Figuring out what to wear for your Labor Day weekend plans can take a bit more thought than the rest of your summer and early fall outfits—but we welcome the challenge. On one hand, this pool party-filled weekend is traditionally the last hurrah of summer, which may inspire you to bring out the season’s top trends and silhouettes. On the other hand, however, it can be a key time to introduce cool-weather pieces in preparation for breezier autumn weather. From laid-back Bermuda shorts to classic asymmetrical tops and dark-wash denim, there’s lots of range to explore in this time of transitional dressing. Searching high and low for the ideal ensemble to give summer a proper send-off? Ahead, we’ve rounded up nine Labor Day outfit ideas to fit every occasion, activity, and personal style aesthetic, complete with on-trend product picks.
High Volume
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Don’t reserve this summer’s nostalgic bubble silhouette for only the warmest months. Try transitioning a voluminous, puffed design—namely, this trend-forward top—by pairing it with a very demure maxi skirt in a similar fabric. While we believe in wearing whites any time of year you want, Labor Day weekend is a great time to get some additional mileage out of your breeziest summer palettes.
Bold Belt
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Strike a balance during your poolside plans with a low-lift, high-impact ensemble. Here, model Paloma Elsesser demonstrates how to expertly layer cool-girl staples—including a boho chic wide belt and semi-sheer swim coverup—for an outfit that takes you from the beach chair to drinks or shopping.
Lightweight Linen
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Planning for a more elegant occasion, such as a rooftop dinner party? Take inspiration from Kelly Rutherford’s bespoke elevator selfies by choosing a coordinating linen set. Delicate floral cutouts are the trés chic icing on top of the proverbial cake.
Breezy Basics
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During sweltering weather, we’re constantly toeing the line between practical basics and something more dressed-up—and this look strikes that essential balance. To take loose-fitting Bermuda shorts and a button-down to the next level, try styling them with a thick stack of silver jewelry and resort-ready accessories.
Bordeaux Beauty
@sofiagrainge / Instagram
This fall, we’re expecting to see moody shades of bordeaux, wine, and oxblood across our social feeds—and when has Sofia Richie-Grainge ever steered us wrong? We’d plan pairing this deep red handbag with a sophisticated, asymmetrical top and high-contrast belt.
Demure Denim
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Minimalist, ‘90s-inspired designs remain reliably timeless, and this dark-wash denim seamlessly fits the assignment. Pair this ensemble with some pointed-toe kitten heels to bring the nostalgic look together.
Relaxed Neutrals
@jilla.tequila / Instagram
Looking forward to soaking up a little bit of well-deserved leisure time (read: browsing online sales) this long weekend? For a look that’s still comfy but feels slightly inspired, save your go-to sweatpants set for another day. Instead, we’d recommend soft knit fabrics to keep things comfy, while a Brat green handbag feels impossibly fresh.
Wild Side
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As the temperatures begin to dip, we can’t help but look forward to pulling our cold-weather essentials from the back of our closets. A slightly faded pair of leopard print pants and a semi-sheer top make fall favorites appropriate for Labor Day weekend weather.
Color Coordination
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This year’s hottest color trends have spanned from acidic shades of lime green to buttery yellows and soft periwinkles. Consider this holiday weekend as an opportunity to further play with the season’s most vibrant palettes, combined with a trusted pair of white pants and dainty jewelry.