Regardless of how I spend the day, I always like to put a little thought into dressing for it. Here are a few looks that will work whether your valentine is your super serious SO, your best friend (don't forget Galentine's Day!), or your cat:
I also kind of dig the idea of a Valentine's Day date that's kind of rugged and outdoorsy -- horseback riding or hiking or hanging at the local zoo (you know the monkeys are good for putting on an R-rated show). When you might get a little dirty but still want to look glam, I love this red and white striped top finished in the back with sweet bows (going in and out of stock, so keep checking) with comfy ponte pants and practical boots. Red lips and a smart watch add a little sparkle.
Of course, you may need something a bit fancier. I just bought this flirty lace skirt and love the idea of pairing it with a relaxed button down shirt for a comfortable and elegant look. These gold necklaces are so sweet, and I'm kind of obsessed with heels with a crazy floral print. This sheer lip glaze adds a pretty pop of color. Grab your favorite black clutch and you're good to go.
And like the entire internet, I'm obsessed with Self-Portrait's frilly, feminine pieces so if I really had some place special to go I'd splurge on this amazing black and white minidress. My rule of thumb is when your dress is short and busy, you keep everything else simple: flats (these heart-embellished baby pink pair is kind of on the nose, but I love them), a sparkly clutch, and pink lip gloss.