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No matter the weather, these summer-to-fall outfits will have you looking great

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. 

How to prepare for the transition from summer to fall

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.

However, you don’t have to shop for one season or the other. No matter what your style, there are some great shirts, pants and shoes that will work in either season and save you the trouble of having to update your wardrobe when it starts to get a little cooler out. 

The best summer to fall outfits for men

Tasso Elba Men's 2-Button Blazer

Take your wardrobe up a notch with a linen blazer that seamlessly transitions into the ultimate summer to fall outfit for work. The light fabric is breathable in the warm weather while cutting the chill in the cold. This blazer has all of the details you crave with front patch pockets, notched lapel, two-button closure and a left chest pocket.

Sold by Macy’s

Levi's Men's Sweater Knit Fleece Cardigan

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

Sold by Amazon

Polo Ralph Lauren Men's Denim Trucker Jacket

No fall-to-summer outfit is complete without a denim jacket, and this well-made classic will last a lifetime. This jacket is a timeless but rugged style with adjustable button tabs, button placket, barrel cuffs and point collar. With four pockets total, this jacket has everything you need.

Sold by Macy’s

Micheal Kors Parker Slim-Fit Selvedge 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 navy with a minimal fade, these slim-cut jeans are a versatile staple crafted from high-quality selvage denim that will last multiple seasons.

Sold by Amazon

The best summer to fall outfits for women

Code West Post It Women's Booties

This every day, every season bootie perfectly transitions from summer dresses to fall flannels and puts the old motto of “no white after labor day” to shame. Made with vegan leather and a back zip so you can easily pull on and off, this 2-inch heel bootie is easy to keep bright white since you can simply wipe them clean.

Sold by Macy’s

Tory Burch Simone Cardigan

Whether the AC is bumping in the office during the summer or your maxi dress needs an extra layer in the fall, this gorgeous 100% merino wool cardigan is the optime of comfort and warmth. The peachy coral color paired with the gold signature TB logo buttons turn a simple cardigan into a multi-seasonal staple.

Sold by Tory Burch

Women's Levi's Boyfriend Jeans

We just can't seem to get enough of the boyfriend jean because of their cute, casual and comfortable style. These basics can be paired with a simple white tee and sandals in July and worn with a cozy chunky knit sweater in October. The perfect mix of stretch and cotton for a loose but tailored fit comes in a deep blue, so it will always be in season.

Sold by Amazon and Kohls

Lucky Brand Women's Denim Boyfriend Overall Jumpsuit

Stay adorable in a summer-to-fall outfit that doesn't need much else to make it a complete look. Toss these cotton overalls over your swimsuit for a beach day, or pair them with a hoodie for an autumn vibe. The adjustable straps, patch pocket detail and side button closure make these overalls easy to wear with whatever you prefer.

Sold by Amazon and Macy’s

Hue WearEver U R The Curbside Relaxed Fit Joggers

Whether you're working from home, heading to the gym or off to run errands, these soft, light and stretchy joggers are a wardrobe must-have when picking items that will meet your needs in the summer or fall. Light enough to be breathable in the warm weather but with full coverage to handle a brisk autumn afternoon.

Sold by Amazon and Macy’s

Free People WFH Sweater Tee

Nothing quite says summer to fall outfit like a sweater t-shirt. This top is constructed with mid-weight jersey fabric and has a ribbed trim and inverted seams. The slouchy style cut with a drop shoulder and elongated sleeves would be perfect with your favorite denim shorts or boyfriend jeans.

Sold by Revolve

Cotton Citizen Classic V Neck Tee

Keep it classic with the perfect white t-shirt made from 50% Supima cotton and 50% micro-modal jersey cotton. This white t-shirt can be the ideal counterpart to all of your favorite colors, prints and textures from the summer to the fall.

Sold by Revolve


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Ryan Dempsey writes for BestReviews. BestReviews has helped millions of consumers simplify their purchasing decisions, saving them time and money.

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