Summer is my favorite season to shop for. I love the versatility, romanticism, and ease that summer clothing offers—the light raw silks, sheer cottons, sequined miniskirts, and feminine details. The irony, however, is that I live in New England, which means I only get to wear my summer wardrobe for about two months until the temperatures dip and the Barbour coats come out. But cold weather be damned! This year, I refuse to swap my sheer midis and lace slip skirts for fleece-lined leggings and heavy wool trousers that don’t spark joy.
So, I developed four styling tips to extend the seasonal shelf life of my summer wardrobe, especially my favorite lightweight skirts and shorts. Because when you love your summer wardrobe as much as I do, it’s worth finding ways to wear it year-round. And trust me: By building outfits with clothes you already own and challenging yourself not to rely on new-in trends, you’ll also better understand your personal style. And isn't that always the goal when getting dressed?
Ahead, here’s how I'm styling my favorite warm-weather items to withstand New England fall and winter.
Strategic Layering
First up is smart layering—think a gauzy tulle or chiffon skirt with a thick ribbed cashmere turtleneck from The Row or a cropped cable-knit sweater from Khaite. Add structure with an oversized wool coat, like a clean-lined version from Totême or Max Mara’s classic wrap. Then finish with tall leather boots or sleek ankle boots to anchor the look.
Summer Shimmer in Winter
No matter the season, I can’t resist the allure of a shimmering sequin skirt. To winter-proof the bold, eye-catching bottom, I layer it over straight-leg jeans and top it with a soft J.Crew sweater. The look is relaxed but fun—just how I like it.
Sheers and Lace
The same layering philosophy applies to styling summery sheers and lace elements. Try pairing a see-through midi skirt or your favorite slip dress with a loose, oversized cashmere crewneck and Manolo Blahnik pumps for a night out that feels light yet winter-ready. It’s soft against sharp, a contrast between sensuality and structure.
Summer Shorts
Finally, even summery shorts can have a winter moment with the right pieces to prop them up. My personal favorite is pairing lace-trimmed shorts with a similar-toned wool sweater and a leather trench. It says, I know winter is coming, but these legs aren’t giving up summer just yet.
