The Jeans & Booties Guide - See (Anna) Jane. (2024)

We all know that finding that perfect pair of jeans can sometimes feel like searching for a needle in a haystack. The options are endless from slim-straight jeans to flare, distressed to classic denim, light wash to dark wash, etc. The past few seasons, the industry has really been hammering home that skinny jeans are out (and to that, I’ll always keep a few pairs of skinny jeans on hand because I think they’re classic even if I don’t wear them as much), a lot of us are wondering how to style booties with straight leg jeans for fall.

Consider these 3 factors when shopping for jeans

• Body shape: Understanding your body shape is key to finding jeans that flatter your figure. The rise on your denim jeans is something that is especially important. Try on low, mid, high and ultra high rise to see which one or two suit you best. Rises don’t go in and out of style as much as jean silhouettes do. Personally, I have been loving a mid to mid-high rise! Super high rise are uncomfortable (and usually too short on my tall frame). If the cut is looser, I actually don’t mind a lower rise–not 2002 low but lower than I’m used to.
• Stretch or no stretch:Jeans with little stretch (usually containing spandex or elastane) are incredibly comfortable and offer a great fit that hug your curves. A great option is Good American jeans! On the other hand, if your perfect pair of jeans is a pair that holds everything in place and doesn’t stretch or get baggy throughout the day, then rigid, vintage-like denim is the way to go. Again, for me–I’m a no or minimal stretch kind of gal. I just love how they WEAR.
• Versatility: Ideally, the jeans you buy should be versatile and able to pair with different tops and shoes. It’s important to think about how these jeans would fit into your wardrobe since quality jeans can be an investment. When deciding on a pair of jeans, see how they look with a pair of booties and a pair of sneakers to ensure you can dress them up or down.

Tips for styling straight leg jeans with ankle boots

• Jean length:Decide whether you prefer jeans to be above the ankle or below. Inthis post, I styledskinny jeans with ankle boots and the jeans above the ankle. With straight leg jeans, I prefer just below the ankle. This way you can wear your jeans with heeled shoesor sneakers/flats without them dragging on the floor. Jeans that are baggy at the hem are truly having a moment, so if you’re into that, go for it! But my go to length is grazing right below the ankle bone.
• Leg openings: The main thing that changes the game is the leg opening! Choose jeans that have have a slightly wider leg opening for pairing with ankle booties. You don’t need wide leg jeans, just true straight leg jeans that aren’t slim-straight or have a tapered ankle. This allows your jeans and booties to work together, not against each other. Have you ever had jeans that constantly got stuck in your booties and you needed to pull them out? Or your jeans bunch up on your booties? We’re trying to avoid that!
• Selecting the right booties:Along with the last tip, finding the right booties is just as important. It’s not about whether they’re a pointed toe boot or rounded, but the ankle style. Try a pair that hugs your ankle and sits higher on it, too.This will help you wear booties with the jeans you may already have thatdohave a more tapered ankle. As you grow your denim collection and pay attention to leg openings, you’ll start to see that the wider opening will give you more jean/bootie combos that look pair beautifully together.

Where to shop for quality jeans

Along with a number of other denim brands I’ve shared, these retailers are size inclusive and a great place to start your search!

• Abercrombie (offers sizes 23-37, extra short to extra long, and a curvy line with an addition 2″ in the hip and thigh)
• Madewell (offers petite, plus, standard and tall jeans from 00 to 28W)
• Universal Standard (offers sizes 00-40)

Lastly, did you know that your inseam should also vary depending on the leg style/silhouette? Check out my inseam guide (exclusively in my Substack newsletter here) if you need help finding the best inseam for your height and jean style!