I am a believer in owning your personal style, saying what you mean, asking for what you want, living authentically and the power of simplicity — in fashion, and in life.

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10 Rules for Effortless, Everyday Style

In this series, I share some simple tips for leveling up your daily looks.

Today’s style session is focused on a surprising new favorite wardrobe item: these python loafers (more sizes in stock here!)

First things first, I have to admit that I was hesitant to jump in on the python/snakeskin trend. I went ALL IN on leopard over the last year because it’s so timeless and the colors really work well for my skintone, but snakeskin felt a little more trendy and tends to be cooler tones that don’t always look best on me. Fast forward to my Madewell event where I got to select an outfit to wear for the popup. I had totally overlooked these loafers online, but when I saw them in person I knew they would seamlessly fit into my wardrobe. I love that the color is more of a black and tan instead of gray and white!  (Sizing note: they’re pretty true to size, but if you’re on the fence or have wider feet, I’d go up 1/2 size)

Here are 5 ways I’ll be wearing mine this fall—in all of these looks I’m wearing the Jaime Hoop Earrings in Brass Snake (so fitting, haha). They’ll be available on November 6th at 9am PT as part of the upcoming Holiday Collection. Scroll down for links and outfit photos, or see the styling in action over on my IGTV channel.

Coat (c/o) / Blouse / Jeans (c/o) / Similar Bag / Bag Strap

This is the look shown at the very top, but with a coat added for a layering option. The blouse is pretty sheer, so that’s just something to know if you’re thinking about getting it. I sized down in the jeans for the curvy style I’m wearing and they’re a perfect fit. The coat runs a bit big so I sized down.

Dress / Bag (c/o)

Oh hello, fall dress of my dreams!! I’m generally a pants person, but when I find a perfect dress I can’t resist! The length feels perfect on me (I’m 5’4″) and I love those sleeves. Also, I discovered after I got home that the tie around the neck is removable—you could even use it as a belt! So many possibilities.

Blazer (c/o) / Tank / Jeans / Bag (and similar)

You can see more of this gorgeous blazer right here! It runs big, so size down. The jeans are so soft and ridiculously comfortable. They are an investment, but a really great classic pair of skinnies if you’re looking for some good quality, ethical denim. I stuck with the same size I wear at Madewell and Everlane for these, and for reference they have a 9″ rise, which I consider to be more of a mid-rise fit.

Shirt (c/o) / Sweater (c/o) / Leggings (also in plus) / Bag (c/o)

Easy and comfy fall outfit right here—and totally works for you postpartum mamas, too (just lift the shirt and you’re good to go with breastfeeding!). The leggings run small, so I sized up a size. I sized down in the white shirt since it’s really oversized, but stayed TTS for the sweater. It’s a turtleneck, but I rolled the neck down a bit to show off more of the white collar on my shirt.

This is the look that inspired me to buy the loafers! I selected the sweater, jeans and loafers to wear to my pop-up event and loved how it all came together. It felt like a perfect mix of effortless French girl and California cool. The jeans run big, so size down 2 sizes from your Madewell size! Also note that these are cropped jeans, despite not being explicitly labeled that way. This is regular length, which has a 26″ inseam. If you’re taller than 5’4″ I’d order the tall length. I also sized down in the cardigan so I could wear it like a top.

Have you hopped on the python train yet? Which of these looks is your favorite?

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5 Ways to Wear Python Loafers this Fall

Read the Comments +

  1. […] Python loafers* (also price matched here if they’re out of your size at Madewell. Here are some styling ideas.) […]

  2. Sienna says:

    I just recently found your blog/instagram and truly you have inspired my style SO much. I live for your updates and am so thankful!!

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Hi, I'm Natalie

I am a believer in owning your personal style, saying what you mean, asking for what you want, living authentically and the power of simplicity — in fashion, and in life.

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