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In the thick of high summer, there are two questions that present themselves year after year: What to wear when it’s swelteringly hot, and how does one even begin to start thinking about a fall wardrobe? Whether you’re embracing a maxi dress summer uniform or leaning into mesh ballet flats, there are a handful of tried-and-true tricks for approaching the aforementioned questions. And still, when it comes to dressing in-between seasons, there’s one style solution that is sure to stand the test of time: vintage.
Take Phoebe Philo’s spring 2016 Celine collection, for example. The first six looks in the show were different renditions of black and white lace silk dresses and camisoles, each of which has become an in-demand style across resale sites since their debut. As highly-sought after pieces, they have claimed their place in the “if you know, you know” collection of secondhand pieces that will, simply put, always be good. Alexander McQueen’s spring 2017 collection also holds a spot as a set of designs that have an everlasting effect on shoppers (the empire waistlines, handkerchief-point skirts, and knit dresses are each worthy of a saved search on The RealReal). In other words, when in doubt, go with the best in show—the ensembles that have already proved a certain staying power season after season.
Below is an edit of that very genre. From Prada bags of the 1990s to a Versace mini dress of the 2000s, this collection of pieces covers trends of decades past that still manage to hold relevance. There are also more recent pieces, such as a floral tent dress from Chopova Lowena’s spring 2023 collection, red patent Carel Mary Janes, and a pair of silver Wales Bonner Adidas, that show early signs as high-appreciating assets. In other words, you might want to act fast, because they are sure to sell soon.
In addition to Phoebe Philo’s inimitable lace number for Celine, a pair of patent red Carel Mary Jane shoes is a wise investment that can be styled season after season. Wear them with Sophie Buhai’s sterling silver Egg Hoop Earrings and Prada’s Vitello-Trimmed Tessuto Moon Bag — a twist on the classic nylon bag from the Italian fashion house. Chopova Lowena’s floral tent dress is a no-brainer for summer-to-fall dressing, especially when paired with Miu Miu’s black ballet flats and Calvin Klein’s mini alligator-embossed chocolate leather bag. Top off the outfit with a piece of statement jewelry, such as Paco Rabanne’s brass chain-link bracelet.
Khaite’s cotton square-neck, empire-waist dress, although only several seasons old, has already become an in-demand summer essential on resale sites. And layered over a long-sleeve t-shirt or underneath a leather jacket, it can easily function as a fall necessity, too. Wear it with Hereu’s brown leather fisherman sandals and Jacquemus’ go-over-anything knit cardigan. Add a hint of color to the look with one of Marni’s beloved market totes—this floral iteration is an especially rare find. If you prefer to dive even deeper into the vintage vault, perhaps Jean Paul Gaultier’s mesh dress from spring/summer 2004 (found in Vestiaire Collective’s Archive Room) is more your speed. Dress it up by way of silver with Prada’s patent leather silver slingbacks and Frank Gehry’s wavy Tiffany cuff. To ground the look in something truly everlasting, carry YSL’s Le 5 à 7 in black, a bag that will never grow old.
Here’s a look you’ll want to wear every day: Khaite’s Ian jeans are perhaps the most popular jeans on the market right now, so these are sure to fly fast (hot tip, setting an alert for Khaite jeans on secondhand sites is an easy win). Wear them with a pair of chunky platform loafers, such as the brown leather pair from Celine, and if you prefer to continue in that direction, Celine’s brown leather 4-pocket jacket (from the 1990s!) is another piece that will continue to hold its value over time. Add a hint of shine to the look with Of Rare Origin’s pearl drop earrings. If you’re hunting for something more bohemian, Alexander McQueen’s 2017 knitted long evening dress (this one’s from the runway) is just the trick. Pair it with platform Mary Jane shoes such as Nodaleto’s, a pair of iconic Celine sunglasses, and a Fendi baguette.
While summer is high time for a mini dress moment, one could argue that you can easily style a mini into fall. Versace’s 2009 runway mini dress, which reveals the same corset-esque silhouettes we’re seeing on runways today, is a perfect mini. Wear it with a pair of metallic Prada platforms and matching Chanel stud earrings. For a real throwback, finish the look with Louis Vuitton’s Eva Clutch. And finally, dress down for those slower in-between season days with a pair of Wales Bonner Adidas (this silver pair is from the latest drop), Issey Miyake pleated pants, a Gucci shoulder bag you’ll love for life, and of course, a Bode patchwork number.
Previous monthly arrivals, below