Interesting Ways To Wear Pajama Pants

Easy to wear, impossible to f*ck up.

If we’re talking about weekend wear, or everyday wear, we have to talk about pajama-style pants. Not literal PJs, I mean elastic or drawstring waist trousers that are kind of unstructured and soft. And this is a type of pant that basically works at all ages and most body types - they’re comfortable and forgiving, but if you treat them right (keep them free of stains and not run through the dryer eight million times) they can look really sharp. These are favorites of My Fancy Mom, because they’re not too hot in the summer (so they can sub in for shorts), they’re comfortable, and they don’t look old and dowdy and fusty. I also love them. To me, they can be super casual, perfect playground clothes, or, if you put in a little effort they can look insanely stylish. They’re not an obvious choice for something more polished or formal, so when you do it, it looks very cool.

I have a few pairs, but for today, I’m working with three favorites that all kind of serve different purposes. Here’s how to style them.

CROPPED AND STRUCTURED AND SOLID

Madewell sweatshirt, $89 ; Leset pants, $280 ; Co clutch, $775 ; A.Emery flip flops, $170

These pants are by Leset, and I LOVE the crazy vivid blue. This is one of my favorite colors in the world, and I think these pants are gorgeous. I’ve machine washed (but not dried) these, and they still look great. I’m wearing a Medium, but I kind of wish I had a smaller size. I like them with a super bright sweatshirt like this genius one from Madewell. The sweatshirt has some structure, which I like with the structure of the pants. This is so easy to throw on, and it looks killer - a win for every day or weekends. The clutch makes it more formal, but obviously you can wear any kind of bag here.

Everything’s the same as before, except these EXCEPTIONAL Dries van Noten wedges, $695

You can add a pair of interesting heels and do literally nothing else for something great to wear out to dinner with your friends.

But I get it is A LOT of color for some. For me, the best way to wear color is to meet it with more color, OR….wear two similar hues…like this:

Comme Si shirt (I wear size L), $275 ; Leset pants, $280 ; Kule bag, $158 ; Gucci clogs, these are better!

This is, top to bottom, the outfit I wore this Sunday out with my in-laws and my family for lunch at République. This is the perfect weekend outfit IMO. The blue of the Comme Si shirt (Grecian Blue) is just close enough to the pants to look good together, but not so close that they look like a matching set. The little Kule bag is a nice silly happy matching addition.

Same shirt and pants as before; Indress feather brooch; Emme Parsons heels, $565

And of course, I love it with a feather puff and some heels for something fancier. I’d wear this to a party (if I went to parties…).

Dries blazer, this is similar ; Leset pants, $280 ; Co clutch, $775 ; Jamie Haller flats, she does’t make silver anymore, but these are still incredible shoes.

A blazer also works here for running around - this one is especially good with the pants because it’s cropped and boxy - a longer one would feel too overwhelming with these pants. This blazer is Dries, and I can’t find it online, but here’s a similar one in navy. I also prefer it closed and worn as a top instead of with a tee or tank underneath. This makes it feel a little more polished and styled, whereas wearing it with a tank or tee feels….businessy? I can’t explain it.

Everything the same as before, plus Khaite sandals, $960

And they’re great too with a little bit of a heel and a little bit more color. These Khaite beaded sandals are the greatest summer shoe - the beads remind me of summer camp, but they’re also gorgeously minimal, and the heel hight is very comfortable!