Crowdsourcing: What Should I Wear For My Awkward High School Reunion? (Also, My Face Is Cats)

reunion outfit 3 cat thumb

I was not planning on going to my high school reunion. I talk to, oh, six people from my small prep school and three of those are because they wound up going to the same small university as I did. I didn’t really keep in touch with too many people beyond Instagram and Facebook “likes,” so I have no idea what most of these folks look like nor what they’ve been doing, but I am sure it will be a fun time with lots of clams. Oh, yes, it is a clambake.

What I do know is that, given my weird recent bout of obsessive insecurity, I am ever-so-slightly tweaking out over what to wear. I don’t want to dress up too much, but I also want to wear an outfit that says, “Yes, I did grow up to be an adult, teacher-who-told-me-I-was-hopeless.” Granted, I’m not still feeling embittered over that kinda thing, as I generally loved my high school — we had a school cat, dudes — but it would be nice to look…nice. Put together. But still like the adjectives “fun” and “stylish” could apply to me, although I rarely feel like the latter.

Anyway, because I do so many posts the include closeup shots of my face, I figured I’d remove it for these pictures because you’re probably sick of it. Then I realize that that would be very painful and gross, so instead, I poorly edited cats into the pictures. This way, you’ll be able to see my awkward (so, so very awkward) posing and hopefully vote on this poll at the end:

What should Sam, Madame Purrer of Cattister, wear to her reunion?

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Thanks, Glossers!

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    • Jenni

      IS THAT A TATTOO OF A LADY ON YOUR LEG? You should definitely put lipstick on her. If that is what it is. I don’t know. I’m just guessing.

    • WineRanger

      Outfit #2, provided that you are not walking on sand, ugh.

    • Fabel

      Okay, I voted a full cat costume, because I couldn’t just NOT do that. But I’m partial to the tomato shirt/skirt/red heels one OR actually, the dress? And stop it, we are never sick of your face! (although the cats were amusing, for sure)

    • CMJ

      Outfit #2!

    • Steph

      I think you should try outfits 3 and 4 with the fabulous marc jacobs shoes for an additional pop of fabulous

    • Cee

      You have really nice outfits, Sam. I love the prints on your shirts, especially the tomato one. I was stuck between 2 and 4, 2 is sexier!

    • anna

      OUTFIT 2!!!
      I like them all but if you’re going for being a grown up don’t wear shorts. I dress like a giant baby so I’m one to talk but 2 makes you look like A. You know how to wear clothes like a lady yet B. didn’t try to hard to think about it. You just threw something on and it happened to be chic yet playful. You defintley did not ask the internet, that is just how you look.

      • anna

        The top from 4 and shoes from 1 would also work. Basically wear the skirt. Just wear the skirt and you will be good.

    • pinksighs

      Outfit 2! is elegant and sassy, i love it!

    • Alexis H

      OUTFIT 2. That is one of the greatest outfits ever. You also have a really nice collection of printed pieces! Prints are my weakness, too.

    • http://poorgoop.com/ Samantha

      I love the shorts/blazer combination in #3 so much! But outfit #2 is also really great.

    • http://blisstree.com/ Carrie Murphy

      Definitely 2! No to shorts at an event that will likely be awkward enough!

    • Paulina

      You should try to mix the vintage blue jacket with the red shorts from outfit 1 and wear your hair up :)

    • Hanna Brooks Olsen

      I’m really feeling #3. It’s really laid-back and looks like “Oh, is this a reunion? I was just busy living my awesome life and I saw a crowd and came over in between important other things.”

    • mema

      # 2 is adorable.

    • Natalie

      I voted for a combination. I think the shirt from #3 with the shorts, shoes and clutch from #4 would work for you. Throw in a bit of colour either with chunky jewellry and/or lipstick and spend the night looking chic and awkwardly nodding at people whose names you can’t remember. Bon chance!

    • Candace

      Outfit 2!!

    • Darya

      They’re all cute but Outfit 2 screams “I’m a successful grown up, you?”… and from what I’ve heard, that’s what HS reunions are all about :)

    • Amanda Chatel

      I’m torn between 2 and 3. But considering how much you LOVE tomatoes, I’m leaning toward 2.

    • Rebecca

      just an idea….blue shorts, red cherry top, vintage blazer and red sandals. Good luck!

    • A guy

      #5. I’m a guy and a pretty dress will almost always win.

    • seresy

      Blouse and shoes from 2 with the rest of 4 would be adorable.

      (my first comment! Yay!)

    • Anonachocolatemousse

      Love outfit #2! Those shoes are to die for and side note, you could totally pull off a tie.

    • Janet

      the tomato shirt! wear the tomato shirt! It’s cute and quirky and I WANT it.

    • Breezy

      I like all of them a lot, but the short and blazer is my absolute fave. Grown up and flattering and fun. Dig it.

    • Allie

      I vote shirt from outfit #1 with skirt from outfit #2!

    • Chloe Walker

      If you don’t go in there and tell everyone you invented Post Its, I’ll cry.

    • LAbarbie

      Sam, you look very cute in all outfits, especially #2. You should also consider a skater skirt that flares out, I think a short navy one to go with the rest of the #2 outfit would be very flattering for your sexy figure.

    • Kay

      Outfit 3 with the skirt and shoes from outfit 2.