If you’re looking for your summer vacation packing inspo, easter dress options, or to update your 2023 wardrobe, you’ve come to the right place. Casual dresses are absolutely my favorite thing to wear. I love throwing on a simple, easy sundress and calling it a day. 

For vacation, they’re easy to pack, mix and match with different shoes or tops and elevate your overall look without having to overthink outfit pairings. While making a packing list for summer travels through Italy, Greece, Albania, and Croatia, I’ve collected a mix of dresses I either have my eye on or already own and love from Amazon – all for under $50 each! 

For style and fit reference: I’m 5’9, a size 30 (often 10/12 or L/XL), have a Soft Dramatic Kibbe body type (basically an hourglass), have a very fair complexion, and tend to dress on the modest side.

Swiss Dot A-Line Tiered Sundress

Throw this on with some Allbirds Tree Breezer Ballet Flats or Tree Lounger Slip On Sneaker while exploring the romantic city of Florence for the day, then slip on a simple sandal or sexier low-heel for the evening to wear to dinner. Two in one!

Casual Tennis Dress

Don’t let the name fool you – this dress is perfect for much more than tennis! Though you could play sports in it, it makes for an ideal travel day dress that’s as flattering as cool and comfortable. It even has pockets and a built-in bra! Ideal for a Disney park day, a walk along the beach, or, yes, tennis.

Polka Dot Ruffle Wrap Dress

A tried and true, travel approved favorite! This flattering and breezy wrap dress packs well and is the perfect addition to any summer packing list. Runs true to size and because it’s a wrap, it can be tightened or loosened as needed.

Floral V-Neck Long Sleeve Maxi Dress

Picture sightseeing through the Vatican in this cute dress – no need to worry about looking pretty, yet modest enough here! This dress is ideal for those who are cold-natured or don’t love to showcase their arms. If you’d like a little less material, this is the same dress, but with short sleeves!

Leopard Maxi Dress with Cap Sleeves

Such an easy piece to either wear to the office or a vacation happy hour on a rooftop in Spain. Dress it down with a relaxed ponytail, leather sandals, and a denim jacket, or dress it up with a heel and gold jewelry.


Jersey T-Shirt Dress

A true summer staple, I live in T-Shirt dresses and always pack them for trips. It’s so comfortable that I’ve both worn it out with sneakers and worn it to bed as pajamas. No shame in this repurposing carry-on only game! As a tip – make sure to size down. It runs large!

Boho Short Sleeve White Lace Maxi Dress

Add a nude heel for some height, or pair it with gold sandals to keep it casual. Either way, this dress is the perfect combo of relaxed yet elevated vacation vibes. And while I’m not telling you to run off to Mexico’s white sandy beaches and get married, this would be the perfect elopement dress for any boho bride.

Side Cutout Padded Shoulder Maxi Dress

Perfect when you want to feel like you’re wearing a t-shirt dress but want just a little bit of added sexiness. This comes in so many great colors it’s hard to choose just one!

Square Neck A Line Maxi Dress

This dress is incredibly comfortable and easy to wear. Throw it on for date night or a boat trip, or to pair a casual denim jacket with it and wear it to church. I wore this one on our boat tour from Positano around the Amalfi Coast last year, and it was perfect!

Sleeveless Fitted Cotton Tank Dress with Ruching

I love this dress so much that I have it in both navy and black. Toss it on with sandals, and you’re ready to run errands or add a low block heel and a slouchy blazer, and you’re ready for work. Also, as a thick-thighed lady, I can attest that you can easily wear bike shorts underneath, and they’ll never show.

One Shoulder Casual Tiered Maxi Dress

This dress screams summer date night, picture-perfect wedding guest, and girls’ trip. It runs a little small, so I’d recommend sizing down. If you’d like one similar that’s a little more flirty and fun, this one could be perfect as well!

Short Sleeve High Slit Maxi Dress

I’m totally taking this dress, simple jewelry, and a pair of espadrille wedges on vacation with me this summer. This material packs well as it doesn’t easily wrinkle, and this dress keeps those shoulders covered after seeing too much sun on the beach. As a bonus, it comes in many colors and long-sleeve options.