It’s the end of summer and fall is for sure on my mind. Taking a wardrobe seamlessly from one season into the next is a bit of an art, especially if you don’t plan to do any (or much) shopping. One of the many reasons I do these style sessions is that I’m passionate about helping you curate a wardrobe that truly serves you and your lifestyle, reducing the need to compulsively shop because you feel like you have “nothing to wear.” For those of you who want even more guidance in this area, don’t miss the new style class Conni Jespersen and I are teaching on this topic! You can learn more about that here.

One of my all-time favorite wardrobe items is a blazer—it’s masculine, structured, cool, effortless and it works for most of the year here in San Diego! Today I’m styling an oversized black blazer 8 different ways with some of my favorite summery items to show you how to easily transition into the next season as the temperatures (hopefully!) start to cool down. The one I’m wearing in each look was gifted last year from Amour Vert and is currently sold out. I recommend trying this similar one or this sweater one for a similar look.

All of the jewelry I’m wearing is from my shop—14K Gold Hoops, 14K Gold Textured Huggie Hoops, James Link Chain Necklace, Chloe Coin Necklace.

First up, a breezy white summer dress. For summer, I wore mine with sandals and a belt bag, and as we transition into fall I’ll add a belted blazer, mule loafers and a patterned leather bag to add some visual interest. I love the way the blazer adds masculinity and structure to contrast the very feminine, flowy dress.

Dress (c/o, 20% off with Natalie20) / Similar bag / Bag chain / Similar shoes

Slip dresses are so versatile and really amazing pieces to use from season to season. They’re so easy to layer with! While you absolutely could belt the blazer like the first look, I wanted to create a really casual feel to balance out the sexiness of the leopard slip dress. Sneakers keep it really grounded. This outfit would be great for a day with my kids because it’s comfortable and practical (and the pattern on the dress hides stains!).

Similar dress / Sunglasses / Similar sneakers (also similar) / Similar bag

In the summer I wear my tees with shorts or skirts, and my jeans get paired with sandals and lightweight tops. Here I tucked in the shirt, layered the blazer over it, and added in a bold ankle boot and a pop of color with the bag to make it a bit more interesting. This look is 100% inspired by one of my personal style icons, Anine Bing.

Tee / Similar jeans (go down a size!) / Bag (different red option) / Boots (c/o)

White jeans are a year-round item for me personally, and I love styling them for fall and winter. Here I paired them with the blazer and a cotton sweater, plus leopard mules and a classic saddle bag. I’m 33, but I could easily wear this outfit when I’m 73. It’s timeless and classic and ageless.

Sweater (c/o, 20% off with Natalie20) / Jeans (c/o, curvy version here) / Mules (20% off with Natalie20) / Similar bag

Here’s a look featuring a black tank I’ve been wearing this summer, and another white denim idea for fall. I love the way python print looks with a black and white outfit and keeps it feeling fresh and edgy.

Tank (and similar) / Jeans (c/o, curvy version here) / Similar shoes (mule version here) / Similar bag

Here’s another classic look and an easy way to take your summer stripes into fall. I have a few cotton striped tees in my wardrobe because they are so versatile and always in style. This top actually has puff sleeves, but they’re not so poofy that they affect the way the blazer fits.

Top / Jeans / Similar bag / Similar shoes / Sunglasses

Denim shorts and white button downs are two favorite summer items for me. Here, I bring them into fall by pairing them with some d’orsay oxfords, the black blazer and a leopard clutch for a little pattern.

Shirt (and similar) / Shorts (c/o, and similar) / Shoes / Bag

For this last look, I worked with my favorite little black dress for summer. I wear this on hot days when I don’t want anything clinging to me, and it works so well for transitioning to fall. I love the black blazer over it for an added layer of warmth as the days start to cool down. I also swapped out my summer sandals for pointed toe loafers, and added a patterned leather bag to add depth, texture and detail to the otherwise minimalist outfit.

Similar dress (also similar) / Similar bag / Bag chain / Loafers (c/o, and similar) / Sunglasses

Hopefully that helps you see how easy it can be to use summer favorites for fall weather! If you need more blazer inspiration, I started a Pinterest board dedicated to them and will keep updating it all season long! You can check it out here.

Do you have questions about transitioning your summer clothes into fall? Leave them below!

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