Cheryl Shops

Let me guess: you're thinking, "You don't look dressed for summer," which could be true if I lived anywhere else in the country but San Francisco, where summer means fog, wind, and temperatures that hit the mid-60s if we're lucky. Earlier in the day when we shot this, it was glorious and sunny (we ate brunch outside and I actually got a little sweaty), but sure enough, late afternoon rolled around and so did the clouds. So long story short, always bring a sweater, which thankfully I did. That said, even if you don't live in San Francisco and, say, have to deal with blasting air-conditioning all season, this outfit will also work. While it's definitely a little dressier than what I've been wearing lately, it's also incredibly comfy (and can be even more laid-back with a change of shoes). Here's how to put it all together.

Kate Moss has been my style icon for as long as I can remember. She's only four years older than me, which makes her the perfect age to idolize—she's old enough for me to look up to, but close enough in age that we're of the same generation. While some may criticize her for not evolving her style over the years, I love that she remains true to herself and doesn't feel the need to "dress for her age." At 45, Kate looks just as cool and sexy as ever. She also has some go-to outfit formulas, and a Who What Wear story dissecting one of them, Kate Moss has been wearing the same outfit for 15 years, inspired this post. The two key pieces are a leopard-print faux fur coat and a little black dress, but I made a few adjustments for winter (and the fact that I don't roll around in a chauffeur-driven car like she probably does). Here's how I recreated one of Kate Moss's most iconic looks.

You probably know how to dress up a little black dress: slip into some heels, grab a clutch, throw on a sparkly necklace, and call it a day (or night, as it were). Dressing one down is a bit more of a challenge—after all, there's something inherently dressy about an LBD. I love to wear one on the weekend though, because I feel somewhat pulled together but also comfy. It's all about the push-pull between fancy and casual, and it's a little unexpected too. But in all honesty, I just wanted to build an outfit around my new shoes (more on those later).

It's the most wonderful time of the year...if you love dressing up, that is. And I do. I have a bunch of party dresses that sit sadly in the back of my closet for most of the year, so this is the time to break them out. Thankfully, I've had a lot of events this season, and lots of excuses to get dressed up!

If you're like me, you probably own a bunch of little black dresses. Mine are all slightly different—and thus totally necessary, right?—but this one struck my fancy because of the length and shape, both of which are unexpected. It's almost a maxi, but it's also rather snug, and while Spanx are pretty much a necessity with this dress, it's somehow also incredibly comfortable and flattering. I bought it at IRO in Paris (one of my favorite places to shop there), and they make more or less the same dress every season—for a good reason.

This leather jacket is by Vince, and it's also a style they make year after year, in slightly different colors. I am a firm believer that leather jackets are something worth investing in (please don't have a heart attack when you look at the price); this one is buttery-soft and just keeps getting better with age. And it can either go dressy or casual.


Since my jacket and dress were more minimalist, I decided to go a little glitzy with my accessories. As I've mentioned before, I work for a jewelry company during the week, so weekends are my time to break out Other People's Jewelry (although I am wearing one of my favorite necklaces from my company). This is one of my favorite bracelet pairings (last seen here) and the ring is an old $5 cheapie from Forever 21 that, in spite of the fact that the enamel has worn off in the back and the metal is decomposing, people ask about all the time. I love how it looks like a vintage piece.



I was planning on wearing a clutch with this outfit and made a last-minute change to my beloved Jerome Dreyfuss bag (last seen here). I joke that this is the poor woman's Chanel bag, but it's also way edgier, so I think it works with the whole vibe here.



Of course, no party look is complete without festive shoes, and my Valentino Rockstuds are pretty much the craziest ones I own. (In a good way.) I last showed these with jeans here, but they can clearly go with a dressier look too. I should also note they're incredibly comfortable—I traipsed all over Lafayette Park (where we shot these photos), then out to dinner and drinks, and my feet had no pain at all. Of course, that might also have had something to do with all the wine I drank. 'Tis the season!



A few weeks ago when I was editing photos and looked a little washed out, and I heard my mom's voice in my head saying, "Cheryl, put a little lipstick on." So I broke out my Sephora Rouge Cream lipstick in Passion Red 03 for this shoot. I'm telling you the exact shade because not only does this color look good on everyone, it lasts all freaking day. Like, you will have to physically remove it at night and you will be amazed by how much color is left on your lips. And speaking of my mom, I look oddly like her in a lot of these photos. Perhaps proof that we really do turn into our mothers one day?



OUTFIT DETAILS: Vince leather jacket (budget-friendly option here) || IRO dress (also here) || Jerome Dreyfuss Bobi Bag || Valentino Rockstud pumps || Stella & Dot Kari necklace || Hermes clic H bracelet, Rachel Zoe tassel bracelet (similar here) || Forever 21 ring

Fashion is definitely having a sexy moment. This may be because we're moving away from the colder, powerful '80s working-woman look into a more optimistic, early-'90s-inspired one. Bandage dresses were all the rage last fall, and they've evolved into cutout dresses, which were all over the spring runways. While cutout dresses come in all shapes and sizes, I think they're actually sexiest when they leave a little to the imagination. Then again, if you are fit and you know it, to paraphrase The Streets, there's no shortage of snug-fitting styles for you. And while I hadn't intended this to be an all-black story, it turns out cutouts are a current (and, yes, sexy) way to update the LBD for spring and summer.

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This Preen dress at first appears intimidating, since the cutouts are at the side, right at the waist and hip. But it has lace insets, which will help hold you in and camouflage any less-than-perfect skin. I also love the asymmetrical detail at the neckline.


This jersey cutout dress by Brit designer Aminaka Wilmont is minimalist sexy, and I love how the wraparound effect of the cutout complements the dramatic back slit.


If you want to try the trend but don't want to expose anything in the hip or waist area, this Michael Kors sheath is a great alternative--it conveys the idea but in a way that's flattering for a wider age and body-type range.


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Max Azria sent a bunch of great cutout dresses down his runway last September; this crepe dress is one of them. The asymmetrical shoulder detail and asymmetrical hem make it a little more interesting than the typical minimal dress.


Another great straight-from-the-runway look is this Alexander Wang ponte dress, which has that athletic look of Wang's spring collection, but is much less gimmicky. Skintight silhouette aside, since most of the cutout detail is in the upper back, it's a slightly more wearable style.


One of the most universally appealing dresses I'm featuring here is Theory's Jacobi dress. Its lower-back cutout is tame in the grand scheme of things, and yet that's an area that, like the shoulders, is flattering for most women. (Note: If you have a lower-back tattoo, I'd caution against this one.)


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This lace cutout dress from BCBGeneration reminds me of the Preen dress above, although its cutouts are even more subtle, and I like how the lace repeats at the hem. This is definitely a nighttime dress, but it has a more classic look that will outlast the cutout trend.


Not at all subtle is this Arden B one-shoulder dress. In fact, if I had to give this dress a name, it would be the "dress to get laid dress." Not that there's anything wrong with that--I say if you've got it, flaunt it.


This Silence & Noise dress, on the other hand, could be called "business in front, party in the back." Not recommended for those who require a bra, it is, nonetheless, quite hot and, on sale for $39.99, quite affordable.