15 Dress Styles Fashion People Wear Over and Over Again

Question: Is there one thing you can't have enough of in your wardrobe? For some, the answer may be a great pair of jeans, or maybe it's shoes. But I've always been a devoted fan of dresses. No matter what season it is, I'm about that life. And while I always make room for a new frock, I have to admit that there can be a limit to how many dresses one should own (even if it's only imposed by real estate). When you can't have every type of dress imaginable, you have to be able to edit it down to a thoughtful capsule

So in that vein, I've scrolled through Instagram for hours to identify 15 types of dresses that are worthwhile investments. Each style's worthiness was determined by its popularity among the fashion set, versatility, longevity, and ability to fit seamlessly into any wardrobe. Whether you consider yourself a modest dresser or live for a special occasion, you'll be able to find at least one type of dress that's worth the closet space for you. 

1. Chunky Sweaterdress 

Think dresses aren't something you can wear in the dead of winter? Think again. When it's cold outside, the fashion set isn't afraid to shy away from the staple, so long as it comes in the form of a chunky sweaterdress. 

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Add a wool wrap coat, and you've got the perfect winter outfit. 

2. The Relaxed Ribbed Dress

Don't be confused: A ribbed dress is different from the chunkier versions depicted above. While both can be knitted, this staple is typically made from lightweight fabrics and errs on the more casual side. This style is typically the go-to dress for the fashion set during transitional weather in the spring and fall. 

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This dress will look great with boots in the winter and sandals in the spring. 

3. Slip Dress

Another beloved type of dress with the fashion set is the slip dress. While some may think this style is a little "risqué," but when styled right, it can be one of the best staples in your closet. 

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I'm obssessed with the lace bodice on this slip dress. 

Trust me when I say this is one of the most flattering slip dresses you'll ever own. 

4. The Everyday Maxi Dress

If your style errs on the more modest side, then there's one type of dress that definitely deserves a spot in your wardrobe: the maxi dress. Not only is this style easy to wear, but you can wear this year-round. Simply opt for thick fabrications in the colder months styled with layers and light cotton and silk versions in the warmer months. 

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Staud's maxi dresses are my personal favorite. 

5. Puff-Sleeve Dress

You can't round up a list of dresses styles the fashion set loves without mentioning the puff sleeve. While this dress may have gained popularity a few years back, it's become a perennial staple in women's wardrobes around the world. 

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The stitching on this dress is just *chef's kiss.*

6. LBD Rebooted

It's no secret that the little black dress holds a special place in closets everywhere. But over the past few seasons, we've seen more of the fashion set embrace versions of this staple with subtle twists. It's about taking the simplicity of this dress and giving it a fresh reboot with unique details like cutouts, playful necklines, and impeccable tailoring. 

The contrast-trim neckline takes this black dress from simple to stunning. 

7. The Party Mini

Whether it's the holiday season or mid-June, every fashion person knows that having a dress you can pull out at a moment's notice for that last-minute invite is a must. In those moments, a fairy godmother isn't going to save you, but a minidress will. Our rule of thumb is to invest in a minidress with fun details that you want to wear repeatedly. 

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The party won't start until you walk in wearing this dress. 

8. The Work-Friendly Midi Dress

Let's be real: Discerning what to wear to the office after years of prolonged social distancing isn't easy. Luckily for us, one type of dress is the unsung hero of every work wardrobe: the midi dress. When in doubt, a midi dress with a high neckline will always take the work out of choosing what to wear to work. 

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The neckline on this dress is not only conservative enough for the office, but it's downright chic. 

9. The Iconic Wrap Dress

Another dress that works well both on and off duty? The wrap dress. What's wonderful about this iconic style is its versatility—it comes in everything from ribbed knits to luxe leathers and neutrals to vibrant hues. Plus, it's universally flattering, making it the easiest piece to incorporate into any wardrobe. 

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You can't talk about wrap dresses without mentioning the brand that made them popular—ahem, DVF. 

I love how the buttons on this dress further accentuate the tied-in waistline.

10. The Classic Sun Dress

While dresses can be worn year-round, it would be dishonest as a dress fan not to admit that one style can't be beaten: the sundress. It is possibly the only staple you need to get you through those insufferably warm months. The key is to invest in a poplin dress (made from cotton or linen) that you love because it will brighten up your life every time you wear it. 

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The shirring on this ensures it will look ultra flattering while you wear it. 

11. The Printed Frock

Print trends may come and go, but printed dresses? That's a whole other thing. No matter what's happening on the runways, people continue to love (and wear) printed frocks in the real world. It's the perfect way to add a little pop to any wardrobe, so it only makes sense this dress style would continue to be beloved. 

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Rixo's printed dresses are beloved among the fashion set. 

Animal prints are trending right now, making this dress the ideal purchase. 

12. The Little White Number

Until this point in the story, one could argue that every dress style listed was easy to wear—but this style isn't necessarily that. Not only are there preconceived "rules" about wearing white that some people still like to follow, but keeping this color clean isn't easy. However, if you're up for the challenge, there's no better dress style to invest in than a little white number. Whether you spend $100 or $1K, this style always looks luxurious and will bring a little dose of luxury into your daily life. 

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Tove's cotton dresses are a long-term investment that the fashion set swears by. 

13. The Luxe Leather Dress

Can't picture yourself wearing a white dress but still want something luxurious? Enter the leather dress. Anyone that loves leather trousers or jackets is already aware of the power of this fabric. But for those who have yet to invest, consider this your sign to do so. 

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Everything about this dress is perfect—the drop waist, the square neckline, the box pleats.

Note the cutout details on the side of this dress. 

14. The Shirtdress

If one of your favorite staples is your oversize button-down shirt, you need to consider investing in the dress form too. The shirtdress is not only a piece that can be worn in professional settings, but based on fabrication and styling, you can wear this piece year-round. 

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Now here's a dress that could pass for being a designer piece. 

You'll want to zoom in to see the contrasting stitching on this button-down dress. 

15. The Evening Dress for Every Occasion

You've made it to the end of this story, and hopefully by now, you've been convinced of the importance of owning at least one type of dress you love and can turn to throughout the year. And while we don't always have special occasions every day, this style is a must for anyone wanting to build a capsule wardrobe or to stop spending money on a new outfit for every wedding they're invited to. Like every other dress in this story, you'll want to invest in something that's not only classic but that you love. Because no matter what type of dress you're wearing or where you're going or what the weather is, if it's not a style you can wear time and again, it's not worth your time. 

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You can customize this one so that it's the perfect fit.

Who wouldn't want to wear this dress multiple times?