How To Wear Denim: Madewell Expert Stylists Share Their Rules To Dress By

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Nine genius tips you haven’t heard yet on how to shop for, wear and style your jeans right now.

Last year, we kicked off a blog series written by our in-store stylists, those wisdom-imparting, expert-yet-approachable gurus responsible for helping you find your perfect jeans. Their stories were so full of clever, inventive advice that we decided to hit them up again. But this time, we asked for their own signature denim rules—the ones they use to get dressed (and look so effortlessly cool) every day. Here, nine tips that are too good not to share.

1. “A great tailor is your BFF. Take advantage of our complimentary hemming. It’s there for a reason—so your jeans fit your body perfectly.” —Samantha, Philadelphia

2. “When it’s time to pick out a new pair of jeans, think of all the pieces in your closet that you haven’t worn lately and what you need to help you fall in love with them again. You could get another black wash. Or you could get a deep blue that would look great with that sweater you forgot about.” —Kate, San Francisco

3. “Embrace a snug fit when you buy new jeans. Don’t be afraid to size down, since they’ll break in to fit your body perfectly the more you wear them.”—Natalie, Metairie, Louisiana

4. “A fitted top is your best bet with overalls. You don’t want the extra bulk or the tucking issues of a loose style.” —Cheyenne, Philadelphia

5. “Let’s face it: Black denim is turning into the new dress pant. To look pulled together, tuck a silk blouse into a pair of high-rise black skinny jeans.” —Kess, Salt Lake City

6. “If you love showing off your shoes, wear head-to-toe denim. Accessories look great against the monochromatic palette.”—Imani, Richmond, Virginia

7. “Tucking in your top, just in the front or all around, instantly finishes any outfit, whether it’s a plain tee, a sweater or a silk top. It’ll create shape at your waist.” —Alexandra, Providence, Rhode Island

8. “A little ankle goes a long way when you’re wearing skinny jeans or straight legs. It creates the illusion of longer legs. Hello, I’m 5’2″! I know the struggles of being petite.” —Thuyvi, Germantown, Tennessee

And our favorite style tip/life lesson?

9. “Size doesn’t matter. Comfort, style and confidence do.” —Ashley, New York City

Show us the denim rule you dress by on Instagram for a chance to win a $1,500 shopping spree and jeans for you and 10 friends with a private party at a Madewell store. Get all the details here.*

Shop our entire assortment of denim here and read more from our stylists here and here.

Photography by Angi Welsch.

*Open to legal residents of the 50 United States (including DC), 18 and older. Void where prohibited. Enter contest by March 14, 2016. For Official Rules and prize descriptions, visit http://bit.ly/1kMjPce. Sponsor: J.Crew Group, Inc., 770 Broadway, New York, NY 10003.