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Sure, summer is ending, but the celebrations aren’t over just yet. Send off the warm-weather season in style by stepping into these fashionable Labor Day outfit ideas. Whether your plans include hanging poolside or hosting a party, the three-day weekend provides ample opportunity to say goodbye to summer essentials and move toward fresh fall finds.
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This Labor Day weekend, wave goodbye to your white linen looks and gravitate toward more transitional pieces. With fashion experts predicting bomber jackets, leather and button-downs all be foolproof trends this fall, it’s an excellent time to invest in one or all of the above. At the very least, reach for something neon green or camel: Both colors will also be huge come fall.
What to wear this Labor Day?
You can start small by layering your beloved summer styles with a fall-approved blazer; or go all-out with three new Labor Day outfit ideas; there’s no wrong way to go here and we’ll prove it. We’ve found seven transitional Labor Day outfit ideas that’ll work from this season to the next.
1. Start with Girlfriend Collective’s sustainable romper
Set Labor Day weekend off on the right note by streamlining your outfit by starting with Girlfriend Collective’s Stretch Woven Romper. Available in three colors, including dark olive, Varsity blue and black, and created in women’s extended sizes ranging from XXS to 6X. Crafted from 86% recycled water bottles and 14% spandex, the drawstring waist and water-resistant fabric provide a comfortable-yet-chic silhouette that’s suitable anytime, anywhere.
Layer your look by adding this best-selling blazer from Amazon. It’s available in women’s sizes small to XXL, two silhouettes (long sleeve or sleeves), as well as 30 different ready-to-wear colors. Shoppers can choose to go for a monochromatic look or opt for something a bit bolder. Either way, reviewers love how the oversized silhouette runs “true to size” and claim it’s the first blazer “they’ve really loved to wear.”
Rely on standout accessories like Artizan’s layered necklace set to take your look to the next level. Between the mixed silver-and-18k-gold chains, evil eye pendant and three layers, who could even resist this piece? No one, especially when adding a bold headband like this. Featuring five headbands, all in different colors, this fan-favorite is beloved for being “comfy and stylish.”
Speaking of style, round out your look with Coconut Gaucho’s two-toned cowboy boots, available in women’s shoe sizes 5 to 12. All three colors feature the same Western-inspired stitching, predicted to be one of fall’s most sought-after styles, plus a 1½-inch block heel that’ll add the right amount of height to any frame.
2. Elevate Intimissimi’s cashmere top with Larroude’s ultra-chic clogs
A good Labor Day outfit idea doesn’t have to be something over-the-top. Don’t believe us? Try this Intimissimi’s boat-neck top. Available in women’s sizes S to XL, the boat-neck silhouette comes in seven shades, all of which feature the same cashmere material. Perfect for transitioning from summer to fall, it’s important to note that while the cashmere material is “heavier” than cotton or linen, it’s on the sheerer side; for a more covered approach you’ll want to layer it with this silk bralette.
Match this classic top with a pair of denim you’ll wear on repeat—and we highly recommend Frame’s Le Original denim. The cult-favorite selection is vintage-inspired, with a slim, straight leg, high-rise waist that cinches for a curve-enhancing profile. Available in sizes 23 to 34, this piece is ready to wear in four washes, with Sunkissed’s broken-in, distressed wash earning our praise.
Elevate this ensemble by stepping into Larroude’s Miso Clogs. Available in women’s shoe sizes 5 to 10, shoppers can pick from caramel, caramel plaid, green tartan and ivory. Each design features the same effortless appeal, heightened with a 3.6-inch block heel and vintage look.
To avoid looking “too dressed down,” dress effortlessly elevate it with Rare Beauty’s Lip Soufflé Matte Cream Lipstick in our favorite shade, Brave, a muted terracotta. The soft velvety matte lip cream is weightless and adds a rich orange-brown hue that provides hydration to your lips while making a stylish statement.
3. Take Rifle Paper Co.’s swimsuit from day-to-night thanks to J.Crew’s button-down shirt
Yes, summer is winding down, but searching for the best places to buy swimsuits is a year-round task. Naturally, that’s why this one-piece from Rifle Paper Co.’s new drop is a worthwhile investment to make this Labor Day and beyond. Available in women’s extended sizes 2 to 22, there’s the Lea print (a greenish hue) and Garden Party Rust (a burnt orange-red combination), which are up for grabs. Both versions showcase the same deep V-neck front and back and ruffle detailing on the shoulder straps. What we love most is the compression material it’s made from. It sucks your body in in all the right places while providing ample coverage. Plus, the silhouette is endlessly versatile.
Seamlessly transition this swimsuit from day to night with Levi’s denim shorts. Ready to wear in women’s plus sizes 14 to 26, the vintage-inspired fit offers an easy-to-wear, relaxed silhouette and effortlessly flattering high-waist. These shorts are even more fashionable when opting for a button-up shirt like this one from Summersalt.
Soft and sustainable, this button-up shirt is available in women’s regular and extended sizes, ranging from small to 2X and in two shades: white and the blue-and-white Cabana Stripe in the Sky. Designed with a high-low hem and showcasing an oversized fit, the wrinkle-resistant piece is wearable on its own or when going from the pool to the party.
