Cheryl Shops

This week's outfit post is a bit different than my usual format, and it's all the weather's fault. May is usually a gorgeous month in San Francisco, but it's been unseasonably cold—it's even been raining lately, which is unheard of for this time of year. I had planned on wearing the first look featured here, but brought warmer layers so we could go out to dinner afterward. As it turns out, my warmer layers looked cute too, so we just ended up shooting both outfits. One is more dressed up and polished; the other is more casual and cool—and I can't decide which is my favorite, even now. Let me know what you think of this new format in the comments, and if it's a hit, I'll do it again from time to time.




First of all, here's the dress I started with. I have randomly rediscovered H&M after finding the perfect pair of black skinny jeans there, which is where I found this dress. The print is very millennial—pink, palm leaves, leopards—but the cut is super flattering and easy to wear if you are not-so-millennial. The fabric is a lightweight rayon and kind of wrinkles a lot, but for $24.99, I'm not complaining. The fit is true to size—I'm in a 6.


This is how I had originally intended to wear it—with a lightweight leather jacket (last seen way back here) and my Chloé pumps (you last saw them in Russian Hill). Together, this look is definitely more polished; the jacket and shoes are both bigger-ticket items, and the taupe-nude shades are elevated and sophisticated. I also have my new Staud bag (just seen with a pink blazer) in both looks, but I think it works, since it's such a simple, streamlined shape.


I love this jacket but sadly don't wear it enough; it runs a tad on the small side, so I counter-intuitively have to wear it in warmer weather over something pretty lightweight, such as this dress. I'm in a size medium, and while this color is several seasons old, Vince makes this jacket every year, and I've linked a gorgeous olive green version below, currently on sale (!).


For some strange reason, I tend to wear these Chloé pumps in warm weather with bare legs, which has a flattering effect if you have lighter skin like I do. Whenever I wear them, however, I'm reminded of how comfortable (and how cute) they are—and of the fact that a really, really nice pair of pumps is totally worth the investment.


OUTFIT #1 DETAILS: Vince jacket (current version here) | H&M dress | Staud Bissett Bag | Chloe Lauren pumps (more sizes here)


When I want to wear something springy but the weather is not cooperating (sadly a more frequent occurrence lately), I just add knee-high boots. Of all the ones I own, these ancient Zara riding boots looked the best with the color scheme of the dress...but then the leather jacket I was wearing looked all out of place in terms of tones and level of dressiness. So I subbed in my trusty J.Crew field jacket (last seen over a shirtdress) and that felt better to me—kind of a safari vibe, but definitely a more casual interpretation of the outfit.


This is what I actually ended up wearing to dinner; in spite of being a much lighter-weight fabric, this J.Crew jacket is somewhat on par warmth-wise with the leather jacket. Go figure. I really like how it looks with the jungle print, however—it kind of feels like '80s Banana Republic, when they had a safari theme. (Hopefully I'm not the only one out there who remembers that!)


Clearly I've had these riding boots forever, and even though the toes are scratched beyond belief, I can't bring myself to get rid of them. They are long overdue for a good polishing, or maybe even a trip to the cobbler. This pair is from Zara, but I've linked a very similar one below.


OUTFIT #2 DETAILS: J.Crew jacket (current season here) | H&M dress | Staud Bissett Bag | Zara riding boots (similar here)


Which outfit is your favorite? Want to see more posts like this? Tell me in the comments below!