Cheryl Shops

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).




You may remember this black midi dress from this post back in December. Even though, real talk, I weighed about six or seven pounds less when I last featured it here, this dress is very forgiving, thanks to some strategically placed ruching (and, okay, I confess I'm wearing Spanx underneath). Because it's jersey, it's a prime candidate for getting dressed down, since the fabric is more on the casual side. Spanx aside, this dress is very comfortable—it's basically like a very close-cut T-shirt, with a bonus elongating effect.



I'd like to pause here to mention that my butt is getting noticeably flatter over the years. Why is this happening, and how can I reverse it? Any tips would be greatly appreciated.


My trick for making anything appear more casual and laid-back is to add a classic denim jacket. As I mentioned the last time I featured it, this one is nearly 20 years old and just keeps getting better. An important thing to look for in a denim jacket is where it hits—sometimes the cut is too cropped, and thanks to the retro '80s moment that's been happening, sometimes they're too long and oversized. I like mine to hit just at the top of my hipbone. The proportions look better that way—i.e. not equal—with the longer length of my dress.



Moving on to my bag, this is my trusty Mansur Gavriel bucket bag, last seen way back here. I kind of OD'd on this bag a few summers ago, but now that it's not as trendy as it used to be, it may be time for a resurrection. This bag is inherently casual, thanks to its slouchy-yet-structured shape, and it's so big, no one will mistake it for an evening bag. Plus, it's roomy enough to hold a bottle of wine, for an improptu weekend picnic.



The real stars of this outfit, however, are my Golden Goose sneakers. I'd been lusting after them for awhile and finally pulled the trigger during Farfetch's sale a few weeks ago. Some background on Golden Goose in case you're not familiar with them: They're Italian and they're not cheap, but they have a hidden wedge to give you a little lift, and they break in beautifully, with this kind of vintage look. As my feet slowly morph into middle age, I'm finding myself favoring much lower heels; this is my attempt to cling to some level of coolness. That said, I love them, and I hope to have them for years.




These photos were shot around my neighborhood in San Francisco; as much as I love our more exotic backdrops when we travel, I love how these just feel like home. I'm truly in my element, clothing- and location-wise.


OUTFIT DETAILS: Gap jacket || Iro dress (current version here or here) || Mansur Gavriel bucket bag || Golden Goose Superstar sneakers || Stella & Dot luna pendant