Cheryl Shops

I remember my first pair of denim shorts. I had just seen Dirty Dancing and was obsessed with the pair that Jennifer Grey wore as Baby. Like hers, mine were long and fitted almost to the knee with a rolled cuff. I wore them religiously until they didn't fit anymore, and while I have owned many denim shorts since then, I haven't loved any of them as much as that first pair. While I was very into them at first, I don't find myself reaching for the Madewell shorts I bought a few years back and as the years pass, I'm feeling more wary of shorter shorts. That said, I do enjoy shorts as an option when the weather is warm, and as a denim lover, I'm always up for an alternative to longer jeans. I was influenced to buy a pair of uncharacteristically (for me) baggy denim shorts from Old Navy—I sadly can't remember which Substack newsletter had recommended them—and when I first tried them on, I thought these are not for me. But then on a warm Saturday afternoon when I just wanted to be cool and comfortable, I decided to give them another try. This time I was wearing a slim-fitting tank top and all of a sudden it came together: You can wear baggy denim shorts without looking sloppy. It's just a matter of getting the proportions right. 

I am finally at the age where I don't feel compelled to try every trend, however I do give them a whirl when the mood strikes. Earlier this year, red tights staged a comeback—I tend to think of them as very '80s, but they definitely had a Gossip Girl (the original) season 1 moment in the early 2000s—and while I wasn't quite ready then, a display at my local Target caught my eye (I know, right?!) and all of a sudden, they seemed like the perfect thing to wear right now. Here's how I styled my red tights for a holiday party. 

Back in the early '90s when I was a grunge-loving teenager who shopped equally at Salvation Army and Contempo Casuals, I remember my mom favoring a type of shorts that were long, pleated, and occasionally decorated with a bold floral print. I was perhaps a bit embarrassed when she wore them (sorry, Mom!). Thirty years later, this exact style has flooded my Instagram feed, and to the mortification of my inner 15-year-old, I found myself wanting a pair. The funny thing is, I saw lots of chic young women wearing them, not just 40-somethings, so maybe that's what really made me go for it, or at least justify it. Maybe we really do turn into our mothers after all? Regardless, read on for a mini review of the shorts I ordered and some styling tips. 

A very dear friend of mine always jokes that she never makes it into my IG stories whenever I visit New York, and I always respond that it's because I'm so present and having so much fun with her that I don't even think to pull out my phone and take pictures. The same thing goes for this post—I had every intention of shooting a different outfit every day of our five-day trip last week, but...we were having too much fun and kind of forgot to. The good news is that we did manage to capture two of them (I'll re-create the others sooner or later), and coincidentally enough, they both kind of reflect the areas of the city in which I wore them. Here are some of the things wore last week in NYC.

My love of black pants probably began when I was in college. I had a pair in a stretchy boot-cut polyester from Contempo Casuals, where I worked, and they made me feel very chic and grown-up. I wore them out to parties and bars, with going-out tops of course, or with a more demure sweater or blouse when I needed to look polished. Conservatively speaking, I probably own about 10 pairs of black pants at the moment, and yes, I wear them all. Some of them are skinny—a silhouette that I truly don't think will ever go fully out of style—some are straight leg, but what my closet has been missing is a true menswear-inspired wide-leg trouser. I've been searching for the right pair for awhile and have had some misfires, but I've finally found The One, and it's so good, I've been living in this pair for the last month or so. Styling wide-leg pants can be a little tricky, especially if your closet is heavy on longer tops (which look better proportionally with skinnier pants), but I'm here to help. Here's what I'm wearing with my wide-leg trousers.

Inevitably, toward the end of each season, I start to get completely tired of all my clothes and am seized with an overwhelming urge to go buy a bunch of new things. The older (and wiser) I get, the more I try to be as pragmatic as possible about this. I want to make sure I'm investing wisely, and that I'm not going to buy something, wear it for a season, then never wear it again. So before I buy anything new, I've been asking myself three questions: 1) Would I wear this even if it weren't "on trend"? 2) Is it the best quality I can afford at the moment? 3) If it truly doesn't work for me in the end, can I resell it? These three questions have definitely made me slow down and be more conscious about what I'm buying, and that said, everything in this post obviously passed the test. Here are the 5 spring must-haves I'm most excited about.

