Similar Pullover Fleece here and here | High Waist Skinny Jeans (size down one size) | Pink Booties | Fringe Tote Bag | Tortoise Sunglasses
After moving to the Midwest, many styles that weren’t in my LA wardrobe quickly became part of it. Some were easy to adopt. Others took some time to master. How to wear booties and ankle boots were the latter. It isn’t easy and makes you more frustrated than you’d ever think you could get about shoes. I’m breaking down my tips!
Ankle boots can be so incredibly cute. They can also go terribly wrong if they aren’t styled properly. When cold weather first hit last year, I spent my walk to work talking notes on how girls styled booties. In LA, it was so easy. You could get away with wearing them with skirts or dresses no matter what month it was. That window is about 2 weeks long in the Midwest. But wearing them with jeans? That’s arguably one of the most difficult style challenges out there. So here’s how I think about it.
First, find the shoe.
As I talked about in my post about the 5 best tall boots for cold weather, Nordstrom is my go to for footwear. The selection is just so good that you can get everything you need in one spot. Convenience is everything! And so is style! If you missed their fall sale, there are still tons of cute items on sale. Including tons of booties!
If I had to pick a favorite, it would be these pink suede booties that I snagged for 40% off. They come in 6 different colors if you aren’t quite ready for a statement color. The pink is sold out in most sizes so apparently y’all agree with me. So here are a few more statement boot favorites if you’re looking for alternatives! This pair is my favorite!
White Fringe Scarf | Grey V-Neck Sweater | Black Skinny Jeans | Grey Suede Booties (on sale!) | Black Sunglasses
These booties also come in 4 colors and are so slimming! I love the side slit as it really elongates the leg!
It’s just as much about the denim.
You think you don’t need another pair of jeans until bootie season. But then you try on every single pair and none of them end up looking quite right. The easiest style to pair with booties is a skinny jean that is ankle length. Anything longer tends to have too much fabric and get bulky around the ankle which isn’t a flattering look. Obviously bootcut and flare jeans are out of the question. And I don’t personally find straight leg or boyfriend jeans to be flattering with booties most of the time. It can be done with a heel pointed toe bootie but most of the time, skinny jeans are the way to go.
These high waist skinny jeans are my favorite and I’ve found they’re the easiest to pair with booties. They’re 33% off right now – just size down a size!
High Waist Skinny Jeans (size down one size) | Black Flat Booties
Every bootie is a different height. In order to avoid having 10 pairs of pants at varying lengths, the easiest thing to do is cuff your denim. The skinny jeans I mentioned above aren’t my favorite for cuffing because the underside of the fabric is dark (see above). I prefer the lighter cuff generally speaking although I definitely cuff them too!
Pink Sweater | Similar Knit Scarf in Pink | Saddle Bag | Similar Grey Mid-Calf Booties | Sunglasses
Tuck and go (with higher boots).
This is where those super skinny jeans come in handy again. With a taller boot, you have the option to cuff again or tuck them in. I like them tucked in because it slims your legs (versus bulking it up with a cuff) and also keeps you warmer!
White Pom Beanie | Caramel Turtleneck Sweater | Black Skinny Jeans | Cognac Booties (available in 3 other colors now!) | Crossbody Bucket Bag
Don’t think too much about it.
The other option when it comes to ankle boots is to scrunch the jean above the boot. The key here is to not think too much about it. The more you do, the less natural it will look. I can’t tell you how many times Matt and I have scrunched and re-scrunched his jeans on top of his boots only to realize the best scrunch was the first. Just go with it! And rock it!
So I know that was a lot of information. If I had to round up my 5 favorite booties EVER (considering fit, cut, color, and style), these would be theme! Generally speaking, Vince booties are my favorite. They are the best quality and are so stylish that you can wear them season after season, getting a lot of wear out of them. Plus, there are TONS on sale right now!
Was that helpful? What is your favorite pair of bootie or ankle boot?
*In partnership with Nordstrom.
Michelle Samuels says
I actually LOVE to wear bootcut jeans over heeled ankle booties, it looks quite flattering. You just gotta make sure u pick an ankle boot that is closer fitted so that when you walk, the top of the bootie doesnt push out against the jeans. Looks really nice with a sweater on top, and keeps your feet (and ankles!) warm.
Kimberly Smith says
Loving all of these outfits – I really want to try booties with a flared leg jean!
I love your boots collections! You look so cozy in these outfits!
A very nice selection of booties ;)
Jessica | PetiteStyleScript says
Great tips for booties and ankle boots! I also had trouble adjusting to ankle booties at first but then I found a no-show sock I loved to wear with them!
Pretty in Pink Megan (@pipmegan) says
Love booties this time of year. It’s all I wear! Also love the pink bag you have in the first look!
Megan | http://www.pipmegan.com
I love all these looks! So pretty! And you have the cutest boots and booties!!
This is such a helpful post!! Love booties and totally agree that the jeans you wear with them, seriously matter!! Those pink ones are so cute.
cute & little
I love your style! Great post and blog!
You have quite a collection of booties — I LOVE the last pair, so cute!
Beauty With Lily
Shelby Back says
I love these tips & I need those Isola booties!
kanchipuram Silk sarees says