Cheryl Shops

Spotify's year-in-review posts came out last week, so you know what that means: time for the year-end wrap ups! I'm changing things up a bit this time; it's always hard to pick a favorite outfit of the year, so I thought I'd do something different and pick 10. This was actually harder to do than I expected; turns out I liked a lot of what I featured here (although I did have some duds, TBH). Still, it's funny to see some trends emerge: I still love neutrals, but I did try a little (soft) color here and there, and clearly I have some favorite accessories! In no particular order, here are my 10 favorite outfits of 2021—tell me your favorites in the comments below!

What to wear with a designer hoodie 

I debated buying this hoodie for months—I'm usually not one for logos, and this was admittedly an exorbitant amount of money to spend on a sweatshirt. Oh, and 2020 seemed like the year of the hoodie, but here we are, still working from home and dealing with the pandemic. That said, I love how this look came together, especially with the pop of red from my loafers (which are ridiculously comfortable). 

What to wear in February

I tend to go for a lot of black and gray in winter, so I loved how light and bright yet still neutral this look felt. Pink and camel is a highly underrated color combination and one that I definitely need to wear more in 2022. 

An honest review of Sarah Flint shoes

I built this look around the shoes, which reminded me of a style my mom wore to work in the '80s. The result was something very classic and layered, and it's composed of some of my favorite wardrobe workhorses, including my Everlane alpaca sweater and Spanx perfect black pants. I think it's proof that the classics are classic for a reason. 

The first pair of shorts I bought in 20 years

I think this is literally the first time I've worn shorts on this blog, and I was kind of proud of myself for pulling them off. I had been seeing a lot of blazers-and-shorts on Instagram and thankfully Chicago gave me warm enough weather to re-create that combination, with my own twist, Isabel Marant belt included.

What to wear in June

This post featured both a rare sighting of my bare arms (they're obviously not my favorite body part) and a very colorful (for me) dress. I had been wanting to buy this dress for awhile—Ganni puts out several different colors every year—and glad I waited for this one, because looking at it makes me super happy. I was also feeling my summery accessories in this post.

What to wear with a tie-dye sweater

Speaking of accessories I was feeling, clearly the straw bag here was a favorite, and I still love the fuzzy shoes I'm wearing here. More importantly, these are my "pandemic jeans"—they're so soft and stretchy, they almost feel like sweatpants (almost). I also love this tie-dye cardigan, which was a birthday purchase from Madewell.

What to wear in August

I discovered COS's barrel cut jeans in Chicago, where I bought these; they're really comfy yet look so fashion-y, in a good way. Plus they look good with my trusty Isabel Marant belt, but then again, so does everything, right? I was also very proud of myself for wearing heels in the first time in over a year, but these are surprisingly comfy. 

What to wear in October

I was feeling the Meg Ryan fall this year, and this outfit felt very autumnal to me, in the best way possible. It has some of my favorite elements—my J.Crew sweater blazer, Chanel ballet flats—as well as some that were new to me, like the Nili Lotan x Target floral skirt. My only regret about this shoot is that I wish I had taken off my blue bracelet from our hotel in Hawaii (although clearly I wanted to hold on to that vacation feeling!).

What to wear with a cashmere coatigan

This outfit feels very "me" and has some of my favorite things: leopard print, stripes, my Isabel Marant belt, and most importantly, the cashmere coatigan that Sean gave me for Christmas last year. I practically live in the thing during the winter months, and while I also featured it in this outfit, I didn't include it here because the dress got super pilly and off to the scrap pile it went. Also, in spite of being featured twice here, I ended up selling these Levi's because they got super saggy. And so my search for the perfect '90s jeans continues...

What to wear in December

I was happy to end the year with an outfit that felt very true to me, even though the dress was a little outside of my comfort zone in terms of colors and designer (I think this is the first Tory Burch thing I've ever bought). Also, I freaking love the Birkenstocks I'm wearing here and predict they'll be one of my favorite pairs of 2022. Expect to see a lot more of them in the new year.