If it seems like I'm traveling a lot lately, well, I am. I have always loved to travel, and the pandemic pretty much brought that to a screeching halt, so now that life has (pretty much) gone back to normal, I'm making up for lost time. My day job is also 100% remote, which means I can work from anywhere, so when Sean has a business trip in an interesting location, I tag along. And lucky him, he had a work conference in Honolulu last week! Flights from San Francisco to Honolulu were very reasonable and I had a free place to stay (thanks, Sean's work!), so it was kind of a no-brainer. (Although, to be fair, my workdays started at 6:30 a.m., which was an adjustment to say the least.) I mean, who's going to turn down a trip to Hawaii? (Not me!) Here's what I wore.

Today is my birthday and I'm 45 years young. I say that because strangely enough, I don't feel like I'm in my mid-40s—I still kind of feel like I'm in my late 20s—and in terms of looks, well, let's say I'm making the most of it. When I was turning 30 (which I was freaking out about at the time, hahahaha), a friend asked me what 18-year-old Cheryl would think of 30-year-old Cheryl, which made me put things in perspective. While many things have changed since then, I remain pretty damn happy with my life overall, and I hope that shows, inside and out. Tonight I'll be celebrating with friends, followed by dinner at one of my favorite restaurants in San Francisco, and here's what I plan to wear. 

 Is it me or has all of the marketing around Valentine's Day gotten a little toned down recently? I feel like I used to be inundated with emails and sponsored posts and pitches and ads—and I still see them, of course—but now, if anything, the tone seems to have shifted to an empowered one (buy your own diamonds!) and/or a more low-key one (date night looks to love). I realize I've done a lot of Valentine's Day outfit posts, including a Galentine's Day last year, and since it's been a whopping six years since I've done a date-night post (and oof is that one outdated!) I thought now would be a good time for an update. Also, we rarely go out on Valentine's Day; if anything, we tend to stay in and cook a nice meal at home since restaurants tend to be a sh*tshow on V-day. So since it's still February—and still cold here—this one is on the cozy side. Here's what I'm wearing on date night. 

It's my last outfit post of the year, and while I love everything I'm wearing, to be honest, I don't think that it's all completely working together. Three of the things are new, and I wanted to get them all up on the blog as soon as possible because I'm excited about them and wanted to tell you about them. But I will admit, I think I was trying to make fetch happen a little here. It's okay—bloggers are not perfect (god knows I am not) and sometimes we make outfitting mistakes. That said, there's a lot I do love about this look. Here's how it all came together.

In case you missed my Croatia travel diary last week, we spent 12 days in Croatia in September, starting with two nights in Split, then a week on a chartered boat, and finally three nights in Dubrovnik. (And I actually started the trip with four nights in Vienna, but that's another post for another day!) My challenge was twofold: first, packing clothes that worked for both land and sea, and second, fitting them all into a carry-on, because I had a connecting flight in Frankfurt and had heard horror stories about lost luggage. So, yes, I managed to pack enough clothes for two and a half weeks in a carry-on—it's all about packing cubes, but I also made sure that everything I brought could be worn at least two different ways (you'll see several items get repeated here). This isn't everything I packed (swimsuits and cover-ups, for example), but these were definitely my go-to pieces. Here's what I wore on vacation in Croatia. 

Happy first day of autumn! For many of you, it's the time of year that a cold nip starts creeping in at night, and you start thinking about boots, sweaters, and pumpkin spice everything. Unless you live in San Francisco—then it's finally summer. After months of getting pummeled with wind and fog, we now get consistently sunny days and temperatures in the 70s, and it's glorious. Of course, it's also a little weird, because it's fall and you don't necessarily want to be parading around in bright colors and airy fabrics as you would in actual summer. Thankfully, I've devised an outfit formula that feels seasonally appropriate yet warm-weather friendly. Here's what to wear in San Francisco in fall. 

Hi, remember me? I feel like I've been slacking a lot on this blog, and literally the last thing I want to do is turn into that blogger who tapers off into nothingness. (Um, like when I ended up taking a three-year break awhile back.) The truth is that I have been working my heinie off, partly because we're neck-deep in holiday at the moment, and partly because I'm about to take the longest vacation I've had in probably 7 years. So to give you fair warning, I am going to take the first two weeks of September off and really unplug—like, not-take-my-laptop unplug. But in the meantime, I've got a few posts planned, and in the spirit of vacations, this one is all about the caftan. Caftan? Kaftan? I'm going with a C for Cheryl. Caftan it is! Here's my favorite one and how I'm wearing it. 

