Cheryl Shops

Full disclosure: I’m planning on spending actual Valentine’s Day in a cabin in the mountains with my friends (and with my boyfriend). But I think a lot of you are looking for date-night looks, because my most-viewed post from last year was what to wear on Valentine’s Day. So in the interest of service journalism (not that this blog counts as actual journalism!), I thought I’d share another idea for this year. Plus, I’ve been featuring a lot of pants lately, so I thought a dress might shake things up a bit. Here’s what I’d wear if I were going somewhere fancy.



As I mentioned a few weeks ago, I am trying not to buy any new clothes in 2020, and I made it through January, so yay me. I am so far finding myself to be more conscious of what I’m purchasing—e.g. not buying random stuff just to feature here on the blog—and one unexpected benefit is that I’ve been discovering items on resale sites that I had missed out on originally. For example, this Ganni dress was everywhere a few years ago and sold out, likely because nearly every influencer under the sun was wearing it. Enough time has passed that it looks fresh again (the cut and print are very classic, to be fair), so I jumped on this one when I saw it for sale on The Real Real. I am super happy with my purchase, although this dress runs REALLY small in the bust—I sewed in a hook-and-eye closure so it’s not all porny on top—and it’s a little sheer too, so I’m wearing a slip underneath. (My mom would be so proud!) If you’re at all busty, I’d recommend sizing up.




Apologies for blinding you with my pasty white legs—it was actually unseasonably warm when we started shooting this, and I brought along my aviator jacket (last seen in a more casual outfit) just in case. Thank god I did, because in a matter of minutes, the fog began to roll in and all of a sudden I was freezing. But therein lies the styling trick: if you are wearing a pretty yet flimsy dress, pair it with a bulkier coat. In this case, it works because of the similar color palette. This aviator jacket was a Zara sale score (and a check off my holy grail list), but I’ve linked a very similar style below.



I’ve featured these red Sam Edelman boots here before (most recently with wide-leg pants) but never before with a dress—I think they work, though! And I’m not normally one to match my shoes and bag, as I think that’s such an old-school rule, but I thought this was a good opportunity to break out my vintage Coach bag, which you last saw with red and leopard (also a cute idea for Valentine’s Day). Jewelry-wise, I’m still rocking my stack of gold bracelets—I have a feeling this could become a signature for me.



This setting likely looks familiar to you—we shoot here a lot, because it’s both somewhat photogenic and also around the corner from our apartment. This store in particular has been in some sort of transition for the last few months, so we were delighted to see they’ve added a window display! We still don’t know what it is, exactly (possibly part of The Future Perfect next door), but hopefully they don’t mind being in the background of so many photo shoots!



OUTFIT DETAILS: Ganni dress (current season here; also like this one) | Zara jacket (similar here) | Sam Edelman boots (similar here) | vintage Coach purse (current version here)