What To Wear To A 40th High School Reunion?

Ah, high school reunions. What to wear in the face of remembered adolescence, undeniable aging, and a flutter in the heart?

The Grande Dame doesn’t attend these things. She throws a shindig, people come to her. Or not. She’s learned to pretend she doesn’t care. She does fly East for the significant Smith and Vassar reunions, but so many of her classmates participate in her fund-raising efforts it’s only right.

Nor will you find many Artsy Cousins in the undifferentiated crowd. Ms. Artsy got out of town as soon as she could, and spent the summer in Istanbul. When the event is moved to Ha Noi, she’ll consider showing up.

But the Sturdy Gal, she who follows every rule, some that haven’t even been written, she is there. In the gym, the auditorium, the local Hyatt ballroom. And even our Gal knows she’s got to put aside her favorite corduroys and get Dressed.

Imagine a return for the 40th reunion. We are not yet 60. We are no longer 45. We are still women.

What to wear to a high school reunion?

What rules should our Gal follow here? Let’s deconstruct her possible goals.

  1. Look beautiful
  2. Show no sign of the effort it might have taken to look beautiful
  3. Evince desire
  4. Show no signs of trying to evince said desire
  5. Dress to manage fluctuating temperatures, brought about by over-enthusiastic air-conditioners, or throngs of sweaty dancers
  6. Avoid foot pain at all costs

Her rules, then, as follows.

  1. Wear a dress or skirt with some movement, some ease. Leave the trousers behind and you’re immediately festive enough. It’s tough, Sturdy Gals feel more comfortable in pants, but have courage.
  2. Show the parts of your body that give you joy. Often it’s our biceps. All that gardening and carrying of other people’s boxes. But if it’s your legs, choose a short smock dress and wear heels just a half an inch higher. And if it’s your waist? Go you.
  3. Choose one item with shine, not more. A satin skirt, or a sequin t-shirt. Shine means you’re trying.
  4. Pay attention to your outerwear. This is not the time for wraps, you will be fidgeting with yours all night and those things just will NOT stay put on chairs as they are told to. Sturdy Gals like to match, the rest of you have somewhat more subtlety.
  5. Mid-heel pumps are comfortable, but elegant, if you find the right shape. Amp up the desire meter with patent or snakeskin. Tell yourself they are sensible. Define sensible very broadly.
  6. Lots of mascara is OK. It’ll be dark. People will not want to put their glasses on. By the same token, wear red lipstick. This is not an occasion for disappearing mouths. If you just can’t do bright lipstick, find some red lip balm. Apply often.

The final required accessory? A friend. Bring company. Or make a date to meet someone you know upon arrival. Some of us need to survey parties before diving in, others like to wade through the room. Either approach is infinitely better with a pal in hand.

By the way, if you haven’t taken a look at Anne M. Cramer’s site, and you’re a fan of classic, yet slightly subversive clothing, I recommend a visit. Take a look at the rough waistlines on otherwise polished skirts. (Note: Anne doesn’t do clothes any more. But we will find you something that works just as well.)

What To Wear To Your 40th High School Reunion In 2016

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  • It can’t be your 40th high school reunion yet, unless you graduated at 15? Mine was last summer. A ridiculous time (mid-July) to hold one, as so many, including me, were traveling. But I did have fun planning “virtual” outfits to wear anyway. I love the part where you wrote that no one would be wearing their glasses, so a bit more makeup would be OK!

  • I’m with Kathy – I know you’re not yet 58. Did you graduate early? I wouldn’t be surprised if you did.

    And a hearty “Amen!” to avoiding foot pain at all costs.

  • I love the satin aqua top, very pretty.

    “…she who follows every rule, some that haven’t even been written” made me smile.

  • I haven’t attended a high school reunion yet, and I suspect I’ll make it through life without (never say never, tho’, right?). My Artsy Cousin is clearly overruling my Sturdy Gal, so far, at least.
    But I will definitely bookmark Anne Cramer’s site to investigate later whether she ships this way — wonderful stuff there.

  • I must be an Arty Cousin — I got as far away from high school as I could and never wanted to look back. Ah, all those dynamics of looking like you’re not showing desire when you are, looking like you didn’t make an effort by making a massive effort. Don’t miss it much.

    But I do love the skirts!

  • I love, love, love Anne Cramer! I’ve wanted the Flynn skirt forever. Now I want the Parfait dress too. Tagline: Her idea of cleaning was to sweep the room with a glance….


  • Thank you for sharing the Anne C. Cramer site. Finally some sensible clothing from US!
    Good US advice too ; )

  • Sound advice – but most of the people I went to school with ended up in jail, I won’t be going to any reunions.

  • Great advice – I found myself nodding at all your suggestions (am sure I am a little bit, no, perhaps a lot – sturdy gal!) – especially following all the rules or maybe that’s a Capricornian trait? Love the ‘this is not an occasion for the disappearing mouth’ comment. Oh, and those gorgeous shoes! Brilliant post. x

  • “People come to her. Or not.” Phrase of the day, to be sure. You will laugh to hear that I sighed aloud when seeing your polyvore, it is that lovely. Off to visit Anne M Cramer, although the word subversive has me terrified. (Heh, heh, heh.)

    Sending you a smile Miss LPC.

  • So many of my former classmates (and fellow students from other years) have returned to the area that high school reunions are now a thing of the past and have been replaced by a rolling schedule of multi-generational, informal drinks parties held at the local country club every three or four months. Should I ever consider attending, I would heed your very sound advice (although I am not yet 45). I absolutely love the grey wool and satin and pearls.

