My friend Kendra—who recently moved from New York to northern California (break my heart!)—always has inspiring style. She looks laid-back, but her outfits have a bit of a twist. Here, she shows the four ensembles she’s wearing most this fall… …

Look #1: Similar sweater, jeans, fedora, flats (update: now sold out everywhere! but there is a similar pair here)

“I was psyched to find these flats. They’re feminine but still have that loafer shape I was looking for. I wear them with absolutely everything. I’m trying to change up my silhouette a bit—I’ve worn skinny jeans for like 10 years now so I finally got a pair of boyfriend jeans. I like the loosey goosey look. And this hat is my staple; it can dress up any outfit. When I’m wearing it, people think I’m a designer! A guy hit on me in Whole Foods. Maybe the hat makes you look mysterious. I was on the edge of buying it for years; I kept mentioning it to my friend, and she ended up buying it for me as a gift before we moved.”

Look #2: Similar tank, skirt, bracelet, clutch, booties

“I don’t usually show a lot of skin, but I love this trend of a high-waisted skirt and knotted shirt and just showing a tiny bit of tummy. I’m trying to get away from always wearing black, and I’m feeling inspired by burgundies this season. For styling, I pretend the skirt is a pair of high-waisted jeans, so I’d pair it with things like a cropped sweater or a button-down shirt with that front tuck that everyone’s doing.”

Look #3: Men’s cardigan, white shirt, black jeans, flats (update: now sold out everywhere! but there is a similar pair here)

“I love these Target jeans—I’ve had them for six years, so the hole in the knee is real! Last spring, I had an overwhelmingly busy few weeks, so one night, I decided to have a glass of wine and line up a bunch of outfits. I was feeling it that night and was being more creative with colors and combinations. And I ended up having the smoothest three weeks after that! Every day I liked the way I looked and didn’t have to make any decisions in the morning. I’d love to do that again.”

Look #4: Overalls, tank, bracelet, Wayfarer sunglasses; floral toddler dress

“Overalls are a new thing for me. I haven’t been brave enough to wear them off the beach—still can’t decide if they’re a yes or no! One fun way to try out new pieces is to do clothing swaps. It’s a great motivation for cleaning out your closet. You spend a great night with girlfriends and go home with a couple pieces you’re excited about. Win win.”

Thank you so much, Kendra! Your style is amazing. And I miss you:)

P.S. How Kendra gets such awesome hair, and our friend Gaby’s three fall outfits.

(Photos by Maria del Rio for Cup of Jo)