Shopping·9 min read

Investment-Worthy Dresses You’ll Wear Past the Event

Design: theSkimm | Photos: Anthropologie, Reformation
March 19, 2024

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Finding the perfect dress for an upcoming event? Something to celebrate. But finding a dress you love so much you’ll want to RSVP “yes” to every future social engagement? Even better. These are the dresses you’ll likely have to shell out a little more for — thanks to features like higher-quality materials and handmade details — but since they won’t languish in your closet forever after wearing them once, they’re well worth the investment. We’ve found dresses appropriate for every type of occasion, from baby showers to black-tie weddings, that you’ll keep wearing for years to come.


A metallic number that goes perfectly with golden hour…

Wear this slinky strapless dress to a spring or summer wedding, then with sandals on vacation or with a blazer for date night. It’s made of a stretchy fabric with a built-in bodysuit underneath, so you won’t have to worry about finding the right undergarments. PS: This cult-favorite style comes in a ton of different lengths, colors, and materials — find more here. ($265, Anthropologie)

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Free People

A floral masterpiece you’ll never want to take off…

Okay, hear us out. We know this dress is pricey, but LoveShackFancy makes some of the most beautiful floral dresses we’ve ever seen. This one is no exception, from the deep V-neckline to the dramatic ruffle down the middle. The blue and white metallic floral wears well in the spring and summer, but could also be layered over a white turtleneck for an icy winter look. ($695, Free People)

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A twist on the classic slip dress…

Slip dress, you’ll always be famous. This one is eye-catching, thanks to the subtle keyhole at the bust and contrast piping. The low back lets you show some skin and ensures it’ll be a fun choice whether you’re headed to a wedding or somewhere tropical. It comes in four colors, but we’re partial to the unique olive and black colorway. ($280, Revolve)

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A romantic linen midi dress…

When temperatures start to rise, you’ll reach for this dress time and time again. The scoop neckline with a little bow and cinched waist bring “Bridgerton” vibes, and the smocked back ensures the perfect fit. You can’t go wrong with any of the colors or patterns, but if we were a bride, we’d grab the white and pair it with bow pumps for a rehearsal dinner or casual ceremony. ($278, Reformation)

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A little black dress that stands out from the rest…

No boring LBDs here. The one-shoulder style is pure glam, and it’s nicely balanced by the thigh-high slit on the other side. We love that the sleeve can be cinched, so you can wear it how you want. It’s a staple wardrobe piece you can accessorize a thousand different ways for almost any event. ($59, Eloquii)

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Free People

A dress that makes us want to twirl…

This dress is giving “fell down a rabbit hole into a magical world” energy, and we can’t get enough. We’re suckers for a blue and white floral print, especially when paired with romantic puff sleeves. Plus, we love that it has underwire cups so you might be able to go braless. Snap this up before it’s gone; Selkie dresses don’t tend to stay in stock. ($325, Free People)

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Abercrombie & Fitch

An Abercrombie & Fitch dress that has never let us down…

Have a hot date? This dress. Sister’s baby shower? This dress. Headed to the office and not sure what to wear? This with a cute jacket on top. The reason this midi is one of our closet’s hardest workers is how well it fits; the smocked back cinches our waist without being too tight and the adjustable straps help us find the perfect fit. ($69.99+, Abercrombie & Fitch)

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A workhorse dress from one of our favorite brands…

Staud can do no wrong. This dress is made out of ribbed knit fabric that’ll move with you. The V-neck with buttons down the front lets you customize how much skin you want to show, and the simple, sophisticated style can be worn with everything from sandals to sneakers to boots. ($245, Shopbop)

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A black maxi dress that’s good to have on hand…

This simple, sexy maxi dress is body-skimming with a V-neck, fitted waist, and slight mermaid skirt. You’ll want to have this stashed in your closet for when you get a black-tie wedding invite, are tagging along to your partner’s holiday work party, or dressing up for New Year’s Eve. Make sure to wear it with a great pair of heels. ($99, Lulus)

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Saks Fifth Avenue

A Staud mini dress we’ve worn so much we need another one…

When we saw one of our favorite Staud dresses is now available in pink, we knew we had to include it. We’ve worn this toile dress on a bachelorette weekend, to an engagement party, and on a shopping day around town. The best part is that the cotton poplin flare skirt isn’t too short but keeps you cool on the stickiest days. It also comes in a midi version. ($225, Saks Fifth Avenue)

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Anthropologie’s bestselling maxi dress…

From the flattering V-neck to the cinched waist, we can see why this cotton dress has so many fans. It’s comfortable, pairs well with almost any shoe, and goes from the office to an after-work happy hour with ease. The new lemon print is the perfect addition to your spring dress collection. ($168, Anthropologie)

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Mara Hoffman

A gauzy dress begging to be taken on vacation…

Between the bright red color, pretty draping, and open armholes, each detail of this breezy midi dress is better than the last. Wear this out to dinner on your next getaway, then to a summer wedding where you know you’ll be dancing the night away. The removable belt creates structure without sacrificing comfort. ($295, Mara Hoffman)

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A showstopper if we’ve ever seen one…

This maxi dress has a sheer, stretchy overlay with a mini-length hem underneath (aka, it’s comfortable) and features a bold floral print. We love the contrast trim on the sleeves and neckline and would pair it with an updo for even more drama. One thing about Alice & Olivia dresses is they really hold up, so you’ll be wearing this one for years. ($495, Nordstrom)

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Banana Republic

A satin midi dress to wear to work and beyond…

When we imagine a dress that will take you straight from the office to happy hour, this is it. The satin fabric dresses up this classic cap-sleeve silhouette, and the shirring at the side ensures a just-right fit. When 5 o’clock hits, lose the blazer and let it stand alone. ($60, Banana Republic)

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A slip dress we’ve been wearing for years…

Now that J.Crew has been having a major comeback, we’d be remiss not to include the slip dress that started it all for us. It’s the classic ’90s version, but we love that this one has adjustable straps. We’ve worn it at the beach, with a denim jacket, and layered over a tee. There are a million ways to style it and several colors to fall in love with. ($64.99+, J.Crew)

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