How to Wear Chunky Chelsea Boots for Women

Hello and welcome to part two of how to wear chunky Chelsea boots for women! You can catch part one here which focuses more on shorter shaft Chelsea boots. Today we are going to move on to a taller Chelsea boot. I am a firm believer that the height of your boot is the key factor in how you need to style it. It affects the length of jean and how it fits under pants. Let’s dig in!

How to Wear Chunky Chelsea Boots – My Boots

Before I move on to how to wear chunky Chelsea boots for women, let me share what boots I will be wearing in this post. The primary pair is a really fun white, chunky Marc Fisher pair. As a reminder, you can always get 20% off anything on their site with my code LTD2206 at checkout. I also have on my waterproof Sam Edelman Laguna boots in the taupeish color. I LOVE them! In the skinny jeans section, I am also wearing an amazing $34 cream pair from Walmart! I highly recommend them too as an affordable option to try out the trend. The black pair is from target last year.

Over Leggings

First up in my list of how to wear chunky chelsea boots is the easiest and most loved – over leggings! We all love our leggings, and a taller Chelsea boot is the perfect shoe candidate for this look. They are also a super practical choice in the winter when it is cold and possibly even snowy. I love how this black and white striped tunic pairs with my white boots.

Under a Wide Leg or Loose Straight Leg Jean

Next up is under a flare, wide leg, or looser straight leg jean. Any of these are a great candidate for a taller Chelsea boot to go under. I am sharing a new example with my black jeans and also including my wider straight leg jean example from my part one post as that style of jean is idea for this type of boot too.

The KEY is you just want your jeans to be wide enough at the bottom and your boots to be narrow enough at the top that the two do not meet and cause bunching. I do think they look best under a full length pair as opposed to a cropped length.

Over Skinny Jeans

Another super easy way to style these taller Chelsea boots is OVER skinny jeans. To me, the taller shaft boots are easier to wear with skinny jeans than the shorter because it is more obvious what to do with them. Just pull them up and over your jeans! See examples below.

With a Dress

Another really fun way to style Chelsea boots is to add them to a dress! Tights or no tights, either works depending on the weather, but they add a very fun edge to a girly dress, sweater dress, etc. This particular one is from Amazon.

Styled with Joggers

Last but not least in my style tips on how to wear chunky Chelsea boots is the most adventurous – pair them with joggers! This takes me more out of my comfort zone, but I admit I really do like it! I opted for a dressier pair with a cuffed hem. Simply tuck the cuffed part into your boots. It’s really a fun look overall! Would you try this??

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