My favorite summer dresses for 2021

I read a recent theory that we're conditioned as children to "love" summer because of the three-month break we get from school; in actuality, it's hot and miserable, so what is there really to love? For one, I enjoy that it's still light after 8pm. But more importantly, summer is dress season. I tend to wear one nearly every day—nothing is easier, more comfortable (and breathable), or cuter in warm weather—and I always scoop up several new ones at the start of the season, because, hey, my name is Cheryl Shops. So on that note, here are my favorite dresses for summer 2021.

The breezy swing dress

Full disclosure: I work for Old Navy, and I bought this dress because I had to make an in-person presentation to our leadership team and wanted a little bit of extra luck. Not only did my presentation go well, I totally fell in love with this dress. The quality is pret-tay nice for Old Navy—the fabric is 100% cotton with detailed embroidery at the hem and fun tassels at the straps, which have a tie and are fully adjustable. I've already worn it to wine country, to a picnic in the park, and for a day of working from home (which is every day, TBH), and I'll definitely be taking it on several of my weekend trips this summer. Highly recommend! This dress is true to size but is meant to be breezy and swingy; I'm in my usual size small. 

OUTFIT DETAILS: Old Navy swing dress | J.Crew quilted jacket | Ganni hat | Birkenstock EVA Arizona sandals

The puff-sleeve mini (a.k.a. the nightgown dress)

As I've been mentioning in the last several posts, I'm really trying to drag myself out of the boring beige clothing rut I've found myself in, and when I saw this Target dress (yes, Target!) featured on one of my favorite Instagram accounts, Things I Bought And Liked, it felt like an inexpensive risk to take. This dress comes in a bunch of colors and prints—several of them in very safe options like white, black, and a subtle blue stripe—however I decided to go for the same one that Ms. TIBAL owns, a very outside-my-comfort-zone lavender and orange floral print that strangely reads kind of pink from afar. I think I love it? The dress itself is very comfortable and flattering; my fortysomething arms are very appreciative of the puff sleeves. It does kind of look like a nightgown, but I'm not mad at that. Oh, and did I mention it's only $25 (and 100% cotton)? I'd err on the side of sizing down, but know that the shoulders and bust are a bit snug in relation to the rest of the body; I'm wearing my usual size small. 

OUTFIT DETAILS: Gap denim jacket | Universal Thread babydoll dress | Birkenstock sandals (similar here

The Target designer collab dress

I don't know if I will ever get tired of Target's designer collaborations, especially when they're as good as this year's featuring CFDA rising star award winner Christopher John Rogers. This green dress got a lot of love on Instagram and in my Calistoga post, so I wanted to give it a little more attention here. This is also a color and silhouette that I wouldn't normally wear, but after seeing it on a few influencers (plus a ringing endorsement from my coworker), I decided to give it a chance. It's a lot of dress—there's some rustle to it, and a lot of fabric—but I love it. Now I just need more fabulous occasions on which to wear it. In the meantime, I bought this floral maxi too, which I may love even more. Both run true to size (I'm in a small in the green) and both are an incredible deal. 

OUTFIT DETAILS: Christopher John Rogers dress (also love the floral version) | Mango bagBirkenstock EVA Arizona sandals

The smocked maxi dress (a.k.a. the nap dress)

I've already dedicated an entire post to this plaid maxi dress, but it's so good—and was so many years in the making—that I had to feature it again. The ladies in my Facebook group call this style a "nap dress" (not to be confused with the nightgown dress above), and while it probably is comfy enough for a snooze, it's also great for brunch, wine country, working from home (sense a pattern here?), or general lounging. And while I love the wackadoo color scheme here, it also comes in slightly more subtle combinations too. 

OUTFIT DETAILS: Ganni dress (also love this color and this one) | Sole Society hat (similar here) | Mango bag (current version) | Mango sandals (similar here

The classic white linen shirtdress

This dress isn't new—in fact it's one of the first I featured here—but it's one of my summer go-tos year after year. There's just something so classic about a white linen shirtdress, and the fact that I've had this one for so long vouches for its quality. Gap keeps bringing this style back, and while this year's version is technically a tunic, it's long enough to be a dress or at worst, a swim cover-up. Then again, I've worn mine as a tunic too. This one also runs true to size, allowing for a relaxed fit that's just totally perfect for summer. 

OUTFIT DETAILS: Free People blazer (current version) | Gap dress (current version) | Staud bag (current version) | Birkenstock sandals (similar here


Mica said...

You have so many gorgeous summer dresses! I really like the first on but that floral Target one has to be my favourite- what a cute print and colour combo! It's so nice with the denim jacket :)

Hope you're having a wonderful day :)

Away From The Blue

Barbara Lee said...

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Nancy 's Fashion Style said...

I really love the longer ones, but they all look great!

Lovely said...

Such fantastic picks! Love them all!

Laura B said...

All of these are so cute on you! That green one is my favorite!

Jessica Jannenga said...

Love all these styles! The old navy one is so cute, I just love gingham and it looks so comfy too. My favorite is the plaid midi dress you wore! I also love the Target print but they dont have it anymore. Nothing like flowy dresses in the summer.
Have a great weekend, and thanks for linking!
jess xx

Gail Is This Mutton? said...

You certainly have an eye for a pretty summer dress! My favorites are the green dress and the plaid maxi. Thanks for linking at #WowOnWednesday.

Shelbee on the Edge said...

Cheryl, these are all such wonderful dresses! I really like the gingham one and the green one. But I would definitely wear all of them in a heartbeat! I am glad that your Old Navy presentation went well!


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ava fin said...

Summer dresses are the epitome of effortless style and comfort! how to watch netflix on facetime It's great to have favorites that make the season even brighter. Do you have a particular style or color you lean toward?