The pairings are endless in a season with a wide range of popular denim styles and shoes. That’s fantastic if you love to mix things up, but can be overwhelming if you prefer simplicity. In today’s post, I’m addressing the most common question in my inbox lately: how do I pair straight, wide, and flare jeans with boots?
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How to Wear Boots with Straight, Wide, and Flare Jeans
My Sizing: I’m 4’10”, and my bust, waist, and hip measurements are 32″, 24″, and 36″. My inseam is 25″ (the measurement from the inside of my leg to my ankle bone). The clothes shown are unaltered and show how they fit me right from the store. I list my sizing beside each item to help you compare when shopping online. When referencing my true size, that is often the smallest option available at a brand or petite xxs/00/24. I wear a size 5 shoe.
Jeans Preferred Length with Boots
There is a lot of variation with boots and jeans pairings, but to make it simple, I focus on two things: the length of the jeans and the style of the boots.
Length of Jeans
I prefer jeans that come close to the top of my foot or the bottom of my foot. That length depends on the style of the jeans:
Straight: Slim and wide straight styles look best with boots when the jeans come close to the top of your foot.
Wide & Flare: Wide and flare styles look best with boots when the jeans come to the bottom of your foot (or bottom of your shoe if you prefer to wear this style with heels).
Style of Boots
I look for two things in a pair of boots that I want to pair with jeans: a tall, slim shaft that fits close to the ankle and a slim, pointed toe.
Tall Slim Boots: I choose boots with a tall, slim shaft to be tucked underneath the jeans. Choosing a slim-to-the-ankle style will keep your ankles from looking bulky if some of your boots still show under the jeans (like they would with straight jeans).
Pointed or Slim Toe: Your boots don’t have to be heeled or have a sharp pointed style to fit this. You can choose low-heeled chelsea style boots with a slender toe, too! For what it’s worth, the rounded-toe chelsea boots still look best to me with skinny jeans or leggings. They work with straight jeans, but since I have small feet too, I feel like the combinations just looks like little feet – big body on me – and I feel like an elongated, slender toe helps create some balance for my petite frame.
Quick Links to Boots in the Post
Styling Examples of Boots with Jeans
Here are a few examples of the popular denim styles I shared in my recent Petite Denim Series paired with boots. All of these outfits fit the two recommendations above for jeans length and boot style.
Slim Straight Jeans
These slim straight jeans from J.Crew are slim to the leg (similar to skinny jeans, but not quite as skinny), but lengthwise, they come close to the top of my foot. I paired them with casual chelsea boots with a tall, slim shaft and an elongated pointed toe.
Jeans Petite 24 | Boots tts | Jacket XXS (runs large) | Sweater XXS
Wide Straight Jeans
Straight jeans also come in what I would consider a “wide straight” style. They are not quite as wide as wide-leg jeans but have more room than slim, straight jeans. I’m wearing Madewell’s 90s Straight Jeans here. Without the boots, these jeans bunch just a bit at the top of my foot. I paired them with a pair of Madewell boots with a slim, close-to-the-ankle shaft and a pointed toe. These boots have a dressier feel to them but still have a low walkable heel.
If you’re looking for more straight jeans options, check out this post.
Jeans Petite 24 | Boots tts | White Top Small | Sweater XXS | Bag
Wide-Leg Jeans
I think wide-leg jeans look the best with boots if worn a little bit long and paired with heeled boots. Since wide-leg jeans add weight to your bottom half, the heeled boots option will give the illusion of longer legs. The jeans I’m wearing here are Abercrombie ’90s Relaxed Jeans. In extra short they’re a perfect length for me with flats, but in short they’re a great length for heels or heeled boots. I also find the high rise to be balancing and leg lengthening. The boots I chose here have a high 3-4″ heel and an elongated pointed toe.
If you’re looking for more petite-friendly baggy or wide-leg jeans, check out this post.
Jeans 24 Short | Sweater XXS | Boots tts | Bag Polene Un Nano
Flare Jeans
I apply the same concepts to flare jeans that I do to wide-leg jeans. I think flare jeans look best with boots when worn a little bit long and paired with heeled boots. In this case, I chose a pair that I can actually wear with flats as well (although they bunch just a bit at my foot in flats). I went with heeled boots with a low heel, but they still have that elongated pointed toe.
These jeans were featured in my Under $50 Jeans for Petites post.
Jeans 0P-Short | Sweater Sold Out | Boots tts
Cropped Flare Jeans
Cropped flare jeans are one of my favorite styles. I love the slim fit through the hips and thighs and the slight balancing cropped flare at the ankle. I prefer to wear this style close to the top of my foot. They pair beautifully with boots at that length. You could wear any of the boots in this post (even the low, casual Chelsea boots) with cropped flare jeans, but I chose a high-heeled style here with a pointed toe.
If you’re looking for more cropped flare jeans for petites, check out this post.
Jeans Petite 24 | Sweater Sold Out | Boots tts
Stay tuned for more in-depth reviews of boots and petite-friendly styles (like knee-high boots)!
-Brooke