    But I am unlikely to attend. Those whom I wish most to see have, like me, wandered far and wide across the country and the world and don’t return home very often, if at all.

  • Wow!!!! Lisa… You went WAAAAAAAAY over the top! For all of you wondering fans, I posed this question to Lisa a couple of times over the past month and the web site was not allowing her answer to be posted in return. So now all of you know what to wear when your time comes!!!!!!!!! I’m the old one! HAHAHA
    Love what you’ve done, LIsa. i’m going to share it with my good friends form home.

  • Those are my unwritten rules for ANY event. But I shall bring them with me in case I ever attend a high school reunion. Also, “3.Evince desire
    4.Show no signs of trying to evince said desire” – YES YES YES

  • Looking at recent photos from my sister’s reunion I think snapping a few trial photos is a wise idea. In this day and age people will be taking lots of pictures and some will end up on Facebook.

    Make sure your your outfit photographs nicely. If you look wrinkled and messy in your dry-run photos you’ll certainly look that way by the end of an evening of “Crimson and Clover.”

    Your modest skirts and high-necked blouses that can highlight good looking bling appear to be excellent choices on that account.

  • As I went to school in Singapore, it’s been rather easy for me to avoid reunions. But this is sage advice if I ever do get the urge …

  • Lisa,
    I like your suggestions and I would have been tempted to wear a wrap and probably would have regretted it for the very reasons that you mention.
    Such good advice on all fronts.

    BTW It was my husband’s 40 this year and he opted out…when we saw the photos online we did not recognize one person!

  • I have been drooling over the Anne M. Cramer site for a week and debating whether I could wear that very skirt in black to a 50th birthday party at a penthouse on Central Park West. What do you think, Lisa? With black tights, black suede pumps, a bronze tank with sequins and a bronze metallic cropped cardigan. I’m a Sturdy Gal with Artsy Cousin influence and never have any grown up dressy clothes appropriate for “cocktail parties followed by restaurant dinner”. Help!

  • I am one who generally stays away from reunions, although I have gone once and enjoyed it; plus felt great about myself.

    Why do the women look so good and many of the men look so OLD!?


    Art by Karena

    6:58 pm
    Pam said...

    @Karena, I thought the other way around. To me, men improve with age, women get older.

  • Hi Lisa, This is a great and timely post! I actually have my 15th reunion coming up. Would you alter the suggestions in any way for the younger set? Thank you.

  • True to my Artsy Cousin self – wild horses couldn’t drag me!


  • Just an addendum to Lisa’s point #1. If you’ve resisted buying that magnifying makeup mirror this long, now’s your time. There’s no sense getting gorgeous if you overlook an errant hair on your upper lip, or beneath your chin. Here’s why: your classmates are all wearing trifocals now, one of the three lens strengths is a veritable zoom lens. [Goddesses are in the details!]

  • I just attended my 39th reunion (long story) of the girls school I attended. About 30 attended, and I have to say it was the most amazing experience. All the cliques, mean girl, sad stuff was gone, and it was a just charming bunch of women just enjoying each other. I say, if it’s your 40th (or 39th), you should go. You will be so pleasantly surprised! Lisa is absolutely dead on on the way to dress-I only wish I had her tips before I attended.
    aka Muffy
    Artsy cousin/sturdy girl

  • Kathy – I added the details on just whose reunion it was:).

    Jan – Although I don’t think I’d wear Crocs to a reunion, even the Corporettes are now extolling their virtues.

    Susan – That shine and color are your style.

    Mater – I think your Artsy Cousin is rampant:).

    Cynthia – It’s so nice to grow up, isn’t it?

  • Patsy – Why not? I can see that Flynn skirt with one of your bracelets, easily.

    Mette – Ha! Sensible:).

    That’s Not My Age – Well, yes, understood.

    Sarah – Thank you. Where, we wonder, do our mouths go as we age?

    TPP – Sure you had visited Anne before? She seems right up your alley.

    Staircase Witch – Your class reunion process sounds much better. Especially the multi-generational part of the parties.

  • Jo-De – It was my pleasure, and I’d be honored if you share the post with friends.

    HijabEng – It’s all about not letting the effort show:).

    RoseAG – That’s a good thought. Hadn’t occurred to me, but you’re right. I know taking photos of my outfits for this blog has given me pause here and there.

    Tiffany – Ha! Don’t you get tempted to go back and explore the changes?

    Hostess – So will you attend yours?

    Loretta – Yes I think it is appropriate. More than appropriate, absolutely wonderful, as long as the tights are not too opaque. Black booties would be super Artsy, if you wanted to nudge over on the scale. And I do love bronze, and copper, for metallics. Keep the jewelry small, and matte.

  • Karena – Mysteries of the universe:).

    Danielle – Aha. Yes, I would alter the suggestions a lot. At 33 I’d have been tempted to wear great jeans, a tank top, and a leather jacket. Or a little black dress.

    Darla – Ha!

    Flo – Oh you went there! I know! Chin hairs are the devil.

    Madeline – That sounds just wonderful, very redemptive. And I thank you for the proof point on my outfit theories.

  • Love, Love, Love Anne Cramer!

    8:46 am
    Greta said...

    Thanks for making me laugh at such a time when you are so unsure as to what to wear. It stated casual I am not a casual person I always were bling and love it so I guess I make my own rules! but I loved yours!

    11:29 am
    Lisa said...

    You are so welcome!