The Denim Decoder: How to Pick the Right Jeans for the Right Shoes
When style’s at stake, I say bottoms up. That’s right—if you’re standing in your closet feeling the pressure to pull together an outfit, don’t start with the jeans… start with the shoes. Most of us have way more of those anyway. Your shoes determine which jean length and silhouette will look the best, and once you get that pairing right? The rest of the outfit practically builds itself.
This post is the extended version of my Ultimate Shoe Pairing Guide for Fall Jeans Outfits—including the two most flattering jean lengths for every shoe and the cool-girl jeans under $75 that work for women of every age.
Denim Decoder
The Best Jeans for Flats
If you’re looking for the right jeans for the loafers that have become so popular, I’ve tried and ranked them all, and these are my favorites. This style can be worn long or cuffed.
When it comes to flats, especially dainty ballet flats, the best jeans are ankle length with a narrow opening of less than 16“. I’m 5’4” and wearing a size 25 (regular 28″ inseam), 14″ leg opening, and 10 1/2″ front rise. This style from Paige is also available in other colors and petite sizes.
The Best Jeans for Sneakers
The best long and short denim styles have an opening between 17” and 20”. I’m 5’4” and wearing a size 25P in this video. If you’re looking for something with more of a vintage vibe and less stretch, this style from Pistola comes in petite sizes too. For long jeans with a 17-20″ opening, I love these super soft jeans from Madewell.
These jeans are always selling out, but you can get the dark wash here in petite and regular lengths.
The Best Jeans for Block Heels
The best jeans for block heels are full-length and have a wide flare opening (22”+). The pair I have on is so slenderizing and comes in petite lengths. If your wide jeans are making you feel wider than usual, chances are you are wearing them with the wrong shoes. A hunky heel look the most balanced and fills the space along the wide opening of your hemline the best
The Best Jeans for Dainty Heels
Nothing says “I look great but wasn’t trying” quite as much as the right in jeans with your favorite heels. When worn with dainty heels or stilhettos, a flare leg jean that comes in around the knee gives you a better shape than a wide-leg jean. A classic bootcut jean, with an opening between 16-19″, is my favorite combination with high heels.
The Best Bootcut
Jean Length Guide
I own hundreds of jeans and shoes, but only two jean lengths.
Cool Girl Jeans Under $75
Most jeans brands under $100 don’t list the key fit measurements online like premium denim brands, so I included the measurements on the 5 styles I liked best, so you can shop online with success too.
“Rise” – the measurement from the center crotch seam to the top of the waistband. Most of us look best with a style that sits at or one or two finger widths below our belly button.
“Opening”- this is the measurement along the hem of each leg and determines which style of shoe will look the best. Styles between 15 and 20” are the most versatile.
“Inseam” – the measurement from the center crotch seam to the opening. All of these styles are easy to hem with scissors.
Luckily, given their non-stretch nature, Levi’s are easy to hem at home without sewing. Here’s how.
5 Stylish Swaps for Women over 40
A recent detox of my overflowing closet revealed that less is more when it comes to denim, and I donated to huge bags that fit me fine, and now I actually have more stylish options because I’m focused on updated styles that serve big style. This is what I’m wearing.
Light wash jeans instead of distressed denim.
Thin whale corduroy jeans instead of coated denim, which makes your legs look like sausages.
Barrel Jean jeans instead of a baby bootcut or crop flare. You can size down in most brands. I love this style from Pistola so much, I have it in grey and blue.
You don’t have to ditch your skinny jeans, just update them with slimming jeans that have an opening between 15″ and 20″.
Dark denim for dress-up, instead of overdone, embellished styles with bedazzled butt pockets.