Three Comfy Summer Dresses and How to Dress Them Up & Down!

We’re publishing Thursday’s post a littttlee bit early because these dresses are selling out FAST! And I wanted you all to be able to shop them quickly in case they sold out! 

In talking to so many of you via DM, it seems like EVERYONE is struggling with “transition” style–AKA–how can you dress comfortable (because after 2020, there’s just no way we’re going back to uncomfortable clothing amiright?) but cute! Like, what DO we wear to brunch again? On dinner dates!? We are all out of practice when it comes to getting dressed! 

There is nobody who understands this more than me, the almost 9 month pregnant lady. I was feeling this majorly–I needed a couple more VERY liberally cut dresses to get me through until LR gets here, and through a postpartum summer. (But also, I didn’t want to buy MATERNITY dresses)–luckily, a few frocks from Old Navy caught my eye, and they all turned out to be complete gems–so I shot them for you really quick this afternoon, and here we are! 

Scroll down for three (very budget friendly and comfortable) summer dresses, and several ideas on how you can style them out and about this summer! 

I fell in LOVE with this dress at first sight, and really hoped it lived up to my expectations. Good news–it DID! It’s not only the happiest yellow color, a perfectly cut silhouette for summer, totally NOT see through (it’s lined!), but it’s SO SOFT. A lot of dresses that are this style are made of poplin, which, if we’re being honest–I just can’t deal with right now. 😂 SOFT and BREATHABLE are the name of the game. If you’re feeling the same way, you’ll love this dress. 

Sizing: Very generous in sizing. I went up a size to medium because my ribcage expanded in pregnancy and a lot of my current dresses are too small in the ribcage, but I definitely could’ve gotten away with a small (which is my pre-pregnancy size). However, I don’t think it’s TOO big either and I appreciate the fact that it’s looser! 

How to style it: 

With sneakers and a cross-body: 

You might not think a dress this girly could be paired with sneakers, but that’s what I love about these sneakers in particular (and why they made my favorites list of best white sneakers) is because of the cute D’Orsay cut-out–I think they’re more feminine than your standard pair of sneakers and therefore, they pair PERFECTLY with dresses, especially if the typical “Tomboy” look isn’t usually your thing! Read more about them right here! 

Additionally, this cross-body is convertible into a belt bag (you’ll see how I styled it as a belt bag further down in this post!) It’s the perfect size to hold just the essentials while ensuring you are always hands-free! Plus, it’s on sale, AND you can get 25% off the sale price with code JESSKEYS25. The brand that makes it is one of my absolute favorite brands with such an amazing story–read more about ABLE in this post! 

With a summery headband and bow heels:

I’ve had this headband since last summer–it’s from Alice & Wonder and I’m so glad she re-stocked it this year! It’s so cute and I wear it ALL the time. It’s the best because you don’t actually have to do your hair, but you look really cute and polished. (Plus, when the weather is so hot, it’s nice to have your hair off your face!) 

I also just ordered these adorable shoes (they were basically a push present to myself 😜) because I ADORE my Loeffler Randall Penny heels and have been wanting another pair in the lower version, the Emilia. They are so comfortable, and love that they easily slip on! I like that this pair is still neutral but has a pop of pattern, too! They run TTS in my experience but some suggest to size up if you have wider feet! (FYI, the color is called “mustard” but it’s really more of a tan!) 

With strappy sandals & woven belt:

This dress also looks super cute with a belt if you prefer a look that is more cinched at the waist! This is just one more way to make it a little more dressy/interesting! (Note, make sure to measure when you’re ordering this belt for accurate sizing! It’s from Amazon and SO cute–pairs perfectly with all my summer dresses.) 

I wore these sandals every night in Charleston and walked miles in them and they were great! (If you have any issues with sandals or new shoes rubbing, I recommend a friction/anti-chafe balm (I use MegaBabe’s thigh rescue to prevent blisters as well as chafing anywhere, it’s awesome!) The leather on these sandals is very soft though, so they don’t cut into you like a lot of sandals do! (My feet always need a couple wears to “adjust” to new sandals, but I was pleasantly surprised by how comfy these were!) 

They’re such pretty sandals, go with everything, from jeans to cocktail dresses and everything in between! (Great wedding shoes too!) 

The earrings I’m wearing are old, but this set of four pair from Amazon is so cute and has a pair that are very similar! 

I saw Kendi post this in one of her recent try-on’s and I thought this looked like the PERFECT dress for me right now. I was right. I will be very thankful to have this for the next month and throughout the summer! Sometimes shirt dresses can be pretty short on me (I’m 5’6) but this one is the perfect length. 

