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Summer-to-fall transition outfits

When the air turns crisp and the leaves begin to fall, it’s clear the holidays are approaching. It’s one reason why fall is so many people’s favorite season, but that chill in the air also means you will need to make some changes to your wardrobe.

So, say goodbye to your flip-flops and bathing suits in exchange for hats and scarves instead, and consider pushing your tank tops and shorts to the back of your drawer to make room for sweaters and boots. Below, we’ve rounded up some essentials that are sure to become your go-to pieces for fall.

In this article: Levi’s Trucker Jacket, Lucky Brand Basel Ankle Booties and Lands’ End Long-Sleeve Open Long Cardigan Sweater

The best summer-to-fall outfits for men

PJ Paul Jones Men's Lightweight Sport Coat

PJ Paul Jones Men’s Lightweight Sport Coat

Take your wardrobe up a notch with a classic blazer. The light fabric is breathable when it’s warm out while cutting the chill in the cold. This blazer has all of the details you crave with real front pockets, notched lapel, one-button closure and a left chest pocket.

Amazon Essentials Men's V-Neck Cotton Knitted Cardigan Sweater

Amazon Essentials Men’s V-Neck Cotton Knitted Cardigan Sweater

If a zip-up hoodie is your staple for brisk autumn days, it might be time to upgrade with a cardigan. This sweater is ultra-comfortable, machine washable and has two pockets for everything you need so that the old hoodie can stay at home.

Levi's Trucker Jacket

Levi’s Trucker Jacket

No fall-to-summer outfit is complete without a denim jacket, and this well-made classic will last a lifetime. Available in a dozen colors, this jacket has a timeless but rugged style and features four pockets for your essentials.

Levi's Men's 514 Straight Fit Jeans

Levi’s Men’s 514 Straight Fit Jeans

Once you find your favorite pair of jeans, you want to wear them all of the time, so finding ones that work for summer-to-fall outfits is a must. Dark indigo with a minimal fade, these straight-fit jeans are a versatile staple crafted from high-quality denim that will last multiple seasons.

Comfort Colors Adult Heavyweight Short-Sleeve Tee

Comfort Colors Adult Heavyweight Short-Sleeve Tee

No one can have too many T-shirts. This one is soft, thick and made to last. It comes in more than two dozen colors, so you can have a rainbow of them in your wardrobe.

The best summer to fall outfits for women

Lucky Brand Basel Ankle Booties

Lucky Brand Basel Ankle Booties

This everyday bootie perfectly transitions from summer dresses to fall flannels. Made with 100% leather and a side zip so you can easily pull them on and off, this 1.5-inch heel bootie is available in a dozen colors.

Lands' End Long-Sleeve Open Long Cardigan Sweater

Lands’ End Long-Sleeve Open Long Cardigan Sweater

Whether the AC is bumping in the office or your maxi dress needs an extra layer, this versatile 100% cotton cardigan is what you need for comfort and warmth. Plus, the two roomy pockets are perfect for carrying glasses, keys or a phone.

Women's Levi's Boyfriend Jeans

Women’s Levi’s Boyfriend Jeans

We just can’t seem to get enough of the boyfriend jean because of its cute, casual and comfortable style. These have the perfect mix of stretch and cotton for a loose but tailored fit.

Levi's Women's Vintage Overalls

Levi’s Women’s Vintage Overalls

Stay adorable in a summer-to-fall outfit that doesn’t need much else to make it a complete look. The adjustable straps, patch pocket detail and side button closure make these overalls easy to wear with whatever you prefer.

Madewell Northside Vintage Tee Pack

Madewell Northside Vintage Tee Pack

Keep it classic with these perfectly soft T-shirts made from 100% cotton. This stylish three-pack comes with shirts in white, black and navy blue, so they go with everything.

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