In my high school days and early 20s, bootcut jeans were my skinny jeans. They were the style I felt the most comfortable in, and it was hard for me to switch to skinny jeans when bootcut was out and skinny was in. Bootcut jeans go with a wide range of shoes, your ankles will always stay warm, and your socks won’t show. Plus, the cut is universally flattering. I, of course, still love straight jeans, cropped flare jeans, and wide-leg jeans, but I’m seeing a resurgence in the classic bootcut style. Trends are trends, but I can see more bootcut jeans in my fall wardrobe.
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Casual Outfits for Fall with Bootcut 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.
Wit & Wisdom Bootcut Jeans
In high school, I didn’t wear petite bootcut jeans. I wore super high heels with my jeans or, of course, dragged them across the ground. Times have changed, and now there are petite options that not only work with low, comfortable heels but can also work with sneakers and flats. This pair from Wit & Wisdom is true to size; I’m wearing them in Petite 00. They are stretchy and true to the Wit & Wisdom brand; they have a stretch band at the waist for comfort and fit. The measurements from Petite 00 are 9″ rise and 28.5″ inseam.
Cropped Sweater
This Free People sweater has a roomy and boxy fit. The cropped length hits the top of my jeans perfectly, and I love the balance it gives without having to tuck in my top. For warmth and comfort, I’ll be layering this sweater over a long-sleeved t-shirt all season long. I’m wearing it here in XS, and it has an intentionally oversized fit. I cuffed the sleeves as well. I paired the jeans with the walkable Dimes boots from Madewell. The boots have a 2″ walkable heel and are comfortable for all day wear, but the pointed toe still gives the boots an elevated look. You can find a video review of the boots here.
Jeans Petite 00 tts | Sweater XS | Boots tts | Bag Polene Un Nano in Textured Tan
Crochet Jacket
This crochet jacket isn’t a perfect fit, but it is unique and beautiful, so I made an exception for it. I’m wearing it here in XS, and it fits me well enough, but it is a little wide through the shoulders and long through the arms. I love it layered over a long-sleeve t-shirt, and I think it’s a perfect complement to bootcut jeans.
Jeans Petite 00 tts | Jacket XS | Top XXS (top is sheer) | Belt | Boots tts | Bag Polene Un Nano in Textured Tan
Utility Jacket
At this point you may be thinking, another oversized item? But hear me out, this utility jacket is oversized, but I love the fit! If you’re willing to cuff the sleeves, the oversized fit makes for a jacket that is cozy and long enough to pair with leggings and jeans! I’m wearing the jacket here in XXS and it has a roomy fit, perfect for layering. I paired the jeans with the Justine boots from Madewell here. Another low-heel option that is walkable and comfortable. I paired them with the sling bag from Madewell in a similar shade of brown. This bag is a great size, and the strap adjusts short enough for petites, but it does have a good amount of excess strap hanging when you shorten it.
Jeans Petite 00 tts | Sweater XS | Jacket XXS | Boots tts | Bag | Boots tts
Fleece Jacket
If you’re looking for quality outerwear with a great petite fit, I recommend checking out L.L. Bean. They have a sizeable petite selection of classic styles that will last in your wardrobe for years – including this fleece jacket. I’m wearing the jacket here in Petite XXS, and it has a true-to-size fit. The fleece is thick and warm and the jacket still has room to layer. For a relaxed look, I put sneakers on with this outfit. The jeans are still short enough for sneakers, and I love high-top sneakers paired with tall socks in the fall and winter. It’s so cozy and warm!
Jeans Petite 00 tts | Jacket Petite XXS | Sweater XS | Sneakers tts
You’ll be seeing more bootcut jeans in my fall posts; stay tuned!
-Brooke