Have you ever meticulously packed for a trip, only to arrive and experience a sudden change in weather? That's what happened to me last week. I had been checking the forecast for a week and having lived on the East Coast for years, knew I was in for humid, mid-80s temperatures with lots of sunshine. Except I forgot the biggest rule of East Coast summertime weather, which is that it can change at any minute, and that's exactly what happened, whoops. Thankfully I did bring layers and a few warmer things, so while this outfit didn't turn out quite like how I had planned it—in fact, it shares over half of its elements with what I wore in this recent post—I'm still pretty happy with it. Here's how it all came together.

One of my favorite parts of living in San Francisco is that it's so close to wine country. If you time it right, you can be in Sonoma County in under an hour, or a little longer for Napa County, but not by much. While wine tasting is obviously a big part of the experience, for me, the best parts is getting outside, breathing in some fresh country air, and enjoying the weather, which is usually 10–20 degrees warmer than in the city. If you follow me on Instagram, you know that I go to wine country quite a bit (I call my outings #SundayWineChurch), so I feel like I've perfected dressing for the nuances in weather. Here's what I recommend wearing in wine country in late spring. 

As I mentioned in my newsletter last week, I've been hearing a lot about dopamine dressing, which is basically wearing clothes that bring you joy because the last two years have been all about sad sweatpants and scuzzy slippers, and we're all OVER IT. So as I enter my 44th year on this planet—yes, today is my actual birthday—I am fully embracing that concept. This week's outfit feels very "me" on several levels. For one, it includes some of my favorite pieces. On another, it pays homage to one of my favorite Peter Lindbergh editorials from Vogue, featuring all of the supermodels draped over motorcycles in Dumbo, dressed in a mix of Chanel and Schott. But on the deepest level, this is how my inner child would like to dress, ballerina skirt and all. And I'm totally embracing it. 

Just before the new year, there was a meme going around the Internet alluding to how 2022 sounds like "2020 two," e.g. "the sequel," e.g. dear god, not again. But Sean interpreted it as "2020 take two," e.g. a do-over, and that optimism is one of the many reasons why I love him. Yes, things may be less than ideal right now, with closures and quarantines and yet another rampant strain of Covid, but maybe, just maybe this is the year we move on from this @#$% virus. I didn't realize how much I was craving my old routines until our back-to-office date got pushed back for the gazillionth time—and this time I was actually disappointed about it. I had been thinking about easing back into office wear (and really looking forward to wearing my blazers again), but since that won't be happening just yet, I've come up with a happy medium: pieces that are comfortable and casual enough to wear around the house, but polished enough to wear out to after-work drinks (outside, of course). So here's what I'm wearing in 2022...for now.

Historically speaking, I've featured party outfits in December, and omicron variant be damned, I do plan to do my fair share of partying this month. But I also thought I'd end the year with a more true picture of where my wardrobe is at the moment. I had a bit of an identity crisis earlier this year; after months of wearing little more than sweats, I was like I NEED FUN CLOTHES and ended up buying a bunch of stuff that just wasn't me. Not that I'm not fun, but I can be fun without looking like I'm in a funhouse. Anyway, I like neutrals—always have, probably always will—and while I might not have the most interesting wardrobe in the world, it's the right one for me. So with that in mind, here's to ending 2021 on an authentic note. 

If you've been reading this blog for awhile, you know that I used to live in NYC for a long time (13 years, to be exact) and it will always have a big part of my heart. I normally go back for a visit at least once a year, but thanks to the pandemic, I hadn't been there since January 2020. When I've been gone for too long, I can almost feel it in my bones; spending even a couple of days in New York is like a defibrillator for my soul, in the best possible way. Even though he's never lived there, Sean loves NYC as much as I do, so convincing him to go there for a long weekend in celebration of his birthday required only minimal arm-twisting. Of course, after having been away for so long, I had no idea how New Yorkers were dressing, and if you've been reading my newsletter, you know that I've been panicking about what to pack. I may not have totally blended in—I've been a West Coaster for 8 years now, after all—but I could at least hang in this outfit.