle bone seems to be the perfect length to wear with boots. One way for me to get this length is to buy a pair of cropped jeans in a regular length. That way I know they won’t drag and be too long, but they also won’t be a cropped length on me.

How to style Chelsea boots with tights

When I want to dress up my Chelsea boots I will often pair them with tights and a sweater dress. I have worn them with bare legs in the past, but because I mostly find myself wearing my Chelsea boots when the weather is cold, tights are often my go-to bottom if I want to wear a skirt or dress with them.

Sweater Dress-small || Tights (similar) || Boots– 7.5

Option 1: Chelsea boots with a sweater dress and black opaque tights

Black opaque tights are my favorite style of tight to wear with my Chelsea boots. Just as I said before about the black leggings, the all-black on the bottom gives a nice slimming effect.

Sweater Dress– xsmall || Tights-small || Belt-22″-26″ || Boots-7.5

Option 2: Black sheer fleece-lined tights with Chelsea boots

Another favorite style of tights for me is my black sheer fleece-lined tights. These tights are perfect if you live somewhere that gets really cold in the winter. They feel like you are wearing a fleece blanket, but look like you are wearing sheer tights. I love how they look with Chelsea boots and a sweater dress.

Sweater Dress-xsmall || Tights (similar) || Boots– 7.5

Option 3: Colored opaque tights with Chelsea boots

This is probably my least favorite way to style tights to wear with Chelsea boots, but I did want to include it as an option. I usually choose a darker color to pair with my Chelsea boots. This cranberry adds some fun to an all-black look.

What bottoms not to wear with Chelsea boots?

I am not a fan of fashion rules, so I don’t want to rule out other bottoms completely. I believe that it’s all about finding a combination that feels right to you. However, I can share that there are a few different styles of bottoms in my closet that I don’t like to style with my Chelsea boots.

• Jeans that taper in at the ankle. I did not love how my boots looked with my jeans and pants that go in at the ankle. It just made my hips look big and I didn’t find it very flattering.
• Wide-leg pants- Both cropped and long wide-leg pants were a no for me. I felt the boots looked too chunky.
• Flares- I struggled with pairing my Chelsea boots with any pant that was wide and full-length. Maybe it’s because I’m shorter, but I just didn’t love the look.
• Joggers, sweatpants, and athletic leggings- Any pants that are too casual or have an athletic feel look best with tennis shoes.

I hope that this post is helpful for you. I will be posting a live-styling Chelsea boots on Instagram this week. If you miss it I will post a replay on my feed. I also have a reel on my Instagram so you can see all these outfits in motion!