Consider These 24 Dress-Outfit Ideas Your End-of-Summer Bucket List

A dear friend once told me, “We all know you live for peak summertime dressing,” and honestly, she was right. Don’t get me wrong—I’m excited to start adopting fall’s biggest trends, but practicing a socially distanced summer has left me with a bit of FOMO. To be clear: I'm missing the times of pre-COVID-19 (we know we're not going to go back to that for a while) when I could frolic about somewhere in the sun in a hot little ensemble without any worries. 

But if this time has taught me anything it’s about finding joy even in the bleakest of circumstances—and if that means throwing on a little sundress, so be it. So ahead, we’ve rounded up 24 dress outfit ideas from readers to replicate before the end of the summer—because who said you can’t wear a full look at home? Or to a picnic? You can still make the most of this summer, and find a little joy in the process, all you have to do is keep reading…

WHO: Naomi Parris 

WHAT: Tibi Two-Tone Paneled Cotton-Poplin Dress ($180); Nn Kaylah Red Mules ($150), and Cleo Nicci Sunglasses

WEAR: Unique button-up dress. 

If you’re looking for a dress outfit idea that can transition into the fall or any season for that matter; investing in a button-up dress. This piece can not only transition well, but it’s a classic outfit idea; and if you get one with special details, its sure to be anything but basic. 

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J.ING Corset Vest Shirt Dress

WHO: Caroline Lin

WHAT: Dolls Kill Black Dress; & Other Stories Chunky Layed Open Hoop Earrings ($19)

WEAR: Black spaghetti strap midi dress. 

If you’re over wearing sweatpants around the house, another alternative is opting for a house dress. But you don’t have to over-do it; opting for a simple spaghetti strap black dress is an outfit idea that’s almost as comfortable as your sweats, and still chic enough to feel like you’ve put in some effort.

WHO: Charlotte Kuhrt  

WHAT: Zalando dress and Zara sandals

WEAR: Utilitarian wrap dress. 

We may have not had far-off adventures this summer, but that doesn’t mean we can’t dress as we did. In fact, per our spring/ summer trend guide, polished utilitarian pieces that make you feel as if you’re exploring a far-off place are the trend of the season. Just plop on your utilitarian dress, log onto Window Swap, and violà your wanderlust is slightly quelled!

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Dl1961 Fire Island Utility Dress

WHO: Emma Honohan Jones

WHAT: Who What Wear Bell Short Sleeve Dress ($26); Amazon Chunky Golden Hoops ($14); Forever 21 Satin Scrunchie Set ($8) 

WEAR: Polka-dot midi dress. 

Ok, maybe this outfit idea is a little bit of a biased pick—not just because reader Emma Honohan Jones makes our Who What Wear collection dress look so good. But, I’m very much a fan of a picnic outfit idea; and since this story is a bucket list for outfit ideas, add it to your to-do list to wear a polka-dot dress to the park before fall.

WHO: Lydia 

WHAT: L'Academie Maxi Dress ($149); Jacquemus Le petit Baci ($240)

WEAR: Linen maxi dress. 

There are some summer dress outfit ideas that work year after year; this idea is just that. A linen maxi dress is a must-have in any summer capsule wardrobe because it’s not only easy to style, and lightweight, but it can be worn for seasons to come. Talk about a good investment. 

WHO: Daphne Blunt 

WHAT: Sabo Skirt Dress; Aritzia Plunge Front Cardigan ($138); vintage shoes

WEAR: Spaghetti strap minidress and a cardigan. 

The end of summer beacons in chiller breezes, and there’s no better way to get a few more wears out of your go-to spaghetti strap dress than pairing it with a cardigan. Not only is this a practical outfit idea, but as sweater sets and cardigans have been an editor favorite all summer this is a style that’s easy to adapt to any wardrobe.

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Urban Outfitters Gingham Mini Dress

WHO: Sarah Lou

WHAT: Reserved crochet dress; Becksöndergaard bag

WEAR: Crochet midi dress and ’90s-inspired shoulder bag

Summer never really feels complete if you haven’t had a day by the water—whether you choose to do a socially-distanced day at the beach or lake, or plop into the pool there’s no better end-of-summer, by the water look than a crochet-knit dress. It’s perfect to throw over your favorite swimsuit, or just wear really anywhere.

