Friday Favorites: 9 Casual Comfortable Summer Outfits

Looking for something to wear this summer that’s cute but casual? These comfortable summer outfits from Amazon are all that, and affordable too!

Summer is here and it’s time to find some cute outfits that are great for day-to-day wear.

Last spring I shared some pretty and affordable tops from Amazon that are great for going out and about, going to conferences, or for date nights.

But let’s get honest here.

The vast majority of my life is spent working at home.

It’s tempting to stay in my pajamas, but I find I’m way more efficient if I take the time to get dressed.

My husband works from home too, so I wanted to find some outfits that are comfortable but kind of cute too!

I can’t wait to share the nine versatile outfits I put together!

Collage of Anne from Simply2Moms wearing 9 different casual summer outfits.

Before we get started, I want to share my stats.

I’m 5’1″ and 138ish pounds.

Since going through menopause, I’ve been dealing with some stubborn weight that’s settling around my midsection.

I wear a 36 D bra so shirts don’t ever fit me the way they look on the models.

Some of the things I picked out were homeruns, and a few need some size adjustments.

I’m also sharing some of my favorite summer accessories at the end of this post.

Hopefully my reviews can help you find some fun additions to your summer wardrobe too!

Table Of Contents

Waffle Knit Henley Shirt with Tied Bottom with Cropped Jeans
V-Neck Tunic with Ruched Sleeves with Straight Leg Crop Jeans
V-Neck Pocket Tee with Contrasting Trim with White Denim Shorts
V-Neck Tee with Striped Sleeves with White Denim Shorts
Split V-neck Waffle Knit Tee with White Denim Shorts
V Neck Tee with Twisted Knot Bottom with WHBM Pret-a-Pedi Crop Pants
Smocked Eyelet Top with WHBM Pret-a-Pedi Crop Pants
Tie Front Ruffled Crop Top with Straight Leg Crop Jeans
Sleeveless Maxi Dress with Side Slit with Distressed Denim Crop Jacket
My Favorite Summer Accessories
Resources and Shopping Links
Pin it to Remember it:

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Waffle Knit Henley Shirt with Tied Bottom with Cropped Jeans

Anne from Simply2Moms wearing a short sleeved black waffle weave shirt that buttons in the front with a tie at the bottom.

Let’s get this started with one of my favorite new tops!

This super soft Waffle Knit Henley Shirt with a Tied Bottom is really comfortable, and I love that the buttons dress it up a bit more than a regular T-shirt.

The sleeves are long enough to cover my arms that aren’t looking quite as toned as they used to look.

It’s casual enough that I can wear it around the house when I’m working, but it’s got a little style so I feel a little cute for my hubby who also works from home.

It comes in 14 other solid colors and 7 patterns, so I might get one in another color too since it washes really well.

I’m wearing it with my favorite Kut from the Kloth Straight Leg Crop Jeans. They’re a little pricier than some jeans, but they’re so comfortable and fit so nicely that they’re worth it.

V-Neck Tunic with Ruched Sleeves with Straight Leg Crop Jeans

Anne from Simply2Moms wearing a short sleeved V neck tshirt and jeans with running shoes..

Anne from Simply2Moms wearing a short sleeved V neck tshirt and jeans dressed up with a necklace and sandals.

It’s hard to see in these pictures, but this V-Neck Top has pleated detailing on the sleeves that make it just a little bit cuter than a regular T-shirt.

It’s casual enough to wear with running shoes, or you can pair it with some cute Black Wedge Sandals and a necklace for lunch out with friends or a casual date night.

The material is really soft and has some stretch to it, and it’s considered a tunic so it’s long enough to cover the booty if you want to pair it with leggings instead of these fantastic Straight Leg Crop Jeans.

You can find this shirt in 8 other colors, and there’s also a slightly different neckline with the pleated sleaves in 17 colors and 10 patterns.

V-Neck Pocket Tee with Contrasting Trim with White Denim Shorts

Anne from Simply2Moms wearing a black short sleeve tshirt with contrast details around the neckline and sleeves.

I’m a little disappointed iwith this V-Neck Pocket Tee with Contrasting Trim.

It’s described as loose fitting and “true to size” and it’s extremely loose on the model, so I ordered a small.

Annnndddddd, it’s not even remotely loose.

It is super soft, and I really like the contrasting trim so I think I’m going to order a medium and a large and see if it works in a larger size.

It also comes in 15 other color combinations so maybe I’ll try something different?

As I’m getting older, the skin on my legs is starting to look a little crepey so I don’t wear shorts as often. There are just a few styles that I still like, and these White Levi’s Shorts are my favorites.

