21 Flare Jean Outfit Ideas Perfect for Any Season

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Honestly, who invented flare jeans? Why do they even exist on this planet when there are so many other types of jeans that are so much easier to style? It’s not that I hate flare jeans; it’s just that I don’t know how the hell to style them without looking absolutely ridiculous. As someone who’s both curvy and only 5’3″, I’m was in desperate need of some flare jean outfit ideas that wouldn’t look terrible. So, as someone who writes about fashion all the time, I knew I needed to consult the experts: celebrities and street style icons. I mean, who better to show us all how to style flare jeans than those who have personal stylists or are constantly photographed for their incredible ensembles? Taking it to the streets has never been a more successful idea.

Below, you’ll find 21 different street-style-approved flare jean outfits ready for any season. Whether it’s still 80 degrees where you are (Hello, Los Angeles.) or the weather is cooling off (I wish.), you’ll find the perfect flare jean outfit inspiration. Try some black flare jeans with your favorite leather jacket or light wash flares with your coziest sweater. If you’ve been on the fence about wearing the flare jean trend, hopefully you’ll see an outfit that makes you want to give it a try. At the end of the day, it’s all about that confidence, baby.

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Grosescu Alberto Mihai/Shutterstock.

1. Black Flares + Striped Top + Blazer + Patterned Scarf

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Lace N Leopard.

2. Light Wash Flares + Tie-Front Top

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

LAURENT BENHAMOU/SIPA/Shutterstock.

3. Mid-Wash Flares + Fringe Jacket

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Erik Pendzich/Shutterstock.

4. Light Wash Flares + Fall Hues

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Silvia Olsen/Shutterstock.

5. Mid-Wash Flares + Clashing Patterns

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Beauticurve.

6. Mid-Wash Flares + Off-the-Shoulder Top

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Wayne Tippetts/Shutterstock.

7. Dark Wash Flares + Black Turtleneck + Black Jacket

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Shutterstock.

8. Patterned Flares + Long Solid Jacket

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Cornel Cristian Petrus/Shutterstock.

9. Dark Wash Flares + Hot Pink Accents

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Shutterstock.

10. Black Flares + Bright Puffer Coat

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

ZCOOL HelloRF/Shutterstock.

11. Black Flares + White Tee + Blazer

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Stephen Coke/Shutterstock.

12. Mid-Wash Flares + Frilly Floral Top

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Cornel Cristian Petrus/Shutterstock.

13. White Flares + Metallic Top

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Shutterstock.

14. Dark Wash Flares + Denim Jacket

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Jacques Benaroch/Sipa/Shutterstock.

15. Dark Wash Flares + Gold Blazer

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Beretta/Sims/Shutterstock.

16. Black Flares + White Tee + Black Leather Jacket

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

David Fisher/Shutterstock.

17. Dark Wash Flares + Plunging White Top

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Silvia Olsen/Shutterstock.

18. Black Flares + Embroidered Jacket

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Can Nguyen/Shutterstock.

19. Light Wash Flares + Cream Blouse + Bright Color Accent

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Saira Macleod/Shutterstock.

20. Black Flares + Flow-y Black Top

STYLECASTER | A Beginner's Guide to Styling Flare Jeans

Swan Gallet/WWD/Shutterstock.

21. Light Wash Flares + Cozy Sweater

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