WHO: Tania Anthony 

WHAT: Verge Girl Mesh Mini Dress ($53); ASOS Powder Blue Dad Suit Blazer ($92); Zara Thin Strappy Sandals ($50) 

WEAR: Blazer, ruched minidress, and sandals. 

Getting the most out of your wardrobe is always the goal, and there’s no better way to get more use out of that slip dress in your dresser than pairing it with sandals and an oversized blazer—bonus points if you make your outfit idea monochrome like reader Tania Anthony.

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Superdown Beverly Cami Dress in White

WHO: Mercedes Malana 

WHAT: Forever 21 Sweetheart Floral Dress; Charlied & Paisley Wilma Bandana ($23)

WEAR: Floral dress + bandana. 

If you're looking for a dress outfit idea that channels peak glamourous with a pinch of Jackie Kennedy Onassis, without the effort, this idea is all you. Whether you’re going on a road trip or just running to the supermarket, pairing your favorite floral dress with a bandana is a must-try this summer. 

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Rouje Carlita Dress

WHO: Michelle Driscoll

WHAT: Free People Dress; Ella Stern Molton Disc Pendant ($164)

WEAR: Halter dress

We’ve seen Halter tops make their resurgence, and it seems that the dress form of this trend is also having a moment; of which, I’m very much here for. Pairing your favorite halter dress with a statement pendant is the perfect dress outfit idea for any zoom call, or run to the farmers market.

WHO: Chainky

WHAT: Zara dress and Buttoned Knit Top ($26)

WEAR: A tank underneath a strapless dress.  

Tube tops have been having their moment all summer, but if you’re averse to this trend and worried about how apropos it can be, then this summer dress outfit idea is the perfect alternative for you. Style your strapless dress with a tank to not only get more wear out of this dress style, but to make your look unique, and zoom-friendly. 

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Zara Elastic Trim Poplin Dress

WHO: Hayet Rita

WHAT: Maison Margiela Oversized T-Shirt Dress ($340); Cult Gaia Jila Flower PVC Sandals ($400); La Voûte La Pouchette ($125)

WEAR: T-shirt dress with your favorite shoes. 

Okay, this may seem like a simple outfit idea—but never underestimate the power of owning an oversize T-shirt dress. It not only looks good on everyone but can go with everything from heeled sandals to sneakers. It’s a staple piece that can be worn throughout the end of summer, and into the fall.

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Char Deep V-Neck Dress White

Char is a Black-owned brand you should take note of.

WHO: Bianca Foley

WHAT: Rixo Crochet Knit Midi-Dress ($172); River Island sandals

WEAR:70s inspired Knit Dress. 

Trends that feel straight out of the ‘70s have been trending all summer—and luckily for us, they can transition into the fall seamlessly. Investing in a midi-length knit dress is the perfect outfit idea not only to celebrate the end of summer but the beginning of fall. Whether you choose to pair it with your favorite sandals, or fall boots is up to you.

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Rixo Phoebe Crochet-Knit Midi Dress

WHO: Lee Ann 

WHAT: Lioness Dress Victory Boulevard Belted Mini Dress ($79); Fendi bag. 

WEAR: Blazer-inspired dress.

Season after season, the key piece that never fails is blazers. No matter the color or the pattern; this is a piece that works in all its forms—including as a dress. But if you find you’re overwhelmed with what blazer dress is worth investing in first, opt for neutral colors like chocolate brown (which is going to be big this fall).

WHO: Marche Robinson 

WHAT: ASOS off-the-shoulder dress

WEAR: Off-the-shoulder statement dress and your favorite hoop earrings. 

A list of essential dress outfit ideas to replicate before the end of the summer feels incomplete without including a timeless off-the-shoulder cut. Whether you opt for this style in a print or a solid color, this is a cut that deserves to be in the summer outfit rotation. 

Míe is another Black-owned business to watch.

WHO: Amaka Hamelijnck 

WHAT: Faithfull the Brand Ruffled Tie-Dyed Crepe Mini Dress ($169) and Tie-Dyed Linen Sunhat ($89)

WEAR: Ruched dress with a matching bucket hat. 

