My 10 favorite outfits of all time

I've been feeling a little introspective lately, for good reason: This month marks 20 years (!!!) of Cheryl Shops. I'm planning to go into more detail about this next week, but in the meantime, before I start to look forward, I thought I'd take another look back, this time at my favorite outfits of all time. An important thing to note: I started Cheryl Shops back in 2003 as a way of sharing things that I bought or wanted to buy, as well as sample sales and general thoughts on fashion; back then, this blog didn't have photos, and even so, I didn't start sharing photos of myself until 2017, when I decided to restart it after a three-year break. So while this blog has been around for 20 years, I've only been doing outfit photos for 7 of those years. Now that that's out of the way, I truly enjoyed my walk down memory lane, and I hope you do too. In no particular order, here are my top 10 outfits of all time. 

What to wear with a linen blazer

I decided to start with this look because even though it's 4 years old (and maybe you can tell by how low-rise my jeans look, although I can assure you they're solidly mid rise) this feels most like the direction my style has been moving in lately: classic pieces in lighter neutrals. I still wear all of these items regularly— except maybe the leopard heels, R.I.P. my arches—and this whole look is just a reminder that sometimes simple is the way to go. 

5 ways to wear white jeans in winter

Speaking of lighter neutrals, here's a more recent version from earlier this year; I got so many unexpected compliments on this look, although that's not why I'm featuring it. I've never been a big tuck-your-boots-into-your-jeans kind of person, but for some reason, I like this on me because the white jeans make it feel less expected. Also, I know a lot of fashion people have been tucking their loose jeans into midcalf boots lately, but I think that looks ridiculous; this is just cleaner to me, and it's a good reason to hang onto your skinny jeans, as they tuck without bunching more easily. Also, I could go on and on about how much I love this cashmere blazer; I recently pulled it out of my closet for the first time this season and it made my heart flutter. Hello, lover. 

What to wear with a housedress

This is definitely not the most groundbreaking idea I've ever featured, but I'm including it because it's very representative of how I actually dress on a daily basis. I work from home, but because loungewear is a slippery slope for me personally, I always make sure I dress up a little. And to be honest, this dress is ridiculously comfortable, yet I don't feel overwhelmed by the volume. It was a high-pandemic purchase from H&M; I think I got it for $9 and didn't even try it on because the fitting rooms were closed. (Here's another dress I got that day, that I still wear on heavy repeat.) Here, I'm wearing it with my trusty Banana Republic leather jacket and Vans Sk8-Hi sneakers, which have become my footwear category of choice since the pandemic (again, R.I.P. my arches). The only thing about this outfit I'd change is the clear iPhone holder, which is pretty much an invitation to get mugged nowadays. 

What to wear with a designer hoodie

While I try not to lean too much into loungewear, I am human and did pick up a few pieces during the pandemic, but I justified this oversized hoodie because it's by my favorite designer, Isabel Marant. This outfit in particular feels pretty current because of the red shoes, which were a big trend on the fall 2023 runways. Thankfully this pair is super comfortable, so I will be wearing them lots this year. I love how the Everlane herringbone blazer manages to give this look a little bit of polish, in contrast with the relaxed feel of the sweatshirt and jeans (which I need to wear more often—they're flattering!). For some reason, I tend to shy away from red because I find it to be a little intense, but this is a good example of how a little can go a long way. 

An honest review of Sarah Flint boots

I am still a Sarah Flint ambassador and they've since changed their program, but let me tell you, I sold a lot of shoes for them in order to get them to send these to me. Totally worth it though—these are hands down my favorite pair of Sarah Flint shoes. They are so comfortable but they look so upscale. I was so excited to get them, I had to build a really good outfit around them, so I broke out one of my all-time favorite Dries van Noten skirts (a thrifting find, if you can believe it), plus one of my favorite IRO sweaters and a Zara tweed jacket I picked up earlier this year. Especially with my woven bag, there's a lot of texture going on here, but somehow it all works. 

