Cheryl Shops

I came across a comment thread recently where a woman around my age (slightly younger) was asking what to wear on a trip to NYC and was promptly cut down by someone who probably moved there six years ago from Ohio, who declared that skinny jeans with ankle boots were "a no-go" and implored the woman to trade up to rigid straight-leg jeans with platform boots. Which made me think, "You can pry my ankle boots off of my cold, dead feet," and no pair more so than my Chloe Susanna boots. A version of this style first debuted way back in 2008 but was wisely brought back in 2011 by Hannah MacGibbon, a Phoebe Philo disciple (remember, Phoebe Philo took over as Chloe's head designer after working under Stella McCartney in the early 2000s!). That's when the style really took off—I remember seeing a pair on Sienna Miller—and Chloe has brought it back every year since, cementing its status as a straight-up footwear icon. I bought my pair of Susanna boots back in 2016 (full disclosure: when they were well under $1,000; I still think they're well worth the investment) and to this day, they're one of my favorite and most worn shoes in my wardrobe. I get compliments from a wide range of people every single time I wear them, but more importantly, they just make whatever your'e wearing look that much cooler. So with that in mind, here are 7 different ways to wear Chloe Susanna boots.

It's summer, and that means it's Birkenstock season. Well, that means it's Birkenstock sandal season, because if you're like me, you own what I call Winter Birkenstocks (aka the shearling-lined variety) as well. Then again, you can always wear Birkenstock sandals with socks year-round, so maybe let me backtrack again and say it's sockless Birkenstock sandal season. Whew, glad we cleared that up! I own Birkenstocks in all shapes, colors, and warmths, but my favorite pair to wear in the summertime is the Arizona EVA sandal in black. I actually think they're more comfortable than the traditional cork footbed—the foamy EVA material is more cushiony and absorbs impact better—and they have the added benefit of being much more affordable than traditional leather or suede. (They're also vegan, if that's important to you.) I own them in black and am strongly contemplating a pair in white, because as I'm about to prove, they're one of the most versatile pairs of shoes in my closet. The fact that they're a single color makes them a little more streamlined and sophisticated-looking than the traditional leather-and-cork combination, and I pair mine with pretty much anything. Here are 7 ways to wear the Birkenstock Arizona EVA sandals.

We've had several false starts over the last few years, but it seems like a lot of us are returning to the office, at least a few days per week. As much as I love how productive (and calmer) I feel at home, I miss gossiping with my coworkers and seeing what they're wearing. And when it comes to what I'll be wearing, I have a feeling it won't be a complete return to my pre-pandemic wardrobe—for one, I don't think I can manage a heel higher than two inches—however there are certain pieces that I can't wait to wear regularly again, especially blazers. As I've said many times before, I love a good blazer. Nothing makes me feel more like I have my act together. I haven't been wearing mine nearly as frequently as I'd like to, with the exception of my trusty J.Crew camel sweater blazer. Because this blazer is knit, it feels softer and more relaxed like a cardigan; but because it has a notched lapel and more of a tailored structure, it feels a little more polished than a sweater. One thing to note: this style used to be called the Sophie; it's now the Eloise, and while he collar has been slightly updated and the fabric is a little more lightweight, it's basically the same piece—and a wise investment. Here are 7 ways to wear it. 

Of all the pieces of clothing worth investing in, outerwear is definitely at the top. They're what you tend to wear the most, yet they can last the longest. If properly cared for, jackets and coats can be worn upwards of 20 years, and of course even longer—I have several vintage coats from the 1960s that have aged like fine wine. I tend to feature my outerwear over and over again here on this blog because it's what I actually wear in real life, but also to point out how versatile the pieces I love are. Case in point: I've worn my J.Crew quilted downtown field jacket with everything from denim to dresses. It's funny to think I hesitated to buy it because I was worried it was too close to my other favorite J.Crew outerwear, the downtown field jacket; instead, I like to think of it as the downtown's cooler-weather counterpart. It's the perfect jacket for fall (or spring), when you need something warmer than a denim or army jacket, but you're not quite ready for wool or a puffer. It's so good, J.Crew keeps bringing it back year after year. Here are seven of my favorite ways to wear it. 

