
As most of us do, whenever the season changes I tend to feel a little rush of excitement followed immediately by panic.
Crap! What am I going to wear?!
Since having Eamon almost two years ago my size has changed and many of my staple wardrobe pieces from pre-baby no longer made me feel comfortable in my own skin. But replacing an entire closet is expensive and obviously when you add a tiny human to the family, staying within a reasonable price range is kind of key.
So I went on the hunt for some really basic dresses that would help get me through summer (and could transition nicely to those cooler months) that would help me feel cute while allowing me to be hands-free to chase around my tiny cyclone.
Things I was insistent on making sure each dress had:
– Comfort
– The ability to be dressed up or down
– Neutral colors
– POCKETTTTTTTSSSSSSSS!!!!! (This girl loves a good dress with pockets)
The following 4 dresses I happened to find all on Amazon and spent less than $90 total for them. So I felt pretty pleased with being able to accomplish what I set out to do!
4 Best Midi Dresses on Amazon
I love cotton, but I also love the things I wear to have a comfy amount of stretch. I also was determined to have each of the dresses hit me at my knee or lower and leave me feeling comfortable wearing a pair of shorts under them.
I wanted to find a few versatile shapes and styles as well so I could make them work for a variety of occasions. I decided to go with some of my closet’s staple colors so they would easily match what I already own.
One of the dresses I chose I went a little crazy with and got a purple-grey color, but other that that I chose a solid black one, a white and black striped one (sometimes adding in some patterns is a good thing!), and an army green (one of my fav colors for most seasons).
All of the following dresses come in good, staple colors though and all have felt decently made and have pockets that are actually functional and can fit my phone and chapstick in them. Which I call a win!
1. Basic Black Front-Button Dress with Pockets

I was impressed by the weight of this dress. At 95% cotton and 5% spandex, you don’t need to worry about flashing anyone in the bright summer sunshine.
While black is typically a color I try to break away from more in the summer, there are some occasions that just call for a basic black dress. And when you’ve got that sun-kissed skin (Note: I still don’t have the summer glow), black is so flattering. And super fun to pair with some cognac colored leather sandals and a cute hat (if hats are your jam).

What I really like about this dress:
I love that the dress is breathable but doesn’t feel super clingy. It has a nice shape and the pockets are the perfect size for a phone, chapstick and even a small wallet.
The hem hits right at the middle of my knees, which was a little shorter than I had hoped, but it’s a fine length for playing with E and doing daily activities.
This dress is just as perfect for park days as it is for wandering the farmers market on a Saturday morning with a cozy cardigan on top. I machine washed it on cold and line dried since it was a little snug in the shoulders to begin with (I have somewhat broad shoulders).
Here I’m wearing size XXL which I sized up to since reviews said the dress ran a little small. They had sizes S-XXL available and multiple color options including some floral patterns and a few of this same design except with long sleeves.
FOR ANY NURSING MOMMAS: This dress does not have functional buttons. I thought it did. So just be aware of that! Eamon has weaned at this point, so it isn’t a big deal for me but since I know a lot of my readers are mommas, just wanted to specify that!
2. Sleeveless Black and White Pinstripe Dress with Pockets

This dress helps me on those days where everything I’m pulling out of my closet is the same color. It’s neutral, lighter than what I typically wear, but still goes with all of my normal staples. I also liked that it was more of a pinstripe over a thicker striped pattern.
This dress doesn’t have cotton but is instead 95% polyester 5% spandex, but its nice and soft and a decent weight. I can wear black shorts or underwear under it without them being visible.

This midi dress was again not so much a midi length on me. I’m 5’7″ and it hits right at the middle of my knees. The pockets are a nice, functional size for carrying basics around. I’m not a huge fan of the chest pocket, but aside from that I like this comfort and pattern of this one.
I’m wearing a size XL here. They have S-XL available and 5 color options with a short sleeve and puffed sleeve option as well in certain colors. I’m typically a size 16 in most things and this XL is a bit snugger than I’d probably normally wear. But it’s still wearable and comfy.
3. Fitted Tie-Waist Midi Dress with Pockets in Army Green

I was the most skeptical about this more fitted style midi dress but ended up liking it the most! All of the reviews talked about how flattering the dress was and I’d have to agree. Even with my mom-belly somewhat highlighted, this dress makes me feel cute and put together.
I wasn’t sure how I’d feel about the tie waist, but I actually ended up really liking it. It isn’t a full belt, but rather is sewn into the side seams and then can go either to the front or back. I certainly think tying to the front looks best though and keeps you from feeling like you’re wearing one of the Easter dresses you wore at 8 years old.

This dress is 60% cotton, 35% polyester and 5% spandex. So it is soft and has a nice thickness to it without being too thick. I love the slightly wider neck line and the rolled sleeves.
This dress is available in sizes XS-XL and comes in 8 colors (some of those striped). This dress is pretty popular though, so you may have to keep an eye out if your size and desired color is sold out.

I love the versatility of this dress in particular. It feels grown up and can easily be worn with heels or flats. Perfect for lunch with friends or work, especially in a darker shade.
This one also hit me higher up than on the model in the photo, coming right to the middle of my knees. Which, actually, given it’s more fitted shape works better than being a true midi length.
I’m happy I decided to give this dress a try despite being a bit nervous of how the more fitted silhouette would make me feel. I think I’ll be wearing this a lot this summer!
4. Short Sleeved Grey-Purple Midi Dress with Pockets

This dress is definitely the softest of the ones I purchased and has a flattering bodice that hits at your natural waist line rather than being an empire waist. The pockets are wide but flow nicely with the pleats of the flowy skirt.
This dress is closer to a midi length on me, hitting below my knees. I also really appreciate the longer sleeve length that hits mid-bicep so the sleeves don’t roll up into your armpits as much.
I went a little bold with this one, purchasing a color I don’t often wear: a grey-ish purple that I thought would feel a bit more summery than my usual selections. I’m still not 100% about the color but everything else I’m a fan of!

What’s awesome about this particular dress is that it’s available in 20 different colors/patterns and comes in sizes XS-XXL. I’m wearing an XXL here.
Another perk of this dress is that it would make an awesome maternity dress, with plenty of room to grow plus a longer hemline that won’t leave you feeling like you’re going to give everyone a crotch shot once you’ve passed 25 weeks.

The fabric of this dress is silkier than the others since it’s 95% rayon and 5% spandex. All in all I think this one has the most versatility as far as fitting you at a variety of sizes and being able to be dressed up or down depending on the accessories you pair with it.