Date with Denim

1. Fit trumps size
It’s always better to buy jeans that are a little big and have them tailored to fit than to have fabric tugging or sagging in the wrong places. But denim almost always stretches a little, so “in the fitting room, crouchdown and stand up a few times so the fabric gives, and you’ll see how they really fit,” says stylist Penny Lovell.

2. Stay simple
Nothing dates a pair of jeans faster than embellishment. A pocket doodle here, aggressively worn knees there, and you might as well be drinking a cosmo, circa 1999.

3. Shirt and shoes are required
Take your favorite flats and heels with you. “You can’t look at anything until you put shoes on,” Lovell says. They change your posture, and heels lengthen your leg.

4. Find a good tailor
A nip in the waistband and some minor hemming can make a good pair of jeans look great. Ask the tailor to use the same color thread if possible. Some stores offer it for free.

5. Be loyal
Once you find a label you like with a cut that really fits, stick with it. “I know how my favourite brand will look, and they’re consistent from season to season,” Lovell says.