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Every year around the beginning of December the weather in Southern California starts to show signs of “winter” - an occasional rainy day, overcast skies, and the temperatures really taking a dip on the morning commute. This probably seems like a dramatic assessment from anyone reading our journal on the East Coast, but finding a way to feel stylish and chic in “freezing” temps. requires a little more effort when all you want to do is grab your thickest pair of black leggings, puffy jacket, and sheepskin boots. Now would be a great time to keep your Pinterest app handy, because we’re sharing five different style boards to help inspire you to dress up this winter or try a new trend whether you’re looking to add new items to your wardrobe or re-style some existing pieces. It’s amazing what a good outfit can do to boost your confidence - whether the occasion be carpool duty or a more special outing.

Fall/winter wool felt hat collection photoshoot in Laguna Beach, California featuring the Elise fedora in brown

Fall/Winter collection | Laguna Beach, California



A monochromatic look - we like the compilation of same shade neutrals (white, tan, brown) - to achieve this statement, head to toe style. Black and grey also works here - especially if you’re planning to take your look into the evening. This style tip can be applied for any season, just make sure the fabric and layers you select are appropriate for the time of year (wool in the winter, cotton and linen in the spring/summer). To take this look to the next level, add a bold red lip color - this would be perfect for valentine’s day or a ladies night. 


 Monochromatic winter style trend featuring the Leah Kiss Me Fedora in bone


Denim Skirts

Denim skirts aren’t just for country music concerts with cowboy boots. A longer, nearly midi skirt version is a great way to keep warm while adding a classic but updated look to your wardrobe. We like to pair this one with tall boots for added warmth, a beautiful belt, and a tucked in turtleneck or sweater. Save this look for your next weekend getaway - you’ll look sophisticated and feminine no matter the destination. 

An unexpected denim skirt pairs well with the Leah Elise fedora in brown



Relaxed Tailoring 

A relaxed tailored style is one of the most approachable trends for the winter season as most of the items you probably already own - a pair of good jeans and booties will take you far. If there’s one thing we would invest in this season though, it’s a tailored coat - the style is a little bit shacket, a little bit blazer - it’s modern and chic, promising to take you from day to night. It’s an easy way to look pulled together - throw it on with jeans or black leggings, and you’re out the door with minimal effort.

The relaxed tailoring trend of blazers and shackets works well with a structured Kiss Me Fedora in charcoal


Denim + Denim 

Before you write off denim on denim, this is one trend that has come back around but in a much more polished way. In order to achieve this winter style the right way, here are Leah’s top three tips for this look: choose similar shades of denim for a cohesive look, play with different silhouettes on top and bottom - if your jeans are more fitted, try a regular fit chambray shirt, and lastly - add simple accessories in similar colors to tie the look together. Wear this one to work on Fridays whether you’re in the office or working from home, you’ll look and feel ready to take on the day with confidence.

Head to toe denim with coordinating accessories featuring the Leah Kiss Me Fedora in tan



Bomber Jackets

We’re in our bomber jacket era - cropped, oversized, or fitted, it’s a fun and edgy way to step out in style. Accessorizing this look with our Smith Rancher hat in black adds just enough structure to balance the coziness of the jacket while keeping in theme with a not to be messed with vibe. Take this look to a coffee shop in the morning, a wine bar in the evening, and everywhere your busy life takes you in between. 

The Smith Rancher in black by Leah is the perfect companion piece to a classic and cozy bomber jacket.


The most important thing to think about when building your winter wardrobe and experimenting with new trends is to have fun - you’ll look good when you feel your best! We’re truly embracing the winter season here in San Diego because it gives us a chance to play with different styling options - plus with so many beautiful wool felt hats to choose from in our latest collection, we’re O.K. waiting on the sun to come back out…for now. We want to hear from you! Which of the five looks is your favorite? Feel free to leave a comment below, or share with us on Instagram @Leah_California. For any Leah product related questions, please send us an email at

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1 comment

  • Very informative! Love the looks 🥰

    Karen DeFilippo

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