 When I do a Cheryl's Greatest Hits post, I generally go for 7 ways to wear something, but I love my white jeans so much—and feature them so often here—that I've decided to go for 10 solid outfit ideas (I even had to edit some out). The key piece here is obviously a good pair of white jeans, and my all-around favorite is the power slim straight from Old Navy, which I'm wearing in most of these photos. It's a fit that sadly does not come in white at the moment, but as an alternative, I'd highly recommend the best-selling OG Straight—it's basically the same fit minus the hidden shaping pockets. I love that the denim is thick enough to not be see-through but stretchy enough to be comfy, and I think the straight-leg cut is super flattering. Plus, the price is totally reasonable. Here are all the ways I've styled mine. 

One of my favorite coworkers used to say "prints are personal," and they are—I love stripes, plaids, and the occasional tie-dye but have a hard time with florals, paisley, and anything abstract. But when it comes to animal prints, leopard is always a yes in my book. I joke that leopard is a neutral (it's made up of neutral colors, after all), but in my opinion, it's one of the most versatile prints around. Here are my favorite ways to wear it. 

OUTFIT DETAILS: Ganni coat | Everlane cashmere turtleneck dress | Cuddl Duds leggings (c/o) | Mango bag | Jimmy Choo youth boots 

I knew several months ago that, for the first time in my 42 years, I wouldn't be spending Christmas in Chicago with my mom. We had instead made plans to drive down to L.A., rent a house in Venice Beach, and have an outdoor, socially distant Christmas with Sean's family. But earlier this week, after realizing that restaurants are closed for outdoor dining, parks and beaches may be next, hospital ICUs are at capacity, and the governor's orders basically prevent interacting with anyone outside of your immediate household, we decided to postpone our trip to February or March. I had been looking forward to our trip for many reasons—a change of scenery, seeing friends and family, traveling somewheres, anywhere—and I'm surprised I'm not more upset about having to cancel it, but I know that it's the right thing to do, and that this is hopefully a one-time-only concession. This year has definitely had its share of disappointments, but I'm trying to look on the bright side. For one, we don't have to deal with jacked up travel expenses, crowded airports, novice travelers, awkward conversations with relatives who have opposing political viewpoints, and so on. For another, it's an opportunity to create our own new traditions. I'm thinking we'll order extravagant takeout from a local restaurant for Christmas Eve dinner, then open a nice bottle of wine and open presents. And as for what I'll be wearing, it will probably be much more low-key than my usual, but (hopefully) still somewhat festive. Here are some ideas, from dressiest to most casualest. 

 It is finally looking like leather jacket season in San Francisco (not to be confused with the rest of the year except for September and October, which is also leather jacket season), so in honor of my favorite time of year, I thought I'd bring you another Cheryl's Greatest Hits featuring seven ways to wear one of my favorite wardrobe workhorses, the leather moto jacket. As longtime Cheryl Shops readers know, I bought this Banana Republic moto jacket several years ago when I worked at Gap headquarters, and while I can't always advocate for Banana's clothes, this jacket is one of the best items they make, which explains why they keep bringing it back season after season. They have miraculously not raised the price since I bought mine—it's still $499, although you can usually get it on sale (never pay full price for anything at Banana!)—the leather is buttery soft, and the thing fits like a glove. A good leather jacket is totally worth the investment and you'll have it for years, so without further ado, here are seven ways to wear it. 

In case you haven't been reading, listening to, or watching the news lately, pretty much the entire state of California is on fire at the moment. I am (thankfully) safe, but San Francisco is currently cloaked in unhealthy levels of smoke (the sky was literally orange on Wednesday) and unfortunately we can't go outside, which means we can't shoot a new post, and thus I don't have a new one for you this week. What I can offer, however, is a Cheryl's Greatest Hits featuring one of my favorite wardrobe items of all time, my Gap Icon denim jacket. The timing is actually quite good, because it's the perfect transitional piece—or, in my case, the perfect year-round layer. So without further ado, here are seven of my favorite ways to wear it.