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How To Style Chelsea Boots (In Every Season)

So last year Chelsea boots seemed to be the “it” shoe and they are still very popular and will again be a closet staple going into fall and winter. That being said, I wanted to do a post on various ways to style them. I personally have found them to be my most worn shoe during the colder months but I’ve also caught myself wearing them during the spring and summer, especially when there is a chance of rain. A lot of the brands have made their Chelsea boots waterproof or water resistant, so they make for really cute rainboot swaps as well. Hopefully this post shows you how versatile they are and will encourage you to grab a pair for this fall if you don’t have a pair already! Also, I’ve linked various styles below but the ones I am wearing in the photos are the Laguna Pull On Booties and Hayle Platform Chelsea Boot. Both fit TTS. Ps. The Laguna Pull On always sell out fall and winter so if you have your eye on them purchase now!!

Styled with skinny jeans

So don’t get me wrong, I do tend to gravitate more towards a staight leg jean these days, but I still don’t think you can go wrong with a classic skinny jean. In fact, I’d argue that during fall and winter especially, a black skinny jean is a closet staple (will link these here, fit TTS). And you can see that a Chelsea boot works great with this style. I personally prefer that the jeans and boots are the same color (black) as I think it gives everything a more streamlined look.

Styled with sweats/joggers

Next up, joggers/sweats. I’m all about being comfortable, and if I can find a way to elevate joggers I’m here for it! I feel like Chelsea boots look really cute with joggers and a pair of chunky/thicker socks underneath. I paired the joggers though with a more fitted, neutral top to make the whole look feel more put together. The other way I would have styled the boots with joggers were if the joggers were part of a matching set. This way, the whole look feels more intentional vs. sloppy/just thrown together! Linking these joggers here, fit TTS.

Styled with straight leg jeans

As we transition into fall, I love the Chelsea boot with a wide, straight leg (cuffed or uncuffed) jean paired with a more fitted top, like a crop. As we move into the colder months, I’d swap out my cropped tank for a cropped sweater or a more fitted sweater that I could do a French tuck with. Linking jeans here, they fit TTS.

Styled with shorts

Last but not least, shorts! I feel like the assumption is that Chelsea boots can only be worn during the colder months, but I disagree! I think they look really cute with shorts because you can really see the boot/they can make more of a statement, but they are also perfect for rainy days. I know rain boots have come a long way, but I personally am not a big fan. They are big, clunky, and don’t really add anything to an outfit. I feel like a lot of Chelsea boots now are made with a material that is waterproof or resistant so they are a great alternative to rain boots that you can wear in rain or snow. They are also easier to pack when traveling too because they don’t take up as much space as a standard rain boot, and you can clearly style them with a lot of other outfits! Linking shorts here (fit TTS) and button down here (wearing a medium); similar here.

Also, here is a reel I did with 3 other ways to style them, especially for heading into fall!

Alright guys, I hope this helped give you some ideas on different ways to style Chelsea boots! Also when in doubt, Pinterest is a great resource for finding different ways to style them. So if you’re still feeling stuck, I’d head over there!

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