Can I Be Comfy TWO Days In A Row—And Still Wear Real Clothes?

Yesterday’s comfy chic jogger n’ jacket outfit was a serious problem—for today. How could I even think about squeezing into anything remotely tight after that kind of comfort? Not to mention after our super salty Italian feast of a dinner. Sup, bloatation station.

I dug into the depths of the scary skirt section and brought out an old fave and a good memory- this black Enza Costa maxi I got about 8 years ago. I think I found it at a now-defunct boutique called Big Drop, but I remember knowing I had struck maxi gold! Unlike others, this skirt is soft and fitted but not too tight. And it has a sexy but not slutty slit up the side so you don’t feel frumpy. I always used to wear it during summers with tanks and sandals or heels for a flirty, beachy look. But today was no day for that. So I threw on this cute Billy! graphic tee, a label created by my uber talented college bestie Candice Pool Neistat. I knotted it in front so I wouldn’t look shlumpy.

Next up for the comfort zone? Sneaks. I thought my Adidas Stan Smiths would be a fun little punch. It was a little cool this am (before it turned into 80°) so I grabbed my blush leather jacket before heading out to grab my crack—er, I mean ice coffee.

Despite the Maje blush leather jacket everything was feeling verrry dark. So I brightened it up with green fringe H&M statement earrings and a bright Kosas lip.

This is not a look I’d normally think about rocking but this lil project is really making me look at my closet in a whole new way.

OutFit Or LeaveIT?: I am shocked the skirt still fits and is still relevant. I am not shocked that the side slit has gotten even slit-ier. I think it needs some love from the tailor before I can wear it again. Or several safety pins if I’m too lazy. Probably that one.

Lindsey Kaufman