I like that they’ve got a 5-inch inseam so they’re a little longer, but not too long. They’ve also got a little bit of stretch to them so they’re really comfortable.

V-Neck Tee with Striped Sleeves with White Denim Shorts

Anne from Simply2Moms wearing a black round neck Tshirt with white stripes on the sleeves.

I know, I know! It’s black. Apparently I was channeling my inner AnnMarie when I was ordering…

In keeping with my casual selections, this V-Neck Tee with Striped Sleeves is one of my favorites. Since it’s available in 36 other color combinations, I may order a few more after I’ve washed it a few times to make sure it doesn’t pill or shrink.

I ordered a Small and it fits really well as long as it doesn’t shrink… LOL!

I like that the sleeves are a little longer, and the shirt is too, but it’s not so long that I feel like I need to tuck it in.

It’s a little fitted, but the super soft material doesn’t cling to my back fat so there’s that…

Once again, I’ve paired it with my favorite White Levi’s Shorts.

Split V-neck Waffle Knit Tee with White Denim Shorts

Anne from Simply2Moms wearing an olive green split V neck tee shirt and white shorts.

Finally! A shirt that isn’t black!

I love just about everything about this Split V-neck Waffle Knit Tee! It’s soft, it fits well, and it comes in 15 colors in either long or short sleeves. I ordered a small.

The split V-neck style is flattering and I like that the length hits in just the right place so that it can be either left out or tucked.

I have another shirt in this same fabric and it washes really well and doesn’t shirnk, so I may get another color (or two)!

It pairs perfectly with my White Levi’s Shorts or jeans.

These Wedge Sandals with Ankle Straps are probably my favorite sandle this year.

They’re really comfortable, they add a few inches to my height, and they’re so cute!

V Neck Tee with Twisted Knot Bottom with WHBM Pret-a-Pedi Crop Pants

Anne from Simply2Moms wearing a light blue short sleeved T-shirt with white pants.

I’m really happy with this V Neck Tee with a Twisted Knot Bottom!

In the shopping photos, it looks like it’s really long, but it doesn’t come down nearly as far on me. I’m guessing it’s because the models are both very slim and flat chested…

I ordered a small and I like that it falls just below my waist, but if you’re busty and you want a longer fit more like what’s shown on the model, you may want to size up.

These WHBM Pret-a-Pedi Crop Pants are my favorite summer pants because they’re really comfortable and they fit really well.

They were a splurge, but I don’t mind spending a little more on jeans and pants since the fit is so important. Plus, bottoms tend to stay in style way longer than tops.

You can wear them with flats, Birkenstocks, or these fun Brown Wedge Sandals.

Smocked Eyelet Top with WHBM Pret-a-Pedi Crop Pants

Anne from Simply2Moms wearing a red smocked eyelet short sleeved shirt with white pants.

Most of the tops I ordered fall in the super casual and comfy category.

This Smocked Eyelet Top is definitely comfy, but it’s a little less casual.

After all, sometimes AnnMarie and I are gonna go out to lunch this summer, right?!

It’s very roomy, and I ordered it in a small.

You can find it in 10 different colors, but I’m not sure that I’d rely on the website for how they’ll actually look. This shirt looked more maroon on the model, but it’s definitely more red.

There’s plenty of room for the girls and the buttons don’t gape at all, so that’s a win!

I paired it with my favorite WHBM Pret-a-Pedi Crop Pants here, but it’s cute with jeans too.

Tie Front Ruffled Crop Top with Straight Leg Crop Jeans

Anne from Simply2Moms wearing a tie front ruffled crop shirt with jeans.

This Tie Front Ruffled Crop Top is another top that’s a little dressier than my other choices, but I think I really like it!

I wasn’t sure if it would be too short, but I don’t think it is, as long as I’m wearing mid-rise or high-rise pants.

I ordered it in a Medium, but I’m considering exchanging it for a Large so that it’s a little roomier through the bust.

The ties can be adjusted to tie them a bit tighter so there’s no gaping in the cleavage, but that makes it a little tighter than I like.

The neckline is more revealing than I’m comfortable with anymore, so I like putting this Bandeau Bralette Top underneath.

I really like that the ruffle is very forgiving of my midriff area.

You can find it in 18 different colors, so there’s something for everyone. I wish it came in maroon or orange because it would be super fun for tailgating season!

I’ve paired it with my absolute favorite Kut from the Kloth Straight Leg Crop Jeans that I wear pretty much all the time.