I really shopped high and low for this post, desperate to find more nice-looking, comfortable, throw-and-go summer dresses that feel easy to dress up and down (you know, just the “comfortable and pretty” combo that is so elusive). Most of the common retailers didn’t have any fun prints or patterns (looking at you Madewell, J.Crew, Gap, and Target) but I was able to find some that I really love and I’ve been having fun wearing them.

Hat (similar) | Dress | Bag | Platform Heels

Splurge: This is Trovata, Birds of Paradise and yes, their dresses are on the splurgier side. I bought this for a speaking engagement where I knew I’d be sitting the whole time (thus not wanting to wear a tiny dress which I’ve done in the past and it’s A LOT OF THIGH). The color and sleeves are so cute, the print is busy and playful, it has pockets, is very flowy, and while it’s thin (and so drapey), it is colorful enough not to be too see-through. The shoes are solid and so comfortable for being so high. They aren’t “all day around town” comfort like these ones are, but they are dressier and are still a 7 on the comfort scale. The bag is from Madewell (and the hat I think is an old Madewell collab I’ve had forever).

Denim Blazer (similar and affordable!) | Sunglasses | Dress | Bag | Mules

H&M really got the “fun, affordable, and comfortable” dress brief this year. This dress, especially, when paired with that denim blazer is so fun, graphic, and cute. It’s a great Friday afternoon into happy hour vibe that still feels professional but shows some personality. Oversized sunnies from H&M (so good), shoes are Nisolo and again the bag is Madewell (and coming very in handy – the perfect size for laptops and other stuff).

Hat (similar) | Sunglasses | Dress ( + similar) | Belt Bag | Sandals

Ugh, I’m not selling this dress as good as it is. It’s so bright/bold and has a drop waist that keeps it casual. It drapes so easily and is the perfect picnic dress because you don’t constantly have to adjust like you need to with shorts or shorter dresses. I’ve found myself wearing this frequently around town or at kids’ sports before it gets crazy hot.

Dress | Belt Bag | Sandals

Ok now this one didn’t end up working out for me but I wanted to show it to you. I love so much of Doen (just bought this shirt and this shirt, both incredible) but this dress is too thin and short for me (just feels like an expensive nightgown). I think it just needs to fall better and likely would on someone with smaller love pillows. Still cute, but not a hit for me. The sandals are basically an elevated Teva, with an almost snakeskin print in that nude color that I obviously like. Don’t look too closely – I haven’t had a pedicure since March, sooo…

Sunglasses | Dress | Bag | Platform Heels

This is another one that I put on and was a fast “yes”. It’s so fun to wear, has an extremely full skirt (so a ton of movement) great pockets, flutter sleeves, and a deep V. If you are long torsoe’d this will be too short because I have a short torso and it’s almost too short for me. But I’ve worn this to kids’ sports games with sandals and a ton around town when I want to look like I care but also be super comfortable (especially before the weather got hot). I bought at a local shop (shout out to Adorn in Lake Owego) and I’ll be following this brand from now on.

Sunglasses | Dress | Bag ( + similar) | Platform Heels

Another great “work to happy hour” vibe. Mille is splurgier, too, but always has great shapes of collars and sleeves and so many prints. I ended up returning this one because it was a lot of volume for my frame (and it was expensive), but if cost weren’t a factor I would have kept it and dressed it down with sandals or threw on a blazer to tame the volume. (Hey Mille, it would be awesome to make this in a drapier fabric!). Big round glasses from H&M (and I LOVE wearing them, they look so expensive and the huge frames make it easy to see).

Hat | Dress (similar) | Platform Sandals

Another one that isn’t necessarily very “me” but it’s so cute, affordable, and easy to wear for the summer months. Brunch, shopping, city walking…I have too many clothes right now without an office job to go to, but again with a cute blazer/jacket, it could easily go from work to happy hour. You can’t see the slides that well but they are really cute (leather on top and jute on the sides). Very comfortable.

Sunglasses (similar) | Dress | Bag ( + similar) | Platform Sandals

I was really drawn to this one because of the cute print (obviously) and the fun sleeves. Definitely an easy weekend dress (or work if you work in a more casual environment). Those are the platform sandals (Sorels!) that I’ve been wearing nonstop and that cute bag is from H&M (I love the multi-texture/finish of the raffia and faux leather).

If you missed last week’s poolside, resort, and vacation dresses post go check it out. I’m officially fully stocked on dresses for the summer LOL.

*Photos by Kaitlin Green