What to Wear to Your High School Reunion: Outfit Ideas

A screenshot of text messages discussing high school reunion styling; Julia Gall and a friend at their high school reunion — (Image credit: Julia Gall)

High school reunions are a very polarizing event, either met with dread or glee. Some people are thrilled to dive back into that awkwardness; others avoid it like the plague. I personally live for benign social experiments, so when my Class of 2005 reunion was slated for the fall of last year, I jumped at the opportunity to attend.

In preparation for such a milestone, my high school friend group chats lit up. Among the flurry of when/where/who questions was also: “What are you going to wear?!” This is a valid concern, since, unlike a wedding or funeral, there isn’t really a dress code for reliving high school dynamics in an emotionally-charged three-hour cocktail party filled with people you may have completely forgotten about.

a screenshot of texts discussing what to wear to a high school reunion — The high school group chats were lit up with urgent outfit deliberation for packing purposes.

Overall, a reunion is meant to be fun for all, but I understand how it can still trigger anxiety depending on your personal experience during this time in your life. As the anointed Best Dressed female of my school’s Class of 2005, I’m definitely not qualified to give advice on healing adolescent trauma, but I believe it’s within my expertise to help you figure out what to wear to reunite with this chaos. Here’s the wisdom I can impart after having survived my first, last, and only high school reunion.

Do: Play it Relatively Neutral

Julia Gall — My childhood bestie Kristen and I, putting our "sexy sweater and jeans" reunion uniforms to work.

As a fashion lover, I absolutely love any excuse to create a major sartorial moment, and don’t discourage anyone from dressing up to their heart’s content, I would say a high school reunion is the time to just be yourself, in whatever capacity that looks like for you. It’s disorienting enough to recognize people you may have completely forgotten about, so a wildly distracting outfit just adds to the overwhelm of the event itself.

My immediate thought was to do a “sexy sweater” and jeans—now, I don’t mean anything scandalous, but, instead of the usual boxy knits I’m always in for winter, I chose a loose Sézane cardigan in a pop of red that I’ve worn for date nights. I offset it with baggy jeans and loafers, to truly balance the feminine top with a “nothing to see here” vibe. I felt confident and comfortable, which is key for an event that requires so much social energy.

Sézane

Gaspard Cardigan

Reformation

Florie Twist Front Sweater

AGOLDE

Low Slung Baggy Jeans in Libertine

Levi's

Low Loose Women's Jeans

Margaux

The Marlowe Loafer

Charles & Keith

Arwen Tweed Diamond-Quilt Braided-Strap Shoulder Bag

Don’t: Flex Too Hard

While it’s tempting to depart via helicopter like in Romy & Michelle’s High School Reunion to flex on all of your high school enemies, I think it’s a lot cooler to just take things down a notch. Boasting success might be tempting, but don’t max out your card on a new bag and outfit just for this occasion. It’s simply not worth it. Live your truth.

Do: Lean Into School Spirit

My dear friend and key organizer of our class’s reunion, Scott, mentioned he was looking for a bright green sweater to wear to represent our school colors, but couldn’t find the right one on short notice. I think it’s cool (and not corny) to have a considered nod to school spirit with a rugby shirt, cricket sweater or even elevated track pants in your school’s color. And maybe there’s even a way to sneak in a hoodie or tee (not sweatpants, though) from that time period to play into the nostalgia. Some quick thoughts: styling under a blazer or leather jacket with jeans and a loafer or a slip skirt with boots, to keep the overall look still quite polished.

Lauren by Ralph Lauren

Cable-Knit Cotton Cricket Sweater

Superdown

Sashia Polo Top

Reformation

Julien Poplin Pant

Mother

The Team Spirit Jacket

Adidas x Wales Bonner

Knit Top

Lisa Says Gah x Relax Lacrosse

Miracle Mesh

Don’t: Relive the Era

Julia Gall images from high school — Some of my greatest outfit hits from the '00s—but not to be repeated in front of the same audience.

As tempting as it may be, especially in light of the 2016 revival, I would steer away from resurrecting old fads or even actual outfits from high school. Even though 20 years is usually when trends cycle back around as “vintage”, I think it’s perfectly fine to keep to your present-day style. You’re already entering a time warp so I vote for putting together a nostalgic playlist over a nostalgic outfit.

Do: Have Fun and Don’t: Overthink It!

a picture from Julia Gall's high school yearbook; julia gall and a friend at her high school reunion — My friend Vennedick and I—"Best Dressed" of our class (according to our yearbook), then and now.

High school reunions bring up all sorts of feelings, both wistful and traumatic. No one should feel pressured to relive any of the negative, but I would encourage attendance only if it feels fun to check in with people you may literally never see again. Be cute, be yourself and you’ll be ready to ride the completely disorienting wave of a high school reunion. Cowabunga!

Julia Gall is a creative consultant, stylist, and writer. She is the former Style Director at Marie Claire where she covered all things fashion, as well as styling tips, wardrobe upkeep and sustainability.