This is the year we really learn to love dressing for ourselves, is it not? As much as I miss picking outfits for social occasions, I’ve come to intimately love what’s in my closet AND have officially given up wearing things that aren’t both comfortable and flattering. It could be my age, the changes in my body, or the COVID-15 (hello, comfort food) but I love the freedom that comes with saying NO to worrying about my pant size and YES to what feels right on my body on any given day.

Here’s a little snippet of what a week of getting dressed looks like for me right now.

Monday – Pajama Top and Dark Jeans

This could not possibly be more inspired by this stay-at-home lifestyle. A bright striped pajama top and simple dark (stretchy) jeans was the ticket to starting my Monday out feeling put together while totally embracing a “what a weird year it’s been” mentality. I think I’ll take this outfit with me into “normal” life, whatever that looks like. A fitting choice for any Monday!!

Product Sources: Thrifted pajama top, Thrifted Levi’s jeans, Birkenstocks sandals

Tuesday – Pajama Bottoms and a Sweatshirt

The kids were up late and I woke up bloated and feeling a little blue. Cute pajama bottoms from Mille are a nice pick-me-up and look cute and flattering enough to get away with as an “outfit” while also fully embracing the fact that some days we just can do the bare minimum. Tuesdays, why are you so terrible sometimes!? 

Product Sources : Mille pajama set, Gildan sweatshirt

Wednesday – Polka Dot Dress

All dressed up with not a lot to do! I have been really into grabbing statement dresses on days when I’m feeling like I need to switch things up. I think the hardest thing about staying at home more is feeling like each day is a little different, and changing up your outfit rotation is a way to shake things up a bit. I’m feeling on top of it and organized today—maybe I found some extra confidence stowed away in the massive sleeves of this dress. 

Product Sources: Target dress

Thursday – White Jeans and a Blouse

I didn’t put on jeans for a few weeks this summer and when I slide on these high waisted wide leg trousers from Madewell, I remembered how much I love wearing white jeans and flowy blouses in the summer. This top is from Mille and the pattern and oversized sleeves make me smile. It’s flattering on EVERYONE. Now if I could only find the motivation to wash my hair. 

Product Sources: Mille top (gifted), Madewell pants (gifted)

Friday – Oxford Top and Shorts

August told me I looked like a boy and I said, “THANKS IT’S MY FRIDAY LOOK.” I got a blank stare and then an, “Ok mom!” I thrifted both of these pieces and they’re kind of ’90s waspy staples: Ralph Lauren oxford, Lee pleated khakis, slide on birks. It’s comfy and relaxed and still a look, as the kids say these days. 

Product Sources: All thrifted

Saturday – White Dress

This is my go-to look for the summer. I have four different white dresses in rotation and it’s basically like wearing pajamas that are appropriate for both napping on the couch and having a cocktail, which is what today consists of. Weekends shall remain weekends, I say!

Product Sources: H&M dress (sold out), similar here

Sunday – Cardigan and Chinos

Sunday is my catch up day for opening mail, paying bills, and doing some writing. I also love to sit outside with the paper and do the weekly crossword puzzle. Considering I was in my “fancy pajamas” dress all day yesterday, pants that are comfortable but look put together fit the bill. I’ve kept this Maria Stanley cardigan in my office for when I get chilly and it’s got the best shape with the cutest neckline and buttons. I should probably hit the coffee stains on my shirt with a tide pen. Why is it that whenever I wear white I spill coffee on myself IMMEDIATELY? 

Product Sources: Maria Stanley cardigan (gifted), Thrifted chinos, & Other Stories tee

How has getting dressed changed for you during this wild year? Anything you’re feeling inspired by? Please share in the comments below!

Kate Arends

Kate is the founder of Wit & Delight. She is currently learning how to play tennis and is forever testing the boundaries of her creative muscle. Follow her on Instagram at @witanddelight_.