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Feb 13, 2024

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Every item on this page was chosen by a The Pioneer Woman editor. We may earn commission on some of the items you choose to buy. Just throw them on and look effortlessly cute. Don't get us wrong, we

Every item on this page was chosen by a The Pioneer Woman editor. We may earn commission on some of the items you choose to buy.

Just throw them on and look effortlessly cute.

Don't get us wrong, we absolutely love shopping for seasonal outfits. But there's something about having go-to items in your closet that you can wear all year long that feel like such a worthy investment (even when you don't spend that much!). This is especially true during transitional weather where you're wondering if it will be hot or cold or both during the day. Ugh, we know! That's why a button-down dress is the solution.

Now you may be picturing the classic shirtdress style that is basically a button-down shirt in a longer length, and we certainly have plenty of those on this list! But there are also flowy midi and maxi dresses and cute floral dresses, too. They may differ in style and length, but they do have one thing in common: their versatility. You see, in the warmer weather, they can be worn as is with a pair of comfy flats and not much else. But as the weather gets chilly, all you have to do is get really good at layering clothes, and you can wear them all the time.

And while there's nothing wrong with wearing bright, bold colors any time of the year, the options here are more neutral, making them appropriate no matter the temperature outside. They're like a T-shirt dress or a denim jacket―basically, you can just throw them on and look effortlessly cute. And isn't that what we want all year long anyway?

If you're going to pick one option and stick with it, a classic collared shirtdress in a solid is the way to go. There are ten colors to choose from, and each would be great over a pair of leggings, tights, or even jeans if you want to cover your legs.

A little black dress is always a good choice, and it's really easy to see why this is a bestseller. It's the right amount of tailored and flowy, and plus it's 100% cotton, making it seasonless.

Just like a blue and white pinstripe is a seasonless choice in a shirt, it is in a dress as well! Throw a sweater over your shoulders in case it gets chilly and a pair it with loafers for a timeless look.

A soft and lightweight fabric like this can be worn year round because it flows so elegantly. This would look as cute with pair of boots as it would strappy sandals. And while we love the mustard yellow, there are dozens of other color options to choose from.

When is a pretty print not a good idea? This lightweight poplin option has added feminine flair with a cute flounce hem and tie waist. The sleeves come with roll cuffs but can be rolled down to be full length, too.

Opting for a button-down that's less traditional is equally as fashionable. Look at this fun, flowy midi! It comes in lots of fun prints and has a long sleeve option, too. Either would look so cute with a jean jacket on top!

You could go for a classic denim shirt silhouette or try something a little more on-trend like this puff sleeve, tiered mini dress. It's available in petite, regular, and tall sizes, so literally everyone can wear it!

You might think it's hard to find a plaid that you can wear all year, but we found one! Picture this as your Labor Day dress and then as the seasons change, add a turtleneck and some tights.

Silk that doesn't have to be dry cleaned? That's just one of the reasons this dress gets five stars! The olive color is basically a neutral for all seasons, and that silhouette is a modern yet classic choice.

We've got another five-star reviewed print! With a tiered A-line skirt and a flattering tie waist, you'll love wearing this all the time. It has a little bit of stretch in it to give you all day (and all year!) comfort.

A polkadot dress is always a good thing to have in your closet. They never go out of style! And we love this midi version that you can wear as is with a fabric belt or change it up to leather for different look.

Another way to wear a denim dress is to try a different color! This faded pink is so fun, but they have it in all sorts of options. They are all made of viscose, making them drapey and soft.

Navy and white stripes are a classic choice, as is Lands' End for just about any item of clothing. This short sleeve pick is great for wearing to work, church, or anytime you want to look a little more put together.

Shades like camel look good on practically everyone in any season. We love the more modern covered placket and airy swing of this option. It is the perfect dress to accessorize however you want!

Available in petite, regular, and plus sizes in a ten prints and solids, this dress has an option for every shape and style. It's made of 100% cotton and has a slightly looser fit, so you'll be comfortable no matter which one you choose.

AnnMarie Mattila is the Commerce Editor for The Pioneer Woman, covering products ranging from home, fashion, beauty, and more.

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