What to wear in February 

Yep, it's my white jeans again, which I probably should have featured in last week's post about my most-worn items of all time. A good pair of white jeans is hard to find, and what I especially love about these is that they're from Old Navy; what I don't is that unfortunately they don't make this fit anymore (it's the Power Slim Straight, if you get lucky thrifting). They work with so many things (including the boots and taupe blazer above) but I especially love how fresh they look with the camel coat and the ombré of my sweater, which just kind of blends perfectly together. I still wear all of these pieces on the regular and especially want to give a shout-out to Sean for shooting me in such perfect golden hour lighting here. 

What to wear with a pleated miniskirt

This one is from the way-back machine—2018 to be exact, when I wore my Gucci belt with literally everything and Sean and I really started to hit our stride with photography. We shot this in Potrero Hill, the neighborhood Sean lived in when we first started dating, and while I don't want to get too into the behind-the-scenes of this shoot, I remember I was really feeling this outfit. Sadly, the skirt is no longer with us (the elastic waistband stretched out) and I am kicking myself for selling these shoes on The Real Real during the pandemic, because they were so comfortable and made my legs look 8 miles long. I still have everything else though, and I would totally re-create this look, especially if I ever decided to go into my office, which is where I believe I was coming from when we shot this. 

My go-to spring neutrals

With its long-over-cropped-and-wide silhouette, this outfit totally could have gone in a Chicos direction (especially with the comfort sandals, oof) but I think it still looks pretty contemporary, even 4 years later. As I noted last week, this leopard coat is one of my most-worn items in my wardrobe, and I literally just wore the COS pants today (they're my favorite pair in summer). The H&M sweater is long gone, but the Staud bag and MVMT watch are still around (in fact, we shot these photos for a MVMT campaign). If I had to do it over, I probably would have chosen a different pair of shoes for this look, but other than that, I'm still super happy with it.

What to wear with a tie-dye sweater 

For reasons unbeknownst to me, this post is always in my top 10 most viewed at any given point in time; even more inexplicably, it tends to attract a lot of spam comments, which I try to clean up (but if you need help with term papers or recovering lost cryptocurrency, you know where to go). That's not why I'm featuring it, though. Shot during the pandemic (remember when we were all buying tie-dye stuff to cheer ourselves up?) this outfit represents a turning point in my wardrobe, as I started leaning into more relaxed (yet hopefully still cool) pieces. While some of these items have unfortunately been put to pasture (I miss you, threadbare A.P.C. trench!) I still wear the sweater and jeans all the time.

What to wear with a peasant dress

Last but not least, another look from the way-back machine, one that's notable because I still wear everything but the bag (which I think I sold?) somewhat regularly. This dress is the only Loveshackfancy thing I own, but it makes me so happy; breaking it out always signals summer to me. The denim jacket is a classic that you see here on the regular, and in spite of the sandals being completely synthetic, they've held up surprisingly well. I don't know why my hair looks so orange in some of these older photos—clearly I hadn't yet mastered the art of white-balancing in Lightroom, but it's always a good reminder of how far I've come. 


Doused in Pink | Chicago Style Blog said...

Congrats on 20 years! It's so fun to look back! I can see why these are your favorites! All of these outfits are gorgeous!

Jill - Doused in Pink

Nancy 's Fashion Style said...

Oh I love to look back on older outfits! Often I am thinking, why don't I have that one anymore! Your looks never fail!

mireille said...

What a great selection of looks! I love my white jeans too. That mini pleated skirt is so cute and I love that embroidered dress. But my favorite might me the outfit with the brand hoodie!

Laura B said...

20 years! That is truly amazing! It was fun to see your top 10 outfits!


I must say I love all the outfits. I like the style and modesty of them all.

This color suits you. I like cute flare dresses with sneakers. Well styled.

I have a new article, I will like to hear your insight:

ratnamurti said...

Wow. I so love these outfits. You have a real knack for fashion :)

Gail Is This Mutton? said...

Congrats on your anniversary. I love your chic, luux, pared-back style, infused with your own twists. Thanks for linking

Mica said...

This is a great way to look back over your very stylish outfits! It's great you have been blogging for so long too, congrats on such an awesome blogaversary! :)

Thanks for joining the link up!