Okay, this is a post that has been a longtime coming and also one that I created as much for me as for you. I have worked at fashion magazines for my entire career and worked with the world’s top celebrity stylist and fashion experts and editors. Yet, I still don’t know which boots to wear with different style jeans. Honestly, it’s because it’s tricky and something you have to learn but that a trained eye also helps. It’s also something that requires different types of boots and jeans and often tailoring, so don’t beat yourself up if you try to emulate your favorite influencers and your outfit doesn’t look the same. I also was really dreading putting this post together because required me to do some research as well and figure out how to put into words tips and tricks I’ve picked up on over the years from working in fashion, being on sets where celebs and models are being styled, working with fashion experts and stylists etc. Okay, you get it. I have a background in fashion and editorial, so I will (hopefully) do a good job explaining and breaking down which boots to wear with which different style jeans.
First, let’s start with some general tips for deciding which boots to wear with different style jeans that I think will really help:
The Boot Shaft to Hem Width Ratio is Key: You want a contrast between the size of the shaft of the boots (width of the top of the boots) and the width of the hem of the jeans. So if you have on a skinny jean, they look best with a wider boot worn over the jeans. If you have flare or wide leg jeans, they looks better paired with a boot with a skinnier shaft like a sock booty.
Pay Attention to the Length of Your Jeans: The length of your jeans is the next key component to getting this right. If your jeans hit at the ankle, you’re going to pick a different pair than if they hit above the ankle than if they touch the ground.
Keep in Mind the Point of the Boot: A round versus pointy toe boot matters. A pointy toe is going to elongate while a round toe is a bit clunkier.
The Height of the Boot Matters: A boot that hits just at the ankle is going to pair differently than a boot that hits mid ankle or just above the ankle. This needs to work with the hemline of the jeans.
Don’t Show Some Skin: The most flattering look will ensure that the jean hemline covers the top of the boot so there’s no skin showing between the boot and jean hem. You may need a good tailor to make this work.
And now a breakdown of which boots to where with different style jeans.
Straight Leg Jeans: These jeans work best with ankle booties and Chelsea boots. The ankle boots can be a bit tricky so you have to get the hemline to shaft width ratio right. These often look best with a bit of a heel.
Skinny Jeans: These jeans work best with knee-high boots or over-the-knee boots. You can also do a lug sole Chelsea style boot with a wider shaft, but this look feels a bit dated for 2024.
Bootcut Jeans: Bootcut jeans, which flare just slightly out at the ankle, work best with ankle boots, ankle booties, and chunkier boots.
Flare Jeans: These work best with an ankle boot or pointy-toed boot to lengthen and feel more elegant and modern.
Wide Leg Jeans: These work well paired with ankle boots, booties or Chelsea boots. With this style, you can go clunkier and with a more rounded toe or treaded boot, but they also look nice with a pointy toe heeled boot. Counter the wider leg with a heel.
Cropped Flare Jeans: These work best with a pointy heeled ankle boot that the hemline covers (no skin should show between the ankle and bootie). You need a higher shaft booty for these.
Baggy Jeans: Baggy jeans are the latest denim trend right now. With these, a chunkier ankle boot will work well.
Cropped Straight Leg Jeans: These again will work best with a high shaft booty.
And those are my top tips for which boots to wear with different style jeans. Let me know what kinds of style tips you’d like help with next.
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