If you are looking for a trendy and stylish, yet amazingly comfortable outfit, then you’re going to love my favorite comfy casual outfit! It is so simple, but I receive SO many compliments when I wear it. Wondering what it is? Black leggings, a white sweatshirt with a black pleather puffer vest, tall white socks, and Chuck Taylor All-Stars – or Chucks as we called them growing up.

Black leggings, white sweatshirt, black vest, white socks with White Chucks

I know, so basic, but seriously, this comfy outfit is perfect for all ages! I wear it traveling, on lounging days, out for errands. And I always get compliments for being so put together – when I’m wearing it on my laziest days!

Stylish comfy outfit with mid-top Air Jordans

And changing up the shoes totally changes the look of the outfit! In the photo above I paired it with some mid-top red and black Air Jordans for a more sporty look. I’ve even changed up the black leggings for a pair of blue ones with the Chucks and I love that outfit just as much. There’s just something about looking good in comfy clothes, am I right?

This outfit is perfect for Fall, Winter, and Spring and I’ll be sad when I put it away for Summer – though I am so looking forward to the ease of wearing summer dresses!

Black leggings, white sweatshirt, black vest, white socks with White Chucks

Ready to pull the trigger and add this comfy staple to your wardrobe? All of these pieces can be found on Amazon! We love an easy purchase, delivered straight to your door, with free returns!

Head to my Amazon Page to get the whole look today!

Everyday Comfortable Outfit

I may earn a small commission if you purchase any of the products that I recommend.

The Air Jordan 1’s that I’m wearing are no longer available, but a very similar Black and Red Air Jordan 1 is available. And I’m sure you can find plenty of other options just by searching!