Matching sets have been all over Instagram all summer, and while there are so many different iterations of this trend, a cute way to cop it into your wardrobe this summer is by opting for a matching dress and hat. This outfit idea is not only trendy, but it’s too damn cute to not try to replicate before the end of the season.

WHO: Andrea Mun

WHAT: Nelly Flowy Button Dress ($80); vintage bag; Zalando shoes 

WEAR: White flowy sundress.

Is summer real every complete without busting out your signature white flowy dress? Whether it’s a maxi, midi, or mini—white dresses are a staple, that gives season after season.

WHO: Yusra Siddiqui 

WHAT: & Other Stories Maxi Dress; Cafuné Stance Bag ($585); Apercu Eyewear Vintage Tort Sunglasses

WEAR: Black maxi dress (bonus points for dramatic sleeves).

Not to state the obvious, but a summer wardrobe—and in my opinion summer bucket list—is incomplete without being able to wear a black maxi dress. If there were such a thing as a hero staple piece, it's a black maxi dress because you can style it any, and every way. 

 

WHO: Amy Nathalie 

WHAT: Loavies Black Zebra Print Wrap Dress ($40); Awfully Pretty Boxy Leather Coat ($72) 

WEAR: Zebra print dress and leather coat. 

The past few seasons have been filled with all varieties of animal prints; from cheetah, to snake to cow print; and it seems only fitting Zebra has its own little moment before the end of summer. But there’s no need to fear wearing Zebra print; you can style it with just about anything. We suggest pairing it with a leather jacket for a dress outfit idea that transitions from summer to fall with ease.

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Re:Named Zebra Mini Dress

Pair with BLANKNYC's Faux Leather Blazer ($119). 

WHO: Molly Beth

WHAT: & Other Stories Cat Eye Sunglasses ($19); Dr. Martens Metallic Platform Boots ($180)

WEAR: Tiered dress, preferably with puff sleeves. 

Call me basic, but I’m not tired of two things; tiered dresses and puff sleeves. This dress outfit idea is something you can rock not only at the end of summer but as Who What Wear reader, Molly Beth displays, you can transition it into fall by pairing it with your trusty boots.

WHO: Frida Becker

WHAT: William Okpo dress; vintage blouse; Gucci loafers

WEAR: Vintage dress, with a button-up underneath, and loafers. 

For vintage aficionados or granny trend fans, this dress outfit idea is right up your alley. Not only is pairing a dress with a blouse and loafers peak vintage aesthetic, but it’s a great look for transitioning your summer dresses into the fall.

Thrilling Vintage is Black-owned. 

WHO: Anysia

WHAT: Verge Girl Drawstring Mini Dress ($72); vintage leather trench and bag. 

WEAR: Fitted tank dress and full-length leather coat. 

While the idea of leather in August heat may already have you sweating, this is a dress outfit idea that lends itself well to the transition from summer to fall well. An outfit idea that allows you to get more use out of your favorite fitted dress and lets you pull out your coats for the new season? It’s a double, bucket list check-off.

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Lioness Military Minds Mini Dress

WHO: Michella Choi

WHAT: & Other Stories Floral Puff Sleeve Mini Dress ($59); Bottega Veneta High Ankle Chelsea Boots ($1100); F+H Madonna Charm Earrings Malachite ($115)

WEAR: Minidress and ankle boots. 

You know those minidresses you saved for nights out on the town? Well, you can still wear them before the end of the summer, and into the fall—in fact, I highly encourage you to give it a try. I beg of you, don't let the dress get dusty; pull it off the hanger, slip on your trusty ankle boots and pull up to your living room couch because that dress deserves to be worn.

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Mango Floral Puffed Sleeves Dress

WHO: Jasmine Fox-Suliaman

WHAT: Sabo Skirt Dress ($74); Converse Chuck Taylor All Star Move ($75); Missoma Gold Chain ($232); Urban Outfitters Rounded Rectangle Sunglasses ($20)

WEAR: Cutout dress + sneakers. 

Cut out dresses have been all over social media, and for good reason.  I can personally endorse this summer dress outfit idea; it’s not only hot but perfect for peak summer heat dressing. The moment I slipped into this cutout minidress I felt like summer was complete—and if that’s not the definition of crossing something off your bucket list, then I don’t know what is.

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Sabo Skirt Eilish Dress
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