Seven Cute Comfy Outfits For Summer

T-shirt dresses, tee dresses, or oversized t shirt dresses, whatever you call them, they’re the best. If you haven’t caught on by now, my closet is filled to the brim with dresses like these because they’re so darn comfortable! They’re also so versatile. They can be worn on lazy summer days when you’re hanging out at home or running errands. Or you can dress it up and wear it as a date night dress (like I did with this striped number).

For these dresses, I mentioned in earlier posts, but I love styling them with slide sandals. If I’m going to be doing a lot of running around though, I might pair them with my low top converse. If I know the day is going to be chilly, I’ll also make sure to grab a jean jacket. It’s a perfect touch to any tee dress.

Yes, I felt the need to specify NON-JEAN shorts. Why? Well, yes, I could go the route of jean shorts, but that just seems so easy. I have nothing against jean shorts, I love them. But you haven’t felt a truly cute comfortable summer outfit until you’ve worn a pair of cute cotton shorts with your outfit. They’re so much more comfortable and allow you to play around with your outfit a little bit more.

I loved this pair (though it’s a few years old), because the high waist makes it a little more dressed up than any old pair of shorts. So even when I paired it with just a plain white tee and sneakers, the outfit looked classier than it would have if you had subbed out these shorts for jean shorts. Isn’t it crazy how just one piece of the outfit can make a world of difference?

After a whole post on long dresses, you think I would be sick of maxi dress talk, right? Wrong! I love these long dresses too much. How can you get sick of a dress that can go from a nap to dinner?

Since I already did a whole post about the different types of maxi dresses and how you can dress them up or down, I don’t think we need to go into detail about that again.

But I will leave you with this: if you want the comfiest maxi dress possible: look for a jersey material. It won’t be the best at keeping it’s shape, but it will be the MOST comfortable option.

Is there anything more summery than a white tank top? Nope! And lucky for you, white tank tops come in all shapes and sizes.

Personally, I prefer the spaghetti strap or halter versions the most, but honestly go for whatever makes you the happiest. The best thing about these tanks is that they’ll go great with just about everything, so you really can’t lose.

My favorite combination is the white tank with a skirt (as you can see here), but really, go with whatever makes you happy and makes the occasion.

In terms of fabric, that will really change based on how fancy you want to go. If you wear a basic cotton, you’re going to look more casual, no matter what. However, if you go for the more polyester, rayon, silk look, you’ll look a little more dressed up. With my look on the left, I went for a cotton skirt, with a faux silk top, for a dressed up, but still casual look. It was the perfect daytime date look. In fact, this was what I wore on my first date with my fiancé! (He is getting way too many shout outs on this post.)

Including joggers here might be a little controversial, but I think that’s because people may have forgotten that pre-pandemic, we were all wearing a nicer version of these to work.

Yes, really. We all had joggers in a nice looking material and it was work appropriate. No sweatpants here.

So how did I style them for work? It was super easy!

I would pair them with a nice (ie not cotton) tank or blouse and a Jackie O style cardigan. Then I would wear a pair of cute flats. The goal was to look completely put together. If I looked slightly sloppy wearing joggers then you went too close to the sweatpants zone, which was not what I wanted.

Also, this was just me, but I tried to keep my work joggers to just a neutral navy or black. The simpler the better, in this case.

Don’t worry, I would never forget about denim jackets. They’re the perfect completer item for all cute comfy outfits for a casual summer.

Why?

Well, first, they go with just about EVERY outfit! Second, they actually can help to keep you fairly warm if it gets chilly (which it can at night during the summer). So depending on where you are, it’s pretty nice to have a jean jacket on hand if you’re going to be outside at night.

What I also love about jean jackets is that there isn’t a standard “perfect shade” for a jean jacket. I have one in white, one in dark blue (like the picture on the left), and a light blue one. Each one feels so different and perfect for different reasons. I also don’t know why, but the white one even just seems a little dressier than the ones. It makes zero sense since it’s still denim, but whatever. The white one is great to pair with maxi dresses, so I’ll take it.

Cute skirts have already come up in so many pictures, I bet you’re surprised it took me so long to talk about them (and if not, whatever, humor me). If you don’t have at least two cute skirts in your wardrobe, fix that stat.

Cute skirts are a must for summer. They’re great for date night, meeting up with friends, or just being comfortable outside. Like any great dress, skirts provide ventilation that your body needs, but they have the added bonus of letting you pair them with any of your tops for a number of cute outfit ideas.

It doesn’t matter whether your skirts are mini or maxis, either way, they’re a must have for any summer wardrobe.