10 Casual Summer Dresses from Amazon under $100

The most-asked question in this week’s “What are you shopping for” question box on my Instagram was casual summer dresses that are affordable, and this post was already on my mind, so it was perfect timing! Since I’ve had such great luck with Amazon Fashion this year, I made a goal to fill this post entirely with Amazon dresses.

My shopping philosophy is a mix of highs and lows. I love to splurge on a summer dress from Tuckernuck when I know I’ll wear it many times, but I also know that a simple dress can be just as great from Amazon. I stuck to the casual theme since I personally don’t have anywhere to wear a more “fun” summer dress in this stage of life, and I already have athleisure dresses linked in this post. I need things I can wear everyday to chase a toddler, and if they can be dressed up with heels for church, I’m happy.

Okay, let’s dive in. I’ve included a few dresses you’ve seen before because I keep wearing them!

Casual Summer Dresses

1. Britt Tiered Maxi Tent Dress

I actually own this maxi dress in the solid orange colorway and the striped orange version. And I’m also eyeing the yellow stripes. The fit is perfect (not too tight under your arms), and the length hits right above my sandals (I’m 5’1″). Best part? It has pockets!! If the straps don’t stay on your shoulders well, you can cross the straps before you put it on! (An instagram follower gave me that tip – brilliant.) This is the strapless bra I wear with it.

2. Black T-Shirt Dress

You can’t beat a comfortable t-shirt dress for summer. It’s one of the most versatile things in my closet! They’re easy to wear with any bra, work perfectly with sneakers or sandals, and can be styled multiple ways: with sneakers and a ball cap, sandals and a sweater over your shoulders, with a denim jacket on top, or even with some casual heels for a lunch with friends.

This Amazon Essentials t-shirt dress is under $25 and has almost 11K positive reviews. I’d get the black (unless you have a dog that sheds), since it’s going to be the most flattering. I ordered an XS it’s slightly long on me, but I honestly love the length! If you’re a few inches taller than me (I’m 5’1″), then this will be PERFECT. The sleeve length hits at a flattering spot on the arm too.

3. Smocked Fluttersleeve Maxi Dress

I’m always drawn to casual maxi dresses because they are SO easy to wear with a toddler around. I know that may sound strange because most people associate a maxi dress with something more dressy, but I’ve found that a maxi dress (as long as it has a casual fabric) is super easy to wear chasing Thomas. I never overthink if it’s too short or showing my biker shorts (that I wear under all short dresses), and if it’s from Amazon, I never have to stress too much about ruining it since it’s affordable. This Fluttersleeve Maxi is a great option for nursing mamas as well because of the smocking. You can just pull the straps down to nurse.

I got this in a red color since I thought it might be a good 4th of July option, but it comes in over 40 colors! I have a size XS.

4. Summer Gauze Bell Sleeve Mini Dress

I’m so glad I scooped this mini dress up because the sizes are flying. I ordered the yellow in a size XS. I’m loving bright colors this summer, and I figured this yellow would be fun to wear as a coverup to our pool and the beach, or to style on super hot summer days with sandals. The gauze material is perfect for hot weather.

5. Pink and Orange Floral Maxi Dress

I was immediately drawn to these colors when I saw them. The pink and orange scream summer, and the maxi length is my recent favorite. I also love that it has sleeves since the majority of my maxi dresses are sleeveless. You could easily dress this up for church or dinner!

6. Navy Midi Dress Smocked Dress

I saw another influencer share this navy midi dress on LTK and could not believe it was from Amazon. I immediately ordered it since it takes a while to ship. I’m always annoyed when something doesn’t have prime shipping, but the blogger looked so cute in it that I figured it is worth the wait.

Update: It just arrived and it’s GOOD.

7. The Drop Jaya Smocked Bodice Chiffon Maxi

This is the other dress that I wanted to re-share (I know I’ve linked it a few times already) because I’ve been wearing it SO often. The quality is so good and the colors feel so pretty for summer. I have an XS in the pink floral and it fits true to size.  The only bummer is no pockets.

8. Cotton Stripe A Line Midi Dress with Pockets

I got this tie shoulder striped dress a few months ago for my Easter Dresses round-up and keep meaning to re-share it as an idea for the 4th of July. It has a slightly longer smocked bodice which is just SO flattering. I wear it with flat sandals most often, and I also highly recommend this one for nursing mamas.

9. Collared Shirt Dress

I haven’t ordered this sleeveless shirt dress yet but I hear great things. I was slightly nervous about the super wide arm holes, since I thought it might look too big, but the other people who’ve been wearing it look SO cute in it. It’s a little bit oversized, which is fun.

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