Luxury Finds for Labor Day Weekend Looks
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Labor Day Weekend marks the unofficial end of summer—a final hurrah filled with pool parties, weekend getaways, rooftop brunches, and last-minute vacations. It’s a time to unwind, dress up, and celebrate all things sun-soaked and stylish—before fall fully sets in.
Whether you’re escaping for a coastal retreat, attending a chic backyard bash, or just soaking up the last of summer’s golden glow, your outfit should feel effortlessly elevated. And the best part? You don’t need to spend a fortune to look the part.
At High Society Resale Boutique, we’ve curated the perfect mix of luxury looks and designer finds to help you close out summer in style. Here’s your guide to building the ultimate Labor Day Weekend wardrobe from resale fashion.
1. The End-of-Summer Statement Dress
Labor Day calls for at least one jaw-dropping dress. Think flowy silhouettes, bold prints, and breathable fabrics with designer-level detailing.
Look For:
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Linen and cotton midi dresses from brands like Reformation or Zimmermann
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Vintage silk slip dresses perfect for layering or wearing solo
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Flowy maxis in boho prints or solid white for that crisp summer vibe
Styling Tip:
Pair with espadrilles and gold hoops for a complete brunch-to-beach outfit.
2. The Elevated Matching Set
Matching sets are the MVP of weekend travel. They’re comfortable, chic, and insanely easy to style. You’ll look polished with minimal effort—ideal for a packed itinerary.
Try:
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Crop top + wide-leg pants in lightweight cotton or linen
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Button-down shirt + shorts set in a monochrome palette
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Knitted sets in creamy neutrals for cooler nights
Resale Favorites:
Look out for high-end resort wear brands like FARM Rio, MISA Los Angeles, or Alice + Olivia.
3. Designer Swimwear & Cover-Ups
If your Labor Day plans involve lounging poolside or by the lake, go for designer swimwear and elevated cover-ups that double as daywear.
Shop Resale For:
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One-piece suits with cutouts or metallic detailing
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Bikini sets from designers like Mara Hoffman or Tory Burch
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Sheer maxi dresses, kimonos, or tunics as stylish cover-ups
Bonus Tip:
A neutral swimsuit under high-waisted trousers or a button-up gives you a trendy, casual look for a post-swim lunch.
4. Resort-Inspired Accessories
Accessories can make or break your weekend wardrobe. This is your moment to go bold, colorful, or ultra-luxe.
Pack These:
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Oversized sunglasses in tortoiseshell or white frames
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Beaded, woven, or raffia handbags
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Gold or shell jewelry layered over swimwear or sundresses
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Patterned scarves (wear as a head wrap, halter top, or tied to your tote)
High Society Tip:
Resale is the best way to score unique vintage accessories—our shelves are full of one-of-a-kind pieces.
5. Statement Sandals & Transitional Footwear
The weekend might call for more than one pair of shoes, so aim for versatile picks that are both comfortable and fashion-forward.
Top Picks:
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Luxe flat sandals (Hermès Oran-style or leather slides)
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Platform espadrilles or block heels
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Western-style boots for a day-to-night outfit
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Trendy sneakers for casual adventures
Smart Styling:
Stick to neutral tones if you want shoes that work across outfits. Or go bold with a pop of color and keep your outfit more muted.
6. The Transitional Layer
Even if the sun’s out, evening breezes and chilly AC mean you’ll need one good layering piece.
Go For:
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Lightweight cashmere or open-knit cardigans
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Cropped denim or bomber jackets
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A neutral blazer that dresses up even a basic outfit
Look For in Resale:
Try Theory, Vince, Free People, or designer vintage brands. These layers are practical without sacrificing style.
7. Day-to-Night Flex Pieces
Not sure what your day will hold? Go for outfits that transition seamlessly.
Examples:
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A halter maxi dress that doubles as a poolside cover-up and evening attire
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A romper or jumpsuit with a statement belt and layered jewelry
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A matching set that can be worn together or mixed into other looks
Styling Tip:
Bring one pair of bold earrings and a standout clutch to elevate any daytime outfit after sunset.
8. Weekend-Ready Designer Bags
It’s not a luxury weekend look without the bag to match. For LDW, you want something that makes a statement but is still functional.
Choose From:
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Mini crossbodies for hands-free fun
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Tote bags in straw, canvas, or leather for beach and brunch
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Bold-colored bags to pop against a neutral outfit
Hot in Resale:
We often carry designer bags from Chanel, Louis Vuitton, Gucci, and Saint Laurent at a fraction of retail price.
9. Final Touches: Sunglasses, Scarves & Jewelry
Elevated basics are made better with accessories. Don’t overpack—just focus on impactful, versatile pieces.
Pack These:
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One pair of gold hoops
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One silk scarf
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Two pairs of sunglasses (bold + neutral)
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A layered necklace set
These items take up little space in your weekender bag but will upgrade every look.
What’s Trending This LDW?
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All white everything – a Labor Day classic
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Straw bags with bold detailing
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Light, sheer fabrics layered over swimsuits
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Mixing textures—linen with leather, cotton with satin
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Subtle Americana vibes—navy, red accents, gold jewelry
All of these pieces can be found in our curated High Society racks—and many are one-of-a-kind.
Why Shop Resale for LDW?
Labor Day fashion doesn’t have to mean fast fashion or big-box sales. When you shop resale:
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You get luxury for less
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You find unique pieces no one else has
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You support sustainability
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You can often earn store credit by consigning what you no longer wear
We’re here to help you build a holiday look that feels high-end without the high price tag.
Final Thoughts: Leave Summer in Style
Labor Day Weekend is your last big summer fashion moment—so make it count. With the right mix of statement pieces, transitional staples, and standout accessories, you can put together looks that turn heads from Friday through Monday.
At High Society Resale Boutique, our team is ready to help you build the perfect LDW wardrobe. Come browse our best pre-fall dresses, resortwear finds, and designer bags before they’re gone.
Celebrate summer. Dress the part. Shop resale.