While a traditional flat sandal can and will work with this outfit, we recommend adding a heel for extra versatility. The Arianna high heel sandal from Lulus is a great option. Available in women’s shoe styles 5 to 11, the soft vegan suede shoe is featured in two colors—camel and white—and elevated with a slender toe strap made of clear vinyl and topped off with a 3.75-inch block heel.
4. Channel your inner schoolgirl with Reformation’s mini dress
School’s back in session in more than one way with Reformation’s Hackney Dress. Available in women’s sizes XS to XL, there are three different houndstooth patterns up for grabs, with each as fantastic as the last. The loose-fitting mini dress has a timeless square neck, wide straps for extra coverage and an accessible back zipper.
With TikTok declaring everything old is new again, the ’90s are back and hotter than ever—these Steve Madden Kimberley Platform Heel Loafers included. Available in women’s shoe sizes 5 to 11, these near-perfectly reviewed loafers are on the top of many lists. One reviewer called them “the most comfortable pair of loafers,” while another shopper claims “they were wearable for long periods,” a pleasant surprise considering their 4.5-inch lug sole platform.
Swing a statement purse like Coach’s Swinger bag over your shoulder. Part of The Coach Originals from the ’80s features the same streamlined glove-tanned leather style, iconic turn-lock closure and zip-top that made this brand so legendary. In the brass/black and brass/chalk white, both versions receive a near-perfectly reviewed rating among reviewers and have an adjustable long and short strap for added versatility.
5. Add adaptability with SKIMS’ bodysuit and a two-piece matching set from Adidas
This SKIMS Fits Everybody bodysuit will build the perfect base no matter what. It’s available in women’s extended sizes, ranging from XXS to 4X, and the square neckline and scoop back are flattering on every single body type. Plus, the 13 shades include neutrals as well as bold colors like Mykonos blue. This flattering one-piece can be dressed up or dressed down.
Find a middle ground by reaching for these high-rise cotton shorts from Adidas. The Original Boxing Shorts offers comfort and chic and are available in women’s women’s regular sizes and extended sizes from 1X to 4X. The baby blue base and white stitching ring true to the classic Adidas brand, while the colorful embroidery adds a pop of color.
If or when temperatures begin to dip, stay prepared by having this matching Original Blazer in your arsenal. Ready to wear in women’s regular and extended sizing from 1X to 4 and features a button closure and side slits while elevating the pale Almost Blue hue with a graphic text design on the back.
Add contrast to your look via these Adidas Forum Bonega Platform sneakers. Available in women’s sizes 5 to 11, reviewers love all three color combinations up for grabs, but the Cloud White/Cloud White/Gold Metallic is our top pick. These sneakers earned a perfect five-star rating among shoppers, with one reviewer loving how “comfortable the platform was” and another shopper adding that this color combination added a “vintage feel” to their look.
Glam things up by swiping on a coat (or two) of Huda Beauty’s Power Bullet Matte Lipstick in Masquerade. The highly-pigmented aubergine shade is cool toned and will flatter all skin types while providing unparalleled color in a silky-smooth formula. Last but not least, reach for this 18k gold hoop set that features eight different styles.
6. Show your spirit in Amanda Uprichard’s matching set and Show Me Your Mumu’s flag sweater
Turn heads this Labor Day in Amanda Uprichard’s Laurena Set. Available in women’s sizes XS to L, this matching halter-neck top and high-rise mini skirt are designed in piece-patched denim fabric. Reminiscent of the iconic Britney Spears and Justin Timberlake look from the 2001 AMAs, this modernized version has earned TikTok sensation Tinx’s approval; she shared on Instagram just how much she loved this set earlier this month.
While any sandal or heel would look superb with this set, to make this Labor Day outfit idea transitional, the Vince Camuto Glissonda boot has our vote. Crafted from burnished suede, the slouchy pointed-toe boot offers the same lusted-after Western-style topstitching, but the taller silhouette provides endless versatility come the colder months.
Speaking of colder weather—come nightfall, stay warm and show your patriotic spirit by layering on this Fireside Sweater. Between the oversized fit, knitted American flag and ribbed detailing throughout were confident this piece will become a year-round staple.
7. Stay stylish in Saylor’s sparkly top and pair it with Amazon’s glittery bag
Holidays are meant for statement outfits, so why not step into Saylor NYC’s Kamara Top and make a stylish one. Suitable for day or night wear, this rainbow metallic top has all the bells and whistles, ranging from a tie front to peplum sleeves and even puffed shoulders. Which, of course, when looking to take an outfit and make it a look, this piece ranks high on your list.
With so much going on on top, we recommend stepping into a relaxed denim option like these jeans. Laidback and lightweight, the JEN7 BY 7 FOR ALL MANKIND raw hem ankle straight leg jeans are available in sizes 0 to 18 and two different colors, including a dark Destiny Fall color and a lighter wash named Malaga. Both washes offer a straight-leg bottom and comfortable enhanceME shaping panels that subtly slim and sculpt your curves.
Accessorize appropriately with this silver glitter purse from Amazon. According to reviewers, not only is it the “perfect Cult Gaia dupe,” but the adjustable straps make it endlessly versatile; remove the straps and use them as a clutch for your next wedding or add them for everyday use.
Finish the look for these affordable best-selling high-heeled sandals from Amazon. With more than 5,200 reviewers singing their praises, there are 22 different textures and colors to choose. According to shoppers, each option is as “comfortable to wear” as the last and “ideal for every occasion.”
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Prices were accurate at the time this article was published but may change over time.