Sizing: Also very generous in the cut/fit. I ordered my regular size (small) and it fits great! Love that it’s not so loose that it looks like a tent, but is plenty roomy for comfort. 

How to style it: 

With gold Birkenstocks and a cute headband: 

Above I would label as my “it’s hot AF out and I just need a comfy, loose outfit” look. 😆 A look we ALL know well as the weather heats up! It’s why we love t-shirt dresses so much–you don’t need much to make them look cute! I just got these gold Birkenstocks on Grace’s recco–they typically sell out SO quickly but they’re still available right now on DSW and Zappos! They just came today so I’m still breaking them in, but I love that they’re supportive (I have very flat feet) and they slip on easily (ideal in pregnancy and with a newborn, haha!) 

With slip-on Rothy sneakers (c/o) and a leather backpack: (c/o) 

One of my favorite outfits of this bunch! (Okay, it’s pretty hard to choose, but I love this combo!) featuring some new-to-me staples that I am IN LOVE with. First, Rothy’s slip-on sneakers. I know you all have been trying to get me on the Rothy’s train for YEARS. (I love the look of their flats, I just haven’t really had a NEED to buy a lot of flats because I don’t work in an office!) but they gifted me this pair of slip-on’s and I can’t believe I held out for so long. They’re so great! I don’t own any slip-on sneakers, and I love the beige color and they have the cutest striped detail on the back. All their shoes are made from recycled plastic water bottles and they are machine washable. (Which will be ideal with LR 😜 Somehow I think it’s going to become harder to keep my shoes clean.) They run TTS in my experience! 

Second, is this leather backpack from ABLE. I really don’t think the website does justice to how beautiful and functional this bag is. I had been eyeing it for a few months, wondering if it would make a good diaper bag. (I couldn’t bring myself to buy an ACTUAL diaper bag–I know they have cute ones out there, it just didn’t feel like me!) Well–let me tell you, it’s UNREAL. It’s so roomy, the organization is fantastic (has a laptop sleeve AND the outside side pockets are big enough for my big hydro flask)! 

It was my personal item on the plane to Charleston, so it’s amazing for travel. It’s my go-to when I’m heading to the coffee shop to work for a few hours (I can finally do that again! 😭) and it fits ALL of LR’s essentials for her diaper bag. I can’t recommend this bag enough, no matter if you’re a mom or not! (Also, you can get 25% off when you use code JESSKEYS25 at checkout!) 

With sneakers, jean jacket (c/o) and belt bag: 

Another great, casual way to style your t-shirt dress! We’ve already touched on these sneakers and the belt bag, but let me tell you more about the denim jacket! You saw me rave about this jean jacket here (see my ABLE highlight on stories for a try-on!) it’s a great layer to throw on if it gets chilly at night, and it has the perfect amount of distressing to add some visual interest to the outfit. (Plus, it’s the SOFTEST denim!) Use code JESSKEYS25 for 25% off. 

Last but certainly not least (although, get it quick, because it’s selling FAST!) is this linen blend swing dress! It’s the perfect shape for summer–you’ll want to wear it everywhere! I love that it’s so easy to dress up and down! How easy? I’ll show you. 😆 Sizing: Ordered my regular pre pregnancy size and it fits great! Go with your regular size or the smaller of the two. 

Here, I’ve styled it with the Loeffler Randall bow heels we already talked about above! I love the contrast of patterns that work well together (the trick? Pair a larger print, like the dress, with a smaller, busier print, like the gingham on the shoes!) 

More ways to style it: 

With sneakers and leather tote (c/o) 

The perfect outfit for the farmers market, or a cute and casual brunch! Again, we’ve already talked about how great the sneakers are, but we haven’t talked about this tote! (I just realized that all my bags in this post are from ABLE–that wasn’t planned and they aren’t sponsoring this or anything, they just make great leather stuff and I’m loving all their bags lately!)

You know I’m a huge fan of the Madewell Transport Tote, but I also adore this one–so if you’re looking for an alternative by a smaller, sustainable/ethical brand, I highly recommend this one! The leather is the kind of leather that will “break in” and get even more beautiful with time, and will continue to get even prettier once it’s beaten up a little! It’s also a little different design-wise, and the leather is more stiff, so it’s a bit more structured than the Madewell version, which I like! Use code JESSKEYS for 25% off! 

With gold Birkenstocks and Belt bag:

Last but not least, we’ve already discussed both of these essentials I’m styling our final look with, but just another example of how to stay cute, cool, and casual (AKA the summer style trifecta 😂) in this swingy summery dress! 

That’s all for now–hope this was helpful, and HAPPY GETTING DRESSED! (Isn’t it so great we can get dressed again!?)