Linen Sleeveless Tee

Sleeveless tops are a warm weather staple, and when they are made from brightly colored linen, they’re quintessentially summer. But that doesn’t stop them from procuring a place among your fall favorites. Use it as an underpinning to a work-ready charcoal pinstripe suit, or pair it with an evening-ready black maxi skirt and a mix of heavy metal necklaces for an after-dark ensemble with an edge.
To buy: Madewell Overlook Linen, $42
Beaded Bangle

A metal beaded bracelet—you know, the one you haven’t taken off all summer— is one beach ready bauble that shifts seamlessly from this season to the next. After Labor Day, give this beaded beauty an autumnal upgrade by layering it alongside an elegant gold watch, or let it be the center of attention when surrounded by a wrist full of gold bangles and chain link bracelets.
To buy: Mango Contrasted Bead Bangle, $30
Black Shorts

No need to banish your little black shorts to the back of the closet once September rolls around. Work a super sharp fall look around them by pairing with a pair of short boots (an autumn essential) and a patterned button-down shirt. Swap the button-down for a slouchy cashmere sweater in a shade of camel and add black tights when it really starts to cool down.
To buy: Mango Cotton-Twill Chino, $30
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White Jeans

It’s an established fact that white can be worn long after Labor Day, and when it comes to year-round wearability, white jeans reign supreme. While they are a core piece in any summer wardrobe, they can anchor an autumnal ensemble as well. Try them with a tweed jacket, a color block tee and a low heeled pointy heel pump in red.
To buy: Mango Low-Rise Super Slim, $60
Summer Weight Scarf

That colorful cotton wrap that keeps breezes (and air conditioning) at bay can still be a go-to accessory come fall. Blue jeans, a white button-down, and ballet flats) will get an instant lift with the addition of this orange tasseled scarf, and it will also look perfectly in place with a edgy after-dark look of a sleek black jumpsuit and leather jacket.
To buy: Bungalow 8 Orange Cotton Scarf, $140
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Maxi Dress

Undeniably one of your summer wardrobe workhorses, the long tank dress can still be your go-to piece post Labor Day. While you’ll spend warm days and nights wearing it with little more than sandals and some baubles, its autumn revival requires adding a black quilted leather jacket), booties and a bold color or leopard print clutch for a street-chic evening ensemble.
To buy: Rick Owens Cotton Jersey Maxi, $275
Silk Sundress

A strappy summer frock that’s tailor-made for hot days and sultry nights can also be an October standby when paired with the right pieces. A denim jacket, motorcycle boots and leather belt lend a tough factor to this printed halter dress, not to mention making it more seasonally appropriate.
To buy: Steven Alan Fletcher Dress, $179
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Striped Long-Sleeve

This classic tee inspired by French sailors doesn’t need to be docked once the wardrobe shifts into fall. While it will top your white jeans all summer, come September you can give this top new play by wearing it over a chambray button-down shirt and pulling on a poppy red pencil skirt.
To buy: Chance Boatneck Stripe, $68
Printed Loose Fit Trouser

Summer 2012 has been all about the printed pant—especially ones with a relaxed fit and made from silky fabrics. But don’t write this style off once the mercury starts to dip. Make the pants a fall essential by wearing them with a black blazer, a slim fit cream tee and the cool wedge high top sneaker.
To buy: Ikat Print Jersey Tapered Trousers, $56
Graphic Wedge

It may be the heel of choice for summer, but the platform wedge sandal can transition easily into next season despite its skin—exposing silhouette. When the weather is pleasantly cool, pair them with a wide leg trouser (the pant shape for fall), a graphic tee and cardigan. Or, slip them on with a black tight and an of-the-moment peplum dress.
To buy: Zara Printed Platform Wedge, $90