Reader Question: What to Wear – High School Reunion



Ahh, high school.  Such fond memories of, well…..hunh.  To quote Amanda, “back when I was soooo well rested.”  And apparently back when duck face was still OK to do (OMG Cam!).

In high school, I was doing responsible things like running for a class office, which sounded like a good idea…..but no one pointed out the fine print:  winning means that you’ll be planning class reunions for the rest of your life. My 20th high school reunion is this summer and my friend and I (neither of whom actually live in our hometown) have been hard at work planning the event.  So, when I read Heidi’s question on our Facebook page, I could totally relate.

Hi! I need ideas for a dress and shoes for my 30th high school reunion the end of July. Casual chic. I’d like to show off my hard work but not be too sexy. Thanks!

What to wear around people you haven’t seen in forever….and be all “casual chic”?  (Thanks for nothing, dress code.)  This is tricky.   Conceivably, you could get away with jeans, serious shoes and a fancy top, but a much safer (and more fun!!) bet is to stick with some sort of gorgeous dress (or romper), and then dress it down with simple wedges, flat sandals, or unfussy hair.  The note you want to hit is Fabulous, Without Trying Too Hard.

And I love that Heidi wants to show off her hard work.  Here are a few thoughts….nothing overly fancy, just cool and chic.  Uh….”casual chic.”



1. Anthropologie Del Mar Halter Dress – I love the print on this dress. This emerald is a gorgeous color and I love how some of the print detail points in at the waistline = flattering. Wear simple gold hoops and a couple of bangles. You don’t need much since the print is bold. $148

2. Nine West Bellermo Wraparound Tassel Sandal – These are good. I’ve had trouble committing to any block heel shoes, but I love how the ties on these keep them feeling feminine. $108.95

3. JCrew Short Sleeve Cotton Shirtdress – This simple black dress has really great details. The collar keeps it casual and chic and the sleeves hit at a really flattering spot. I love this dress and the slightly sporty vibe. One of my faves. I’d wear a brushed silver cuff and earrings in the same metal. $98

4. Kelsi Dagger Mackie Wedges – I adore these. They are modern and fun, but will keep legs looking long with the nude color at the ankle. Gorgeous with most LBD’s. $160

5. JCrew Flutter-sleeve Eyelet Dress – Yes. Yes to the modern take on eyelet fabric and yes to this pop of color. I love the sleeves, too. Too keep things casual, skip the necklace. I paired it with black textured heels, but it would look great with a nude gladiator or wedge, too. $138 (25% off with code SHOPNOW)

6. Louise et Cie Hyacinth Ankle Strap Heel – Love these. They have a tiny dot print that gives them a bit of interest. Also, the heel is low enough for standing at events. Super flattering on legs you’ve worked for. They also come in a gorgeous bright orchid color that would be lovely with black or white dresses for summer. $128.95




1. Anthropologie Nolita Maxi Dress – Love. Stripes. Yes. This one is so gorgeous and classy. Wear with either a more rustic/hippie tie sandal like #2 or the fun gladiators on #6. I would pair it with fun boho accessories (like a stack of leather bracelets) to keep it from being too preppy. $158

2. Free People Dahlia Tall Gladiator Sandal – So pretty with the metallic leather, but love that they are a bit more rustic. Just lovely. $68

3. LOFT Beach Halter Jumpsuit – So, I know it’s not a dress, but the right jumpsuit can be perfect for summer events. The neckline of this suit is super flattering and I love the slim cut of the legs. Wear with a gold cuff bracelet.  $74.99 (30% off with code FIRSTLOOK or 40% off with a Loft card)

4. Dolce Vita Linsey Lace-up Wedge – I’ve been in love with these for a while. I think they’d be the perfect summer dress shoe. I love the cutouts and a wedge like this is great for any events on grass (no heel sinking in.) $139.95

5. Anthropologie Celane Lace Dress – This dress. Gah. It may be a bit on the dressier side, but I had to include it. A bright gladiator sandal keeps it more casual. Stick with simple jewelry, too, so as not to be too fancy for casual chic. $268

6. Joe’s Teddy Gladiator Sandal – Love these. Wear with black & white, any gray and indigo. So good to have a fun red or orange sandal in your closet. $144.95

Shop These Looks and More Finds


At my 10 year reunion Facebook wasn’t widely popular yet, so this one will be both more and less weird after having connected with a few friends there. I am getting to see a few really close friends, though, too, so I’m definitely excited.

But, even after helping choose all of these options for Heidi, I still have no idea what to wear to my own! Would love to hear your suggestions! Thank god I at least have a better haircut than in this photo below, though. Sheesh. My mom is away from home right now and apparently this was the only high school photo of me she has on her computer. Thanks, mom.

Screen Shot 2016-05-16 at 11.25.40 AM

Heidi, I hope you have a great time at your reunion and I hope I’ve provided at least a little help!




  1. Great job Laura! Nearly every one of my social events calls for some variation on causal chic. Great ideas to bookmark for summer parties in general.

  2. I LOVE THIS! Thanks for the help because I was CLUELESS, and now I have some really great ideas!!! Your 1996 hair was ahead of the curve. Remember everyone going short in college?!

  3. Great choices Laura! I hate events that are “casual chic” or “dressed down formal”…too confusing and then I panic trying to fit myself into the theme instead of just rocking with what makes me feel great. Love the JCrew shirt dress and heels combo! Hope we get to find out what the reader wears!

  4. I have those Dolce Vita wedges, they are gorge! I wore coated denim, a lace top & strappy heels to my last reunion which was held at a bar.

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