In my opinion, the transition from summer to fall is the trickiest time of year. Once the end of August hits, I’m always ready to break out my cold-weather pieces, but the sweltering heat usually stops me in my tracks. This year, I enlisted the help of New York–based Who What Wear editor Grace O’Connell-Joshua to show me the outfits she’s wearing that blend her summery items with pieces that feel more in line with fall. To transition her looks, she’s combining summer trends like crochet tops and ribbed midi dresses with fall-forward silhouettes like leather jackets and suede booties. And she’s finding all of these pieces at The Style Room, a microsite powered by Zappos that’s loaded with versatile pieces, must-have basics, and a healthy dose of outfit inspiration. Not only does the site offer up seasonal trends and closet staples, but it’s a great place to turn to if you’re looking for ways to remix your current wardrobe. In need of some inspiration? Keep scrolling for three elevated, on-trend outfits that you’ll want to re-create immediately.
“This look is basically my summer-to-fall uniform. What can I say? I love a great white tank top. It’s the ultimate basic and can be styled in an almost infinite amount of ways. In this instance, I chose these low-rise trousers, an oversize tote that’s perfect for the office, and chunky loafers that feel very fall-forward. (Editor tip: A good pair of loafers is perfect when you need a flat shoe that looks sophisticated and stylish.) And for chillier days, I could easily layer a cool jacket or cardigan over the tank.” — Grace O’Connell-Joshua, assistant shopping editor
“If there’s one thing I look forward to every fall, it’s getting to wear a great pair of boots and finally pulling out a good leather jacket. These two pieces are essentials for the season, and you can style them on repeat. Since we’re not exactly in fall yet, I styled these chic suede Stuart Weitzman boots with a dress to keep things a little summery. The earthy green color of this See by Chloé bag is the perfect summer-to-fall shade. I have a feeling I’ll be wearing this bag all the time.” — O’Connell-Joshua
“When I first tried on this Line and Dot crochet top, I was in love. I’m a huge fan of crochet for summer, but styling it with these Paige jeans and brown leather accessories gives this look a pre-fall feeling. I layered it over a Free People bralette. (I recommend that everyone own one.) When it comes to denim, I always gravitate toward Paige jeans. They’re so soft and flattering. This is the perfect look for running around the city and grabbing lunch with friends. It’s stylish but easy to wear.” — O’Connell-Joshua
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