What to Wear to a High School Reunion (5 Weekend Looks)

I’m on my way home from my 50th high school reunion in Omaha, and what a weekend it turned out to be. Coming back stirs something in me. Omaha is my hometown — and it’s where I met my husband, Mak, at the Marriott, of all places, and where my whole world changed. What followed was a life I never could have drawn up: traipsing around the globe with him and three boys, two dogs, and a cat in tow. My family’s no longer in Omaha; both my parents are gone, and I haven’t been back in over thirty years. A lot has changed. Some things haven’t. But a trip home is never just a trip home.

I flew in late Thursday night and checked into the Omaha Marriott — yes, that Marriott. Friday was a happy mish-mash: a run to Regency Mall to pop into Borsheims, my favorite jewelry store; a delicious trout lunch at Bonefish Grill; then cocktails at the Empire Room, where I caught up with old friends and made a few new ones. Saturday was the real treat — a tour of Westside High, then lunch at Big Fred’s, my childhood pizza joint, whose salads I still dream about, with my elementary-school classmates. We reminisced about our teachers and about how we really did walk a mile to school and back in rain, snow, sleet, and everything in between. Saturday also held the visit closest to my heart: time with my dearest high school friend, who couldn’t make it to the reunion. I’m keeping most of that for its own post — but I’ll say this much: there were a lot of tears, and even more love. Saturday evening was the main event, and I dropped in for cocktails, a few more hellos, then Sunday morning was here before I knew it, and it was time to head home again, home again, jiggety jig.

Getting dressed for all of it wasn’t about impressing anyone or turning back into the girl in the yearbook. It was about being comfortable, put-together, and glad to be there. So I packed for the whole weekend — one red thread running straight through — and here’s exactly what I wore and the thinking behind each look.

1. The Travel Look — arrive pulled-together

A flight, no matter how long or short, is no reason to show up rumpled — but it’s also no place for anything that pinches. My formula: a relaxed cream jean (a waistband that forgives a few hours in a seat), a crisp white top, and a cardigan that does double duty — pulled together with warmth when the cabin runs cold. The leopard flat is my not-so-secret weapon: it reads as a neutral, but it adds just enough to keep the whole thing from going plain. The only thing missing? A belt! I added this silk scarf from Ann Taylor for my trip back home.

Shop the Travel Look

The lesson to steal: travel in your layers. One good topper turns comfortable into considered.

Bass Cardigan · White Short Sleeve Tee · Mother Jeans  · Leopard Flats  · Silk Scarf · Horseshoe Bangle  · Caviar Rope Station Bracelet  · Caviar Diamond Link Bracelet · Caviar Watchband · Caviar Two Tone Hoop Earrings · Initial Necklace

2. Friday — the red linen shirtdress for shopping

Friday was my errands-and-treats day — a stop at Borsheims, my favorite jewelry store, and a delicious trout lunch at Bonefish Grill — and I wanted one-and-done ease. This is where the linen shirtdress earns its keep. It breathes, it packs down to nothing, it shakes out the wrinkles, and it looks put together even when you throw it on in five minutes. This one’s Apiece Apart, in a red that set the tone for my whole weekend — because here’s a little styling trick I lean on: pick one color and thread it through the days. Red on Friday, red at cocktails, a red lip on Saturday. Suddenly, a suitcase of separate outfits reads like one cohesive story. May I just add that I received a gazillion compliments. And I am not exaggerating! I ended up wearing leopard flats that I traveled in to save space in my luggage, swapped the earrings, added a necklace and a stack of bracelets, and opted for the T-Lock handbag.

The lesson to steal: a shirtdress is the hardest-working piece you can pack. Add sandals for day, a heel for day, and a lip for night.

