Valentine’s Day Style: Cupid’s Arrow, Aimed For Your Well-Dressed Behind

Hey girls! are you ready to look, SOOOOOO GOOD!? (so good)

I thought so. Now, as we’re all aware, Valentine’s Day is right around the corner. Whether or not you have plans, let’s look at some pretty clothes to remind us what love is. I have a lot of feelings about Valentine’s Day and Valentine’s Day clothes in general. But I’m going to try to stick to the latter half of those feelings. First of all, I’m not actually opposed to people wearing sweaters plastered with giant pink hearts. I actually think that’s kind of bad-ass and would want to be that person’s friend. However, I am aware that no one in their right mind actually does that, so don’t worry you guys, I’m going to try to think practically.

To kick things off, then, let’s look at something that’s just oozing the love — this adorable vintage ’60s pink plaid dress:

That’s right, FancyCatVintage took plaid to the next level. She actually has a ton of cute dresses so check it out! This is the kind of outfit you’d wear if you were going on indoor picnic date, or, you know, if you actually lived somewhere warm enough that you could just have a normal picnic date.

I’m really a fan of some classy black and white, so don’t feel like you have to wear, you know, a big pink dress; but DO feel free to accentuate the outfit with a hot red/pink shoe. It’s like, yeah I didn’t forget it was Valentine’s day. Now how’s about you take me out to dinner? The shoes are Valentino shoes and can be found loitering around the winter/fall sale section of the site. ‘Cause, you know, it’s spring already.

Another way to incorporate the essence of cupid into your wardrobe is with a scarf. See? This girl’s totally done with her outfit. She’s like Valentine’s Day? Duh. It exists. Like my scarf? Thought so. This particular scarf came from A Peace Treaty which sells almost exclusively scarves. Beware, the steep prices make this more of a window-shopping site, but feel free to poke around and get some ideas of color combinations, or you know, the infinite ways you can actually wear a scarf.

So if you’re like me and can’t actually handle a heel (at least not in the winter, or when there isn’t Salsa music to be danced to), I recommend the penny loafer to be your suave shoe of choice. Penny loafers are adorable. Sometimes they have actual real pennies in them. Sometimes they have tassels. ALL of the time they’re smart and cool like that kid who got better grades then you but was all like screw the system you can cheat off my test if you want because this is all BS anyway. You know? I never actually knew a kid like that, but please enjoy this poorly constructed montage I created to illustrate my point anyway:

You know what’s hot? French things. French kissing, baguettes, Moulin Rouge, Carla Bruni, and berets! Maybe you’re all like, nah I can’t wear a beret. But you totally can. In fact, I’m betting you’d look pretty adorable in a beret. The trick is to wear it with confidence. There isn’t REALLY a wrong way to wear a beret as long as you wear it to the side a little bit and don’t just plop it on your head. Employ the use of bobby pins for optimum security. I once had a red beret, but then I lost it somewhere. Now I have a brown one and it’s still great.

You should probably also wear your beret with a cable knit sweater. A cute girl in a cable knit sweater makes me squeal like I’m watching the puppy bowl and one of the puppies just scored a touch down and/or was disqualified for illegal napping on the field.

Moreover, red berets and cable knit sweaters COMBINED would force me to ask her out on a date maybe to go ice skating or to a bookstore or something. So okay, I did find this beautiful thing in the boy’s section of Ralph Lauren. But hey, they come in big enough sizes that,  if you’re small enough, you should probably definitely pick this up. It’s on a winter sale too, because as we established before, it’s like totally not winter anymore you guys.

Do you have someone you love very much that you need to buy a present for? Then you probably won’t have enough money left to buy these for me:

But you should probably still consider doing so. Marc by Marc Jacobs Fancy Heart Earrings that you can get here. I’m really in love with the “tortoise” inspired thing going on right now because it’s basically the fanciest, most stylish way to wear “brown”, and I really like brown, so I’m glad we have tortoise on the market to validate what I’m already wearing. Small heart earrings in general are really endearing–either to wear yourself or to give as a present.

Moving on, look! Another shoe! I’m obviously really concerned about the happiness of your feet this Valentine’s Day. This one is really artsy and hot and reminds me of Starry Night. Then again, most swirly things remind me of Van Gogh. But I still love this shoe — it’s a Circa X Brooklyn Projects collaboration, for all of you who were wondering. Sneaker-ish shoes like this one (and others) are good for Valentine’s Day because it’s a bit dressier than your average Van/Chuck. Besides this one being namely black suede, the cool chopped wood/chaotic pattern, employs subdued colors keeping it sleek. You can get this shoe on eBay.

Okay, admit it, you kind of love this ridiculous sweater. It reminds you of vampires and love and happiness all at the same time. As far as dates go, for this sweater I’m thinking “you order take out, I’ll set up the projector and get the fire going.” I wonder which vampire movie she’d pick?

Would she break up with me if I suggested Buffy? I guess we’ll never know. Check it out over at Karmaloop, where they also have sweatshirts (and spandex shorts) with giant hearts on them — because after all this, I know that’s really the only thing you want.

El Fin! Now go out and buy yourselves one of those giant heart shaped boxes of mixed chocolates on me. And if people are like, did you just buy yourself all that chocolate? You can be like, nah, Becky from Autostraddle got it for me.

Happy Valentine’s Day!

I'm Becky. I write about style because I think anybody can look great and I think everybody usually does. I'm into self-expression. I'm into being expressive. When I'm not writing about style for Autostraddle I'm usually trying to make a film. I'm also a dancer, so I will Gahu with you anytime, anywhere.

Becky has written 26 articles for us.


    • one of my best friends and i would talk to each other in teen girl squad voices all the time, before she moved to Thailand.

      I think it’s almost relevant to note that she was a teacher at my school (but never my teacher) and the school guidance counselor made some weird comments suggesting she thought we were gay together. (we weren’t.)

  1. i’m kind of alarmed by how attracted i am to that sweater. like, it’s not even that i would be attracted to someone wearing that sweater, although it is def true; i just want to get up close and personal with its wooly cabled deliciousness.

  2. Oh yay! I love when autostraddle talks style to me.

    Good call on pairing some red heels with a black and white outfit.Hot. This Valentine’s Day I’ll be pairing some pajama pants with a hoodie and callin’ it a night.yesss!

  3. i have to admit i immediately went to FancyCatVintage and bought 4 well-chosen dresses (and almost a suede jacket before i realized it was suede, sad face). before i finished reading this post, lol. can’t wait for spring, yah!

  4. I want that sweater so bad. I love fitting into boys clothes!

    I really can’t toss red or pink in my wardrobe, even for Valentines Day- both colors are TERRIBLE on redheads.

  5. Dude, I have a sweater almost exactly like that!
    I cannot believe I am actually in style for once.

    I want those loafers (again) for looking like a grown-up.
    Used to own those, too:)

    Hooray for lesbian fashion!:)

  6. I must have those penny loafers. MUST HAVE THEM.

    Especially the tassled ones. They’re so ugly, but I always love ugly shit. It’s like, you look like my father’s house slippers, but I want to put you on my feet and show you off to all my disapproving friends.

  7. i ordered those circa x bp shoes in the mail because i haven’t bought myself new shoes in YEARS and let me just say that they are just as awesome in person as in the picture. thanks autostraddle! you’re like my own personal oprah.

  8. Becky can we please be spanis galleons? Because none of these styles would make you look burnt, or dead. Teen Girl Squad FTW! my day = 10x more awesome just from this intro.

Contribute to the conversation...

You must be logged in to post a comment.