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Side view of office look with Ann Taylor silk knit top, Anne Klein floral print oblong scarf, Liz Claiborne pumps, Hermes collier de chien bangle, statement necklace (all own), wooden sport watch c/o Jord, and teal silk midi skirt c/o Lilysilk

What outfit to wear to a high school reunion in midlife depends on the location of the meeting. Read to get ideas for looks with pieces you have in your own closet for the location including tips on grooming, and being confident about yourself.

  1. Should You Dress like Back Then?
  2. How to Use Your Clothes to Convey a Message about You
  3. Take the Location into Account when Choosing Your Outfit
  4. Grooming Does a Lot for Your Look
  5. How to Impress at Your High School Reunion?
  6. How to Be Confident about Yourself
  7. What Are the Biggest Mistakes when Dressing for a High School Reunion?
  8. What Not to Talk about at a High School Reunion?
  9. Final Remark On Dressing for a Class Reunion


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Should You Dress Like Back Then?

By all means No.

Why? Trends have changed, and most likely your personal style changed with the lifestyle you lead now. For instance, my style had progressed from wearing old clothes from attics and cellars or bought on flea markets in the 1970s, to the 1980s’ power dressing – called Banker Style in West Germany.

Dress according to who you are today! High school is how many years ago? 20, 30, 35, 40? Eons, light years? Most likely they have self-adhesive name tags.

Furthermore, you most likely only remember the names of whom you liked/disliked back then. For the first you cared, and you prefer to see the backs of the latter anyway. The rest was below your radar screen; they were there, but invisible.

When your former class has met every year, or you and most classmates stayed in the same neighborhood, you grew “old” with each other. As a result, they have most likely no problems to recognize you. If you or they moved away, they may even not remember what you wore back then.


How to Use Your Clothes to Convey a Message about You …

… without having to talk. Keep in mind what you would like to talk about. It’s up to you whether you want to dress according to your leisure/weekend style or dress to impress. In the latter case, dress like you would dress for a work meeting. Such an outfit may lead to conversations about your job/career. The former could lead to chatting about your hobbies. It’s up to you. You choose.

When you were a stay-at-home mom and are now an empty nester, but don’t work, take the opportunity to dress up. Add a unique accessory that can function as an ice breaker. Cute shoes are always a good idea too. And don’t feel inferior to the women who work(ed). In today’s times, having been able to stay-at-home is a luxury most families can’t even afford (only for a while)! So be proud and feel blessed of having been able to raise your kids.

When you are (lucky to be) retired, dress up too. Make sure to add an accessory that is related to what you do now. It helps to get into a conversation. Necklaces, earrings, brooches, scarves and even belts are great options to do so. More on accessorizing with belts  and on  how to up your style with scarves.


Take the Location into Account when Choosing Your Outfit

The location may give you hints what to wear. If it is a dinner at a restaurant, some kind of loosely-defined cocktail attire is a good choice at an upscale place. If the restaurant is casual/rustic, take their usual dress code up a notch with a bit more glam. It’s a celebration after all! Well, call it a show! Yes, it’s all about high school.


purple cocktail dress for class celebration at an upscale restaurant
Calvin Klein purple drape and pleated dress, Hipstik pantyhose, Halftee, baroque colored pearl necklace closed with brooch, knitted shoes c/o Vivaia, and navy dial olive wrist band c/o Nordgreen watch.


Choose the shoes dependent on whether the party will be in the restaurant’s beer garden or in a reserved room. If it is outside go for ballerina flats or wedges. Otherwise, sandals or pumps are fine.

A meeting in the gym of your former high school indicates a casual setting. Most likely, they prohibit street shoes, and ask for clean non-marking shoes or sneakers. A pretty dress plus denim jacket with sneakers strikes a casual posh balance. When you love heels, wear fancy dance shoes.


printed dress with sneaker for a high school reunion in the gym
Victoria Victoria Beckham clothing print dress, Hipstik opaque tights, Puma sneakers, Hermes collier de chien bangle, Paloma Picasso sunglasses, Puma pendant necklace, and Nordgreen watch. Go for a bag that can hold your street shoes/sneakers.


Tip: When in doubt, wear a business casual outfit.


business casual outfit for a class reunion
Ann Klein blazer, Ethyl Clothes dark-wash jeans, snake-tail belt, Oliveo chambray button-down shirt, multiple strands of pearls, Hermes collier de chien bangle, Escada denim booties, and Nordgreen watch.


Grooming Does a Lot for Your Look

Make an appointment for a haircut the week before so your hair doesn’t look like freshly cut. If you dye your hair, do it in the week before.

Get an appointment for a blowout, and a manicure on the day of the reunion. However, have your eyebrows waxed at latest a day before. The beauty person might use too hot wax, and burn you. On the same day, there is no chance to cover a burn with concealer.

Needless to say, cover-up everything, e.g., age-spots with concealer, and make-up as needed. Use a primer prior to applying makeup so it looks more even. Go for a barely there makeup to look young and sophisticated.


… and yes, avoid fashion mistakes that make you look old.


How to Be Confident about Yourself

Recall there may be all those awkward situations like meeting your former bully, former high school sweetheart, your ex-boyfriend, or even ex-husband when you married your high school sweetheart.
Also it takes nerves when there is this one competitive person who always had to be the best, the most beautiful, sexiest,  popular, the most who knows what. Most likely that classmate still has this attitude. That person will have maxed out their credit card to dress in all upscale designer telling you that they became rich in the stock market, married a millionaire, won the lottery, … You get the idea.

Be confident, just find an excuse to go away. Restroom, refill, making a call, whatever excuse comes up your mind. Most likely that person has a terrible evening anyhow. Wearing these clothes with the price tags carefully taped on the inside so the pieces can be exchanged at Neiman Marcus or 5th Avenue the next day to “reset” the credit card.


How to Impress at Your High School Reunion?

Dress to represent the person that you are now, i.e. the person you have become. This way you come across confident about yourself. You achieved a lot, and have gone a long way from back then.

Get rid of your high school insecurities. Be a great listener. Talking the entire time about you can come across as trying to seem to be more than you are and/or insecure/unhappy about your achievements.


What Are the Biggest Mistakes When Dressing for a High School Reunion?

The worst mistakes when picking your class reunion outfit are:

  • Giving yourself a makeover. That’s like being in disguise.
  • Overdressing. You might come across as insecure.
  • Dressing like back in high school. It would make you look like a big failure.
  • Going on a diet because of the event. Instead wear heels and an outfit in dark neutrals with vertical lines (seams, stripes) to give the illusion of being slimmer than you are. Practice walking in heels, if needed.




midlife woman looking posh in a knitted silk top and silk skirt office outfit
Outfit inspiration for a dinner at a casual restaurant. Ann Taylor silk knit top, Anne Klein floral print oblong scarf, Liz Claiborne pumps, Hermes collier de chien bangle, statement necklace, wooden sport watch c/o JORD, and teal silk midi skirt c/o Lilysilk


What Not to Talk about at a High School Reunion?

The one thing you never should start talking about is your kids or grandkids. You have a life of your own, and yes, that not boring at all. Period.


Final Remark On Dressing for a Class Reunion

Enjoy the reunion and don’t envy anyone. They all tried their best to look like beautiful white swans.

Photos: G. Kramm

© 2013-2023 Nicole Mölders | All rights reserved

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