I Plan to Wear My Summer Wardrobe Through Fall Thanks to These 5 Items
I have to admit that as excited as I am for the upcoming fall season, I'm not quite ready to part with my favorite summer pieces. Don't get me wrong—I'm beyond ready for the heat to subside and let cozy temps and autumn foliage take over, but there are certain summer dresses and sleeveless tops I don't feel like I've gotten enough wear out of. I was mindful to only add pieces I absolutely loved to my closet this summer, so I want be sure I'm maximizing each one.
Since I'm not ready to pack them away just yet, I've been brainstorming ways to extend the life of my summer wardrobe and have zeroed in on a few key items that can help facilitate that. From oversize sweaters paired with mini skirts to leather boots worn with dresses to tailored trousers for my crop tops, there are five items I'm eyeing to help me wear my summer wardrobe through fall. Below I'm highlighting those five, plus the styling tips I plan to use for each one.
TROUSERS
Transitional weather has met its match. Pair a chic tailored trouser with your favorite crop top or sleeveless shirt for an instant outfit ready to take on the changing seasons. Your favorite summer tops will receive a few more months of wear and you have another outfit formula to add to your arsenal. Throw a sweater over your shoulders for a foolproof in-between-seasons look.
OVERSIZE SWEATERS
Your shorts and skirts will see more life by styling them with a cozy oversize sweater. This pairing balances the cooler temps with a warmer top and allows you to continue wearing your favorite leg-bearing bottoms all season.
BOOTS
Don't put away your summer dresses just yet, simply swap your sandals for a pair of knee-high boots and suddenly the same dress is giving fall. If the temperatures are too low for the dress alone add a sweater or denim jacket to complete the look.
BLAZER
Blazers are the wardrobe gift that keeps on giving. Not only do they add polish to any outfit, but they can also be paired with virtually anything—shorts, dresses, skirts, jeans, you name it. Throw your favorite blazer over an otherwise summer outfit and you're instantly ready for fall.
LOAFERS
Much like knee-high boots, loafers are an easy shoe swap that can make linen trousers or cottagecore dresses feel fall appropriate. I especially love loafers paired with chunky ankle socks to make your outfit feel extra cozy (not to mention keep your feet warm).
Next up: I'm planning my fall wardrobe—these 5 basics will be front-runners.

-
Sorry, Crewneck Tees—in 2026, Everyone With Taste Will Be Layering Sweaters Like ThisThe recipe for a perfect winter outfit.
-
The Ashley Olsen Way to Make Simple Black Coats Look Chic, Not BoringIt's so easy, yet so impactful.
-
Looking Stylish This Fall Means Wearing Your Pretty Dresses With This Unexpected ItemHere's how to master the look.
-
Anyone Can Wear a Cardigan, But Only Fashion People Wear Them Like *This*Take note.
-
5 Street Style Trends From Milan Fashion Week That Will Be Everywhere This FallTake notes.
-
This Dated Denim Pairing Is Suddenly the Chicest Way to Wear Jeans for Fall 2025Easy and stylish.
-
Everything Who What Wear Editors Saw, Wore, Did, and Ate During NYFWLet's dive in, shall we?
-
Paris Hilton's World: Her Pink Motorola Razr, Favorite Y2K Looks, and What 11:11 Media Means to HerA glimpse into the life of this savvy entrepreneur.