Shop the Look

Apiece Apart Red Linen Shirtdress · Similar Shirtdress · Leopard Flats · Bamboo Hoop Earrings · T Lock Handbag  · T Lock Handbag Dupe  · Embroidered Basket Bag · Initial Necklace · Caviar Diamond Link Bracelet · Caviar Rope Station Bracelet · Horseshoe Bangle 

3. Friday Night — cocktails at the Empire Room in a red pleated midi

The first big one — cocktails at the Empire Room. A loud, glittering room, and I wanted to feel like myself walking in. After all, I haven’t seen these people in fifty years.  A pleated midi is my answer for a night like this: the pleats move when you do, they skim rather than cling, and a clean sleeveless crewneck never dates. Since it’s a knit, I wanted a smooth layer underneath — and this was my first time trying Skims. I’m a convert. I went with a bodysuit that’s comfortable — and I do mean comfortable. I kept every accessory gold — sandals, a little metallic bag, a collar necklace, architectural earrings — because gold is the neutral that lifts red without a single thing competing. And the sandals are kitten heels chosen for a purpose. When you plan to work a room for hours, your feet make the call.

The finishing touch was a true red lip from Laura Mercier. With a warm-neutral eye, it pulls the whole look together and lets you skip the fuss.

The lesson to steal: when your dress is the statement, let your accessories all speak one language. Here, that language was gold.

Shop the Look

Red Pleated Midi · Gold Strappy Sandals · Similar Gold Bag · Gold Collar Necklace · Gold Earrings · Caviar Lipstick (Rue di Rivoli) · Caviar Perfecting Lip Liner · Amazonian Clay Eyeshadow Palette · Caviar Tightline Eyeliner · Notorious Mascara Precisely My Brow (Cool Grey)

4. Saturday Daytime — stripes and espadrilles for the school tour and lunch

Saturday started with a tour of the old high school, then lunch at Big Fred’s — my childhood pizza joint, the one whose salads I still dream about — with the friends I’ve known since we were five. Some have remained in Omaha their entire lives, and others like me have moved away. We reminisced about our teachers and how we genuinely walked a mile to school and back. That midday reunion of elementary-school classmates was the sweetest part of the whole weekend. It calls for relaxed but put-together: a blue-and-white striped set with the stripes running different directions for interest, a poplin boatneck top and a drop-waist skirt that’s easy on the body, and a cable knit cardigan over the shoulders — equal parts polish and insurance against a chilly, over-cooled room. On my feet, tan espadrille wedges instead of a flat slide, because the little bit of height and the natural jute lift the whole thing. And the red patent bag (similar here)? That’s my thread again, tying Saturday back to the rest of the weekend.

The lesson to steal: espadrilles are the daytime upgrade that keeps a casual look from going sloppy — comfortable enough to walk in, pretty enough for the matching set.

Shop the Look

Poplin Boatneck Top · Drop Waist Skirt · Cable Knit Cardigan · Espadrille Wedges · Similar Red Handbag · Bamboo Hoop Earrings · Bamboo Bangle · Urban Decay Eyeshadow · Caviar Tightline Eyeliner · Notorious Mascara · Caviar Lipstick (Rosewood Silk)

5. Saturday Night — the little black dress for the finale

Saturday evening was the main event. I dropped in for cocktails, and then it was home again, home again, jiggety jig. For it, I came back to the piece that never lets you down: the little black dress. After a weekend of color and pattern, black is crisp, graphic, and endlessly flattering — and it lets everything else do the talking. I kept the styling sharp: hair swept up and back off the face, one more red lip, a neutral eye. Against black, silver hair reads like a sculptural frame. That’s the whole look — one statement, nothing fighting for attention.

The lesson to steal: the LBD is your safety net and your showstopper. When in doubt on the big night, reach for it and let a bold lip finish the job.

Shop the Look

Black Midi Dress · Similar Black Dress · Similar Coin Necklace · Teardrop Earrings · Bamboo Bangle · Similar Clutch Handbag · Caviar Lipstick (Rue di Rivoli) · Caviar Perfecting Lip Liner · Amazonian Clay Eyeshadow Palette · Caviar Tightline Eyeliner · Notorious Mascara Precisely My Brow (Cool Grey)

Frequently Asked Questions

The Real Secret

Notice what none of these looks are trying to do: turn back the clock. Not one of them is a costume of who I used to be. They’re clothes that fit the woman I am now — comfortable, put-together, and connected by that one red thread.

That’s the whole answer to what to wear to a high school reunion. Dress as the woman you already are. She’s the one worth showing up for.

Style has no expiration date — and neither do you.