Layering Like a Pro

Cozy, confident and bold.

How to stay comfortable and confident this fall

Fall is that season where you’re navigating cold mornings, warm afternoons, and chilly evenings. My Aunt Janet just told me how frustrating she finds it to figure out what to wear for such unpredictable weather. So I thought I’d help her (and you) out with some tips on how to dress comfortably and confidently, no matter how much the temperature swings. Layering is key, but not just any layering. This is about staying comfortable and authentic so you can feel good in your skin and focus on what matters.


Start with the flour

Think of your wardrobe like baking. Without the right foundation, everything else falls apart. You wouldn’t buy a bunch of fancy toppings without making sure your cake is solid, right? In fashion terms, this means investing in reliable, comfortable staples you’ll wear over and over.

Your jeans, for example. They’re the “flour” of your wardrobe recipe. Don’t skimp here! Invest in a pair that makes you feel great, no matter what. Whether you’re running errands or heading to work, your jeans should be a go-to piece that’s both comfortable and versatile.

If you’re unsure about your base colors, I explain how to build a wardrobe foundation that complements your unique palette in this post on color analysis. It’s a good starting point for creating a wardrobe that feels authentically you.



Layering essentials

It’s time to start layering. Functionality is key here. People often forget that when layering in the fall, they’ll be adding a coat on top of everything else. That’s why buying coats in the right size is so important. A too-tight coat not only feels restrictive but can throw off the whole look, making it feel less polished and put-together.

Ana Harris, a personal stylist, carefully selecting outfits from a clothing rack, dressed in a black jacket and bold white necklace, with a focused expression.

Choose looser outer layers so you can move easily, adjust to the weather, and layer without feeling uncomfortable. You want to feel ready for whatever the day brings, while looking effortlessly composed.

Match your hair with a cozy flair

Let’s talk boots. Fall boots should be functional and reliable, something you can wear all day. I always recommend low block heels or flats because they’re practical for everyday wear. My tip: Choose a pair in a tone that matches your skin or hair color. That way, even if your boots don’t match anything else you’re wearing, they’ll still match you. It’s about creating a look that feels authentically you and effortlessly cohesive.

And don’t forget about scarves. They’re a perfect fall addition. If you choose one in a color that matches your hair, it can tie your whole look together in a way that feels intentional without looking overdone. It’s a small but powerful detail that pulls everything together. Not sure what to pick? Check out these perfect everyday scarves here to find one that complements your fall look!

Sprinkle in the fun

Now that your base and layers are in place, let’s talk accessories! When it comes to fall, steer clear of bulky necklaces or long earrings that tend to get tangled in scarves and jackets. Instead, opt for fun socks, a bold lipstick, or even a stylish pair of sunglasses. These little touches can add personality without the hassle, allowing you to stay comfortable and confident.

Feeling good in your skin

Fall fashion doesn’t have to be complicated. It’s about finding that balance between comfort and authenticity so you can focus on what really matters: feeling good in your skin and showing up for the things that make you feel fulfilled. Start with a solid foundation, add some functional layers, and sprinkle in a few personal touches that feel like you.

A special thanks to Janet for inspiring this post! Now, I’d love to hear from you: What are your go-to fall pieces? Let me know in the comments how you’re staying comfortable and confident this season!

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