So These Under-$100 Dresses Are Categorically Perfect

There are few things that make me feel more confident in a dress purchase than knowing I’m going to be able to wear it constantly. Certain dresses lend themselves to numerous styling possibilities, making them foolproof wardrobe investments. In order for me to establish this level of confidence in a dress purchase, there are a few factors I consider. If the style in question meets all three of my requirements, I consider it to be categorically perfect.

What are the three criteria on my checklist, you ask? First there’s versatility. Can I wear this dress to multiple events and style it in new ways each time? The second is if it’s on trend. Obviously, I want to look and feel current even if it’s something I plan on wearing and keeping for the foreseeable future. And the last box it needs to check: Is the color or print appealing? Will I be sick of this after two wears, or is this a print that will stand the test of time?

It’s that easy. To give you some examples of what I’m talking about, and maybe inspire you to make your own checklist to determine if an item is categorically perfect, I’ve rounded up the 24 best dresses that fall under this category below. I’ve also kept them all under $100 to prove this theory can be applied to affordable items just as easily as it can to investment pieces. Happy shopping!

The tie-waist detail is so flattering.

Pairs well with boots, sneakers, and heels.

This will look beyond chic with tall boots.

The ultimate throw-on-and-go dress.

Is there anything cozier for fall?

Perfect for the office. 

Talk about a versatile dress.

Just as cool for the office as it is for happy hour.

You could even wear this to a wedding. 

Define your waist with a chic belt. 

This dress was made for tall boots.

A cinched waist you don't even have to think about. 

The dreamiest date-night dress.

I can think of a million places to wear this one. 

This one can be dressed up or down like that.

This would be so cute paired with sneakers.

A sweaterdress is always a good idea.

I bet this one is beyond comfortable.

A bold print to embrace. 

The ultimate LBD.

Animal print is the trend that keeps on giving.

How pretty is this sleeve detail?

A wrap dress is so timeless.

An LBD with sleeves will be one of your most-worn pieces.

Next up: I went on a shopping spree for pretty tops—these 19 made the cut.