Why Is Shopping For A Dress Such A Nightmare?

 
 

The Candidly Team

I have this habit of getting really hyped about the necessity of shopping for a dress. Whatever the occasion may be, I go in VERY excited by the possibility of picking out the ideal, one-and-done dress of my dreams.

The only problem? I never find it. I search and scroll until I completely lose steam. To me, the perfect dress may as well be the lost city of Atlantis. The stuff of myths. 

Why is this task so weirdly impossible?

I mean, I get it. Dresses have to work double duty to look good on both the tops and bottom halves of our body. They’re asked to meet all kinds of criteria for degrees of formality, flattery, fit, and flounciness.

Imagine seeking a single clothing item that covers here and shows off there, that feels amazing but isn’t frumpy, and isn’t so blah that no one notices but isn’t so bold that we wind up wanting to hide under a pashmina all night.

But before we give up and go dust off the same dress we’ve been deeming acceptable for way too many occasions in a row, consider this:

Amazing, criteria-meeting dresses DO exist. They’re out there. We just don’t want to have to go deep-sea diving to find them every time a Paperless Post enters our inbox.

Which is why, we’ve created a list of truly winning dresses for every type of “thing” you’ll ever need a dress for. After years of hunting through bins and brands, here is our own little book of best dresses that are almost foolproof in their respective categories.

1. GREAT FOR CASUAL/ DAYTIME

 

Marcella Clara Dress

Let’s not save the best for last for once. This dress is THE most flattering, most glorious feeling maxi dress around. The top is like a soft, stretchy tank, while the bottom is light, airy, and sooooo much fun to wear. We call it an “everyday dress,” but it could just as easily be worn out at night with a pair of chic sandals, and THIS non-black handbag.

Price: $108


 

Everlane The Ribbed Tank Dress

Finally, a ribbed midi dress that doesn’t make us feel like we’re in a swimsuit. This dress has hold. It has stretch. It isn’t flimsy and cheap-looking. It smooths over curves and isn’t too tight. You can see our little trick for styling it HERE. But if you’ve always wanted a carefree fitted midi to stroll around in, raffia tote thrown over your shoulder, this is your girl.

Price: $78


 

Quince 100% European Linen Button Front Dress

Quince has found a way to take all the things we want to wear in all the materials we want to wear them in and weave them into reality without charging us a fortune. This dress is an absolute staple in our warm-weather wardrobe. We can wear it to work or just as easily throw it on with comfy sandals and head out for a picnic.

Price: $50


 

Zesica Women's 2023 Bohemian Floral Printed Wrap Dress

A maxi wrap dress that comes in a sea of prints, so we essentially have the perfect thing to wear every weekend day of our lives.

Price: $46


 

2. GREAT FOR COCKTAIL

By Anthropologie The Maya Ruched Cowl-Neck Dress

We love the idea of wearing a long fitted dress up until the moment we put one on and just feel sort of self-conscious, un-flattered and “meh.” Not so with this dress. The thick stretchy material looks luxe but feels like our softest most unbelievably smoothing yoga pants. Then there’s the ruching, which is probably the biggest hack for making tight things easier and more flattering on all of our many curves. It has sizes in plus and comes in every color we could desire.

Price: $160


 

AYR The Extra Extra

This dress is the stuff of summer soirée dreams. The smocked waist coupled with the deep v-neck are endlessly flattering, while everything else is just an easy, breezy, billowy joy to wear. It’s more of an investment, but it’s truly the dress you’ll want to wear out more than any other.

And AYR was kind enough to give us a code to share. Use code CANDIDLY15 to get 15% off.

Price: $325


 

3. GREAT FOR CURVES

Maeve The Cecily Fit & Flare Sweetheart Dress

We wrote an entire article about curvy dresses, because we’re honestly tired of dresses that don’t understand curves. This one, however, does…in the most thorough sense. The neckline is perfect, the material has a magical kind of stretch that smooths and holds us in in the precise way we want it to. The skirt isn’t too tight, but it’s fitted enough to make it look clean and chic. It’s the little black dress of our longstanding dreams, but it also comes in prints. Just look. And it, of course, has sizes in plus.

Price: $170


 

J. Crew Striped puff-sleeve midi dress

Smocking is one of our favorite things (right up there with ruching) when it comes to feeling comfortable and flattered by the clothes we wear. This dress smooths curves up top, floats in the breeze at the bottom, and has little puff sleeves, because we don’t always love going sleeveless.

Price: $49.50


 
 

4. GReat for formal occasions

Reformation Winslow Dress

I dare you to find a single woman who tries on this dress and doesn’t feel like she immediately looks good. It’s draped to perfection, yet smooths its way over curves. The style comes in extended sizes and fits the bill for a million occasions. Just don’t buy it if you’re not comfortable with compliments.

Price: $348


 

Norma Kamali Diana Dress

We could go on and on about great wedding guest dresses, but if you want the PERFECT one, this is it. Can’t be beat.

But if you must keep searching (or just have way too many weddings to attend this year), we also made this very lovely and much longer list HERE.

Price: $215


 

Modern Citizen Mila Layered Tank Dress

We’ll let you in on a secret. We’ve written about this dress before, and you guys have been ALL about it. We see what you click on 👀. But there’s good reason. It’s flowy and Grecian. It’s the prettiest Beyoncé’s Lemonade color, and the tie waist makes it sooooo complementary. It’s the easiest dress-up dress on this list. And then, there’s the price.

Price: $45


 

5. GREAT FOR COMFORT

Hill House The Ellie Nap Dress

Sure, you could write this off as something you only wear at home, because it is that light and cozy, but that would be such a waste. This dress is excellent to wear out, even to weddings – even braless – we’re serious.

Price: $150


 

Skims Soft Lounge Long Slip Dress

We’ve been raving about this dress ever since we ourselves slipped it on (see HERE) and realized that in addition to being wildly comfortable, it looks gorgeous on curves. And because it’s long with the chicest neckline around, we can dress it up and wear it to “events” even though we feel like we’re in pajamas.

Price: $78


 

7. Great For Work

Quince Tencel Jersey Midi Wrap Dress

Remember a million years ago (last year) when our work functions were all on Zoom with us in sweatpants paired with a dressed-up top? Well, if anyone else is madly dashing to find dresses we can wear to work while still having that sweatpant feel, here is the most buttery soft wrap dress you can imagine. It honestly looks as good as it feels.

Price: $60


 

Boden Side Ruched Jersey Midi Dress

We recently discovered this British brand that apparently everyone in the UK has known about for ages, and it’s become our go-to for perfect-fitting staples like this dress. The ruching on the side makes it supremely flattering, but it still has those sleek lines we love in a pencil dress. Plus, it feels like a literal t-shirt, so we’d pretty much sleep in it. And it sizes up to 22.

Price: $98

 

 
 
 
 

At The Candidly, we try a lot of stuff so you don’t have to. We only recommend things we truly love, and that we think you’ll love, too. All products are chosen independently by our creative team, and all details reflect the price and availability of products at the time of publication. If you buy something we link to, The Candidly may earn a commission.
We have to eat.