How To Wear A Beanie 5 Different Ways, No Matter the Weather

It's a wardrobe must-have.

A year since the start of the pandemic, and things are still far from normal. With our extended time at home, your wardrobe identity and personal style have likely been blurred by the state of the world. Something as easy as how to style winter accessories has possibly fled your mind while you're busy working from your bedroom, trying new kitchen gadgets, or attempting the latest virtual workout. 

Now, we tap into one of our favorites for cold weather and bad hair days, the beanie, and offering some accessible style inspiration. Winter accessories like beanies are the perfect pieces to dig out of the back of your closet and bring back to life.  Ahead, discover five ways to style your beanie.

Vegan Leather Jumpsuit and Sock Booties

Outfit #1

Cassandra Dittmer

I like to pair my cream-colored, organic Myssy beanie with this Nanushka vegan jumpsuit and Nomasei red sock booties. I love how utilitarian and functional boilersuits are, and they pair really well with knitted beanies.  In this outfit, you could easily be on your way to a ski trip or just headed to dinner. But what I love most is that all of these brands send a strong message that sustainable luxury and craft are achievable in a head-to-toe, cold-weather-approved look.

Printed High-Waisted Pants, Asymmetrical Sweater, and Woven Wraparound Heel 

Outfit #2

Cassandra Dittmer

When it's warm, you don’t need the beanie, but it completes the look and makes everything feel a bit sportier. I chose a Sporty & Rich beanie to juxtapose the Brother Vellies woven heels and root the whole look in a streetwear aesthetic. This ensemble is appropriate for a West Coast or Southern winter, as the pants are pretty thin, and the sweater leaves an exposed shoulder.  The warmer textures and tonal look still seal in a wintry aesthetic. 

Denim Jumpsuit, Layered Turtleneck, Puffer Coat, and Sneakers

Outfit 3

Cassandra Dittmer

This iteration of beanie styling is the most wintry of the bunch.  I love layering Nagnata's ethical and technical knit turtlenecks under my favorite Triarchy jumpsuit for added warmth throughout the season.  Myssy’s grannie-knitted beanies provide proper warmth for a no-nonsense approach to winter styling.  They always pair well with a fun, printed puffer, like the Farm Rio one (here), and high-top sneakers for an '80s vibe. 

Boyfriend Sweatshorts, Cable Knit Vest, and Boots

Outfit 4

Cassandra Ditmer

This style is a playful look for those living in warmer climates who still want to participate in seasonal style. I find that exploring with texture is the best way to achieve a wintry look no matter what the temperature is outside. The thick cable knit sweater, paired with my favorite Gestuz two-tone boots and Myssy pom-pom hat, serves as a reminder to have fun with fashion.  

A Matching Sweat Set, Western Bootie, and Trench Coat

Outfit 5

Cassandra Dittmer

Ease back into dressing up with this trench coat and beanie combination. Layer these two pieces over just about any sweat set, and you are ready to go out. I am a huge fan of pairing the Baserange wide knit matching lounge sets, Baum Und Pferdgarten’s trench coats, and AGL’s tri-toned booties with my favorite mustard Myssy beanie.  Wear coordinating gloves and a scarf with this look for some extra warmth when the sun goes down. 

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