How to Shop for Denim, According to Stylist Allison Bornstein

In Wear it Well: Reclaim Your Closet and Rediscover the Joy of Getting Dressed, author and stylist Allison Bornstein lists the nine universal pieces that she believes belong in every wardrobe, styling ideas for each, and how these pieces work within the framework of her famed Three-Word styling method. Ahead, her tips for an all-important closet staple: denim.

Finding your perfect pair of jeans is like dating. You might have to search a little, but it only takes one. A great pair of jeans makes you feel amazing, like the best version of you. I know it can be discouraging to try on a million pairs of jeans that don’t work, but prepare yourself for that possibility and commit to staying with it until you find the right one. My advice when it comes to trying denim is more is more — try as many pairs as you can. And no matter what your Three Words are, a pair of jeans that you just love to wear is essential. 

1. There are very few occasions, except for the most formal, where denim would be inappropriate. Designers even show jeans with their runway collections these days. But how you style your denim makes all the difference. You can wear the same vintage Levi’s with a T-shirt and sneakers for a walk in the park or with chic slingbacks and a silk blouse for a work meeting. 

2. Denim amplifies the casualness of any look. When worn with an amazing sequin jacket and heels, denim brings your style back down to earth.

3. In the workplace, you can dress denim up a bit to feel polished. I love pairing it with a blazer for work. I always add a belt to give that finishing touch. 

4. Americana. Classic. Preppy: Try denim on denim! Wear your jeans with a soft chambray button-down and a pair of loafers. If denim on denim feels too intense, add a white tee under your denim shirt and unbutton it a little or wear it open. This will break up the look a bit and make it feel less intense. I like when the denim colors are similar, but if it feels too matchy, try a lighter denim shirt with some dark denim jeans. 

5. Bourgeois. Tailored. Academic: Go for straight-leg denim with a crisp white button-down and add a black cashmere sweater on top. Tuck in the shirt so only the collar is visible to give a polished look. Top it all off with a houndstooth blazer and a pair of kitten-heeled booties for a prim and proper spin. 

6. Trendy. Glam. Sporty: Choose high-waisted denim with a high-neck bodysuit and leather bomber. Finish it off with gold hoop earrings and a pair of chunky-soled boots.

7. Sofia Coppola would wear high-waisted straight-leg jeans with a striped sweater and a pair of ballet flats. 

8. Penny Lane would flaunt flared denim with an embroidered blouse, a shaggy jacket, and platforms. 

9. Fran Leibowitz would choose vintage Levi’s, a white button-down shirt, a blazer, and boots.

Shopping for Denim

How high should the waist be? Should you get a wide leg? When you are choosing your jeans style, go for what suits you. As I’m writing this book, skinny jeans are out. I don’t think this means that you can’t wear skinny jeans. But maybe this is an opportunity to try something with a slim leg that isn’t tight around the ankle. Who knows, you might love flares. I want people to wear what they like and what makes them feel amazing, but I also love it when people can have fun and not be afraid to try something new. When we take baby steps, experimentation is easier. Take it slow. Give yourself a second. If you still love your skinnies, then great — wear them. Everything comes back around.

When shopping for jeans, create a denim dressing room in the comfort of your own home. Bring home a few different sizes and a few different styles and have a denim party. Try on your denim with all kinds of different tops, jackets, and shoes to get a solid sense of what works with what you already own. Remember—returning clothes is just plain annoying, and a place where you can lose steam. Get all the sizes you’re interested in at once so you can return everything together instead of spending time going back and forth.

Excerpted from Wear it Well: Reclaim Your Closet and Rediscover the Joy of Getting Dressed by Allison Bornstein. Published by Chronicle Prism, an imprint of Chronicle Books. Copyright © 2023 by Allison Bornstein.