As fall’s cooler temps finally roll in, it’s time to pack away some of the easy breezy fashion staples that got us through a brutally hot summer. Flip flops will be traded out for a pair of comfy, chunky boots, and we’ll bid adieu to our beloved wide-leg linen pants in favor of cozy leggings. Some pieces, though, will help you through the seasonal switchover, like that can’t-live-without white button-up shirt, aka the perfect piece to transition your wardrobe into fall.

If you’re hoping to keep your casual-chic summer aesthetic going for a few more weeks, AYR's Deep End Oxford, $135, will keep things fresh while bridging your wardrobe into those layering days (and yes, it’s totally OK to wear white after Labor Day!). But if you’re ready to jump right into those fall vibes, Jenni Kayne’s O’Keeffe overshirt, $225, is worth the splurge: It’s not just a comfy button-up; it can pull double duty as a light, transitional fall overshirt.

Cindy Conroy is a New York- and Toronto-based fashion expert and TV host who has worked with celebs like Christina Milian, and her work has appeared in New York Magazine and WWD, as well as PureWow.

We know about pairing a French tuck or a front tie with some wide-leg denim or even athleisure. But if you’re ready to take your summer button-up styling to the next level, Conroy says the otherwise unassuming piece can make quite a statement.

When it comes to a beloved oversized button-up, Conroy says adding a few feminine elements can get you from summertime beach living back to weekend brunches in the city.  “Style your oversized button down with glamorous drop earrings, pop your

collar and add denim for a look that is anything but boring.” She also suggests tucking it into a high-waist miniskirt, or pairing a classic white poplin with a silk hair scarf and a wide leg trouser for an “air of liberated fun.”

Some of Conroy’s favorites for the season include more classic silhouettes, such as Ralph Lauren’s Relaxed Fit Striped Cotton shirt ($148), as well as this Nic+Zoe Eyelet Sleeve Button-Up ($168; $101), which she says is still “classic, but oodles of fun.”

Yes. “A button-up isn’t actually the same thing as a button-down shirt,” Conroy says. “Button-down shirts are just plain extra. They are like button-up shirts’ sister shirt, but with extra buttons to secure the collar. This keeps your collar from moving out of place and looking like a hot mess.” These are most often seen in menswear and are typically worn for a more polished look when not wearing a tie.

“If it doesn’t have those extra buttons, it is simply a button-up shirt,” Conroy adds.

We tapped some PureWow staffer picks, paid close attention to what reviewers had to say and spoke to an insightful stylist for some inspired advice on finding the very best button-up shirts to take you into fall.

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