What to Wear for a High School Reunion

Homecoming is right around the corner and I just received notice for upcoming reunions at my High School Alma mater.   I survived both my 10 and 20 year High School reunions.  I stressed about my outfit, hair, which events to attend, and taking a date or going alone.

Here are my tips of what to wear and how to reduce stress to be comfortable and CONFIDENT!

10 Year High School Reunions are usually the first time seeing people since graduation.  Sure, you may keep in touch via Facebook, but this is the reunion to show off your grown-up, successful self!  The 10 year event can be very catty and judgmental.  The old high school cliques start forming as soon as people arrived.  I am glad that I attended, but it was a slow, painful beginning.

My 10 year reunion had a Friday night cocktail event and Saturday dinner (the main attraction).  More schools are coordinating full weekend events to increase attendance from the out of town graduates.  I bought tickets for both night events with a plan to skip Saturday if the first event was a nightmare.

Dress for the Event and Location – While Friday was called a cocktail party, and it was really a Happy Hour in disguise.  I overdressed in a designer cocktail dress, but really wish I wore something more casual.  A flattering top & skirt or casual dress would have fit in perfectly.  Everyone around me was wearing jeans or nice skirt/pants.  I should have paid attention to the venue and realized it was not some super fancy, posh cocktail hour.

Suggestions (In order of Casual to Formal):

• Nice tee-shirt, dark jeans, and flats, low heel or wedge shoes
• Maxi dress with flats or sandals
• Simple top or blouse and skirt with cross body handbag
• Simple casual dress and strappy heels
• Blouse and dress slacks with heels
• Cocktail dress and high heels
• Floor length evening gown
• Cinderella style ball gown, complete with golden carriage – Only if the event is Black Tie Formal held at a Castle

 

 

 

 

 

 

Avoid too-tight and too-short outfits.  There were way too many women trying to prove how hot and sexy they still are, and it just looked desperate.  These are also the same women tripping in their (slick on the bottom new) too high heels and kept pulling at the hem of their skirt when sitting.  Basically they were so focused on their uncomfortable outfit they clearly did not enjoy the event.

My Friday cocktail dress would have been perfect for the dressier Saturday night dinner.  Crap, I already wore it.  This would have been the time to switch Saturday night outfits, but I did not.  Once again, I showed up extremely overdressed for the reunion dinner.  Cocktail night did reinforce that going alone was better for me than bringing a date that I barely knew.

Test run your outfit – Wear the complete outfit including shoes and accessories around your house before the event (at least a few days, so you have time to change anything wrong).  Can you comfortably sit, walk, and move in your outfit?  Look at yourself from multiple angles.  This is the time to determine if those shoes pinch or the straps are too loose.  Test runs are the time to determine if you need a strapless or special bra before the event.

Honestly, does this style reflect YOU?  Would your friends recognize you in your outfit?  Do not change who you are!


Once you have the full outfit, keep everything together so you do not waste any time hunting for any item while you are getting dressed.  A little preparation the day or 2 before will ensure everything is clean to reduce any risk of last minute fashion melt-downs.

Be Confident – A comfortable, stylish outfit is a great foundation for the event.  Catch up with old friends, find out that you have things in common with people, make new connections, and enjoy yourself!

20 Year High School Reunions are so much easier!  People are fatter, balder, and much more relaxed that at the 10 year reunion.  Again, there was a Friday night happy hour at a local bar, Saturday family picnic, and Saturday night (buffet) dinner & drinks.

The same outfit suggestions & test run apply for the 20 year, as the 10 year reunions.  It is far more likely that the 20 year will be casual, so dress accordingly.  The people that attended the 20 year Saturday night reunion came for fun, very few folks showed up trying to impress anyone.  I wore a knee-length dress with comfortable heels, so I was able to walk around and mingle all night.  Most of the guys wore nice jeans, and a few wore dress slacks.  One friend of mine wore a jacket and tie, because that is what he is comfortable wearing. Since it was fairly casual, women wore maxi dresses, skirts, jeans, and sun dresses with flats, sandals, and low heels.

I genuinely had fun at my 20 year reunion.  I reconnected with some old friends, and finally made a connect to folks that shared the same experiences with me all those years ago.