If there’s one thing that defines female casual style, it’s our love for denim. Since exploding on the style scene as far back as 1873 (by a fellow you might’ve heard of, Mr. Levi Strauss), the ‘blue jean’ has become the go-to-for-almost-every-occasion item in our closets. It’s one fashion item that we.all.have. Fun fact: More than 450 million pairs of jeans are sold in the US every year and the average person owns 7 pairs (or if you’re me, it’s more like a bin full). Over the years, jeans have made quite the evolution, going from that severe, rigid denim to a mix of comfy cotton blends.

No matter your age, styles are all over the map: baggy, tailored, skinny, flares, boyfriend, ripped. (PS. If you’re over 40, we’ve got the best jeans right here) Of course, with all these fantastic choices come a slew of important style questions: Which shoes go with which jean? Can I wear a tunic with a flare? Do I tuck in my shirt if I’m wearing boyfriends? Can I wear this to work?  Answers are on their way. Here are 6 jean styles you can wear anywhere and look like a million bucks.

The Boot Cut: Your Oldest Friend

The tamer version of the flare, the boot cut is the safest choice in the jean family. Think of it as your oldest friend, the one you can always depend on, no matter what the current trend. It’s the jean that will never let you down when it comes to style and versatility and bonus, it always looks chic—with just about any shoe.

Bootcut from 7 For All Mankind, $200

Your best bet: A medium wash that sits nicely at the hips, slightly flared at the calves and hemmed to just the right length to accommodate the shoe height of your choice.

Our pick: Take it to the office on casual Fridays in a dark wash and pair with kitten heels, a blouse and blazer.bootcutThe Flare: The Curvy Girl

This sexy jean cut is back with a vengeance this year thanks to the 70s trend redux. Possibly the most flattering cut out there, the key here is to tailor it for your height and body type and always take proportion into consideration. Style tips: The flare should start just under the knee. Make sure to hem according to heel height so you don’t drag the fabric around. Tops should either be cropped, tucked in or fall just to the hips.

Your best bet: A snug high-waisted fit and darker wash will enhance all your curves while giving you legs for days.

flare final

Derek Lam flared jean, $485

Our pick: Give the 70s a modern twist with a cropped cable knit, clogs and shoulder bag—and style with some loose waves in your hair. flare


The Straight Leg: The Original

This is the classic 501 cut. The one to never do you wrong, the straight leg jean is your choice for almost every occasion. You can wear it with 99% of shoes (you can pull off knee high boots but they’re better with skinnies). This cut has a narrow leg with no flare, fits slightly looser than skinnies and should sit at our just below your waist for a pulled together look. Roll or hem at the ankle for a flattering length with any shoe.

Your best bet: A classic pair of 501s to wear with your Converse or stilettos.

straight leg final

Karl Lagerfel mid-rise straight leg jean, $90

Our pick: For a cozy-casual look, cuff the hems, pair with a loose-fit knit sweater over top a collar shirt, and grab your ankle boots and caramel macchiato on your way out the door. straight leg


The Skinny JeanThe Slim Style

Every woman has skinnies in the closet and we all struggle with how to make them look different every day. Whether we like it or not, skinnies have become the new (trendy) classic (sorry, straight leg!). We wear them with any shoe and can easily dress them up or down. Because they’re so slim, they’re the easiest cut to pull off in different colours and patterns.

Your best bet: Find them in a fabric that is snug but with a bit of stretch so you can actually breathe. Hem to just below your ankle and opt for a higher waist to suck everything in. Then wear a looser fit top.

skinny final

AG cigarette skinny jeans, $290

Our pick: Give the Canadian tuxedo the runway look with a half-tucked chambray shirt  and sky high heels. skinny


The Boyfriend JeanThe Relaxed Fit Whether you’re borrowing from him or they’re straight out of your own closet, boyfriend jeans are the best for a comfy weekend look that says: I’m not trying too hard. The new ‘go-to’ jean, this fit looks fantastic with flats and heels and makes you feel like you’re wearing sweats. Win-win. go with a cropped or fitted top to balance the silhouette.

Your best bet: They should be loose fitting but not too baggy and the hem or cuffs should be above your ankle. Let them fall to your hips and add a belt if necessary, for the ultimate comfy feel.

boyfriend final

Elliott distressed boyfriend jeans, $145

Our pick: For an uber street style look, pair them with some printed oxfords, a white tee and cropped leather jacket. boyfriend


The Cropped Jean: The Cutie Perfect for when you need to go somewhere eventful but not too dressy: happy hour meeting, wine tasting, a potential-but-not-planned run-in with your ex. Ideally in a soft fabric, this cut should be cropped to just above the ankle and sit at your waist or hips. As for fit, make sure it’s comfortable—not too loose or tight.

Your best bet: Opt for a soft black pair that will give you the ultimate in style flexibility.

cropped final

Frame black cropped denim, $265

Our pick: Keep it simple and sophisticated with some ballet flats and a cute cardigan. cropped


What is your fave style of jeans? How do you wear them? 

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About the author

Despina Danishwar

Media and fashion have both always been present in my life, and I'm extremely fortunate to have worked in both industries. I've gone from Technical Director to Wardrobe Consultant at The Weather Network and a buyer's assistant at TJX Canada. I'm currently in my happy median...Public Relations. I'm happy to also be called a wife and mommy to two little divas

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