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Affordable Resort/Vacation And Poolside Flowy Dresses (With Sleeves)

There are things to splurge on – things with structure or the perfect tailoring, and then I feel like there are some things that by nature can be more affordable – where they are meant to be looser and therefore maybe could be constructed with less detail. That was my thought/hope at least. So I went shopping to see if we could find the non-$300 flowy vacation dresses that would be good for poolside or a resort and since I like sleeves on me all of these will indeed have sleeves. And to make them more fun, all of them have patterns or prints. Very throw and go so you don’t even think about it, you know you’ll look cute:)

Dress | Purse | Sandals

This one is the splurgiest from Anthropologie, but the fabric is soft and super airy, doesn’t wrinkle easily and the pattern makes it super easy to wear. The sleeves bell out a bit, and V is more low cut also I’m going to stitch it a bit to keep it from showing too much bra (which I don’t think is a problem, but I don’t love it). But that’s how much I liked the dress. It does run a little big, FYI.

Sunglasses | Dress | Bag | Platform Sandals

This one is decidedly less “me” but my goodness H&M had so many fun options. This is definitely a little bolder and goes slightly glam, but for dinners on vacations, I feel like it’s soooo easy to wear and still looks dressy.

Bandana (similar) | Sunglasses | Dress | Belt Bag | Sandals

I LOVED this one. It’s a total kaftan and super loose and flowy. The fabric has rayon in it so it flows and drapes really easily/well. It’s hard to see the shape of it but it’s just a long, loose, flowy dress that you could wear with flip-flops or dress it up like I did with a cute bandana and sandals. I will wear this one a ton when I want to feel “resort vibes”.

Hat | Sunglasses | Dress | Bag | Platform Heels

This dress (also from H&M) had such a good floral print. Also, it definitely has some fun detailing. I’m not sure it was the best cut for my shape but I still thought it was so cute.

Hat | Sunglasses | Dress | Purse | Platform Sandals

This was my attempt to see if I could find any affordable versions of the Daughters of India dresses (which I tried and are soooo pretty but hit my boobs in the wrong place). I bought a few on Amazon to test out and this is the one that I kept. The colors and prints are not as good as they could be, but it felt so fun, drapes so easily and for $32 I had to admit it was a decent version. Very easy to wear and fun.

I actually photographed so many dresses on this day I have another post coming next week for more daytime summer dresses (also printed, patterned, and with sleeves but slightly more dressy). I was clearly on the hunt and went to all the usual suspects (Target, Madewell, Anthro, Old Navy, Gap, Free People). I was surprised at how hard it was to find what I was looking for until I went to H&M and then a couple of higher end boutiques. I hope my sleuthing helps:)

*Photos by Kaitlin Green

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29 days ago

Thank you for this! Waiting to hear if the green HM dress comes back in my size. But then found a longer dress in the same fabric as the HM one you don’t like so much, so bought that one! Not long sleeve, but long length to cover the legs to make it easy to wear. Thank you!

Amy B
29 days ago

I’d love a post on how you (Emily) dress your body type! I’m also on the shorter side and quite busty, and when I wear loose cuts like this it adds 20lbs to my frame. How do you still look proportionate in looser styles?!?! I’m desperate to know, because structured dresses during a Portland summer are not my favorite 😂

28 days ago

What are the pavers you used around the Soake pool?

27 days ago
Reply to  Elissa

“Our tumbled bluestone hardscape conducts so much heat that we can’t sit or walk on it on really hot days (in the afternoon). This isn’t Soake’s product, this is what we chose to work with our blue flagstone pathways. It’s VERY pretty, but y’all it holds so much heat. This is why we have three umbrellas to create shade not only for the kids in the pool, but so they can sit around it”

28 days ago

These are so cute! Fwiw, this is the category that I have the best luck thrifting lately. Maybe because the sizes don’t have to be exact or maybe people buy them for vacation and then donate them, who knows. Like you said, they’re easy to alter too (straps, length, neckline, etc), so worth a look for those who have the time/bandwidth.

27 days ago

It’s not just you, the fit of the Daughters of India dress is so off. I had to size up two sizes to get it to fit like the model. Weird!