The Weekender: How to Wear Flare Jeans


After our flared jeans post, we received many happy emails from readers, delighted that they can wear the flare jeans they kept in the back of their closets.  Rarely does a trend circle back without any significant changes to it.  In this case, if you held onto all those boot cut jeans from just a few years ago, pull them out!

Jen asked, “I’d love to see a follow up / two ways showing how to style without looking like a 70’s caricature.”

Great idea.  Thanks for the post inspiration.  To keep this look wearable, pair these bottoms with updated classic pieces.  Your best bet is to go fitted to the body or pair with a jacket that hits at your hip.

How To Wear Flare Jeans1. R13 Striped Boatneck Tee, $195; 2. Diane Von Furstenberg New Bubsy Print,  $270; 3. Black Bettie Oversized Sunglasses, $10; 4. Via Spiga Farley Wedge, $100; 5. Generation Love Moto Jacket, $170; 6. Adina Reyter Pave Triangle Necklace, $198; 7.  Forever 21 Side Zip Envelope Clutch, $20; 8. Cut Away Suede Pumps, $27

Key Piece:  Paige Women’s High-Rise Bell Canyon Flare Jean, $209

For the first look, I picked a striped boatneck tee and a print DVF scarf to show that a striped tee can work as a neutral. Loop the scarf once around your neck or tie it long to mimic the line of a necklace. Go big with a pair of oversized sunglasses.  Finally, and this is so important when wearing a flare legged jean, wear a substantial shoe.  It should fill the opening of the bottom of your pant leg.  A wedge is a great choice.  Be sure the length of the jean barely grazes the ground.  Otherwise, your proportions will be off.  (The jeans pictured are too short.)

The second look is all about the jacket. When I was looking for the perfect blazer to add polish to the jeans, I came across this moto jacket and quickly put it in my shopping cart. It’s currently on sale at Saks with free shipping.  I can’t wait to receive it.

Everything else should be simple and streamline. A loose fitting silk or silk-like shell is your best bet since the jacket should stay on to keep the integrity of the look. I used gray accessories because black looked to predictable and severe. An envelope clutch from Forever 21 is a no brainer and looks much more expensive than the $20 price tag. A long pave necklace enhances the long lines of the look, and simple suede pumps add some weight to the look without being too heavy for a night out.

Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

1 Comment
  1. Thanks so much for following up on my question in this post! I’m inspired…I can’t wait to work with Christine to see exactly how I’ll do this. I’ve got the moto jacket on order, so hopefully that makes the cut!

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