Today I’m partnering with Jess Kirby for her September #monthlystylechallenge and today’s theme is “Transitional Style.” I feel like I spend a lot of time in the fall transition phase since fall weather comes so late here in San Diego and I’m always eager to ditch summer clothes.

If you feel like taking your wardrobe from summer to fall without buying a bunch of new things is a struggle, I’m currently teaching a class with my friend Conni on how to create a small capsule wardrobe of summer to fall pieces. We show you how to choose your base pieces, how to layer, how to accessorize with bags and shoes, along with ideas for creating easy, seasonal fall uniforms. You can learn more about it here if that sounds up your alley!

Now, here are 3 looks for early fall that incorporate some of my summer pieces…

OUTFIT 1: Feminine blouse + straight leg jeans + mules

This is an outfit formula I’m feeling very drawn to lately. I love the mix of the vintage-style jeans with an airy, feminine top tucked in. A top like this works well with cutoffs in the summer, and jeans for cooler weather. I completed the look with some comfy mule loafers, a lightweight sweater over my shoulders and a tote to carry all of my stuff. The jeans are a new addition to my wardrobe and I am so happy I got them. I recommend staying true to size, but know that they’re 100% cotton denim and will be snug at first and need some breaking in to mold to your body.

Similar top (also similar) / black sweater / jeans / similar mules (and the originals that they’re dupes of here) / tote / sunglasses / necklaces are Natalie Borton (currently sold out) 

OUTFIT 2: Long cotton sweater + white jeans + ankle boots

White jeans aren’t just for summer! Here I’m taking them into fall with a long cotton sweater, some tan ankle boots and a woven crossbody to add texture and pattern. These boots are brand new and I’m looking forward to cooler weather when I can finally get some real wear out of them. Use the code Natalie20 for 20% off the boots and sweater.

Sweater / jeans (in curvy here) / boots (c/o) / similar crossbody (and tote in exact same woven leather here) / bag chain / sunglasses / necklace coming soon to Natalie Borton

OUTFIT 3: Dress + leather jacket + sneakers

This is another outfit formula I can’t get out of my head. Last week I did an impromptu style session with my black leather jacket since it’s part of the Madewell Insider Sale, and I just kept wanting to pair it with dresses and sneakers. It’s a winning combination and a really great way to take summer dresses into fall. I recommend staying true to size in the jacket unless you’re in between sizes or plan to layer it with thicker sweaters.

Jacket / similar dress / similar bag / similar sneakers / sunglasses / necklace and cuff bracelet coming soon to Natalie Borton

Which of the 3 looks do you like best?

P.S. As part of the challenge, Jess will be donating to a charity of my choice, and (surprise, surprise), I’ve chosen The National Eating Disorders Association (NEDA), which is a charity I personally donate a portion of jewelry sales to to each year. NEDA is the largest nonprofit organization dedicated to supporting individuals and families affected by eating disorders. NEDA supports individuals and families affected by eating disorders, and serves as a catalyst for prevention, cures and access to quality care. Thank you, Jess, for making a donation to this organization!

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