What to Wear to Your High School reunion

This post may or may not date me. But I will say that this conversation has come up more than once and so, needed to happen. So if, horror of all horrors, you find yourself realizing an entire decade has passed between your blossoming adolescence and the overhyped period known as your 20s, you’re likely dying to go back and blow everyone away and/or prove you’ve still got it. Which really (in addition to losing a few lbs.) all amounts to what you wear. Forget about if you’re still single, onto your third divorce or unemployed (hey, the economy sucks right?), look the part, get a cocktail and have a good time. Here’s how:

1. Relax. Stress is only going to make you break out, bite your nails, overeat or insert-whatever-bad-habit-you-have-here. And these are all the last things you want during your reunion. Take a second, breathe and realize if you’ve managed to survive High School (and the past 10, 20 or 30 years of your life) you’ll survive this evening too.

2. Assess the situation. Are you getting together for a casual picnic or an evening at a resort? Before having the what-to-wear panic attack, determine if the event calls for something casual or a little bit dressier.

3.Don’t try something new. And by new, I mean out-of-body experience-new. It’s O.K. to swipe on some lipstick or pile on a few extra baubles you may not normally wear, but if you’re not one to wear heels (or leather pants for that matter) this isn’t the night to try it.

4. Don’t try too hard. It’s obvious. It’s sad. People will see right through it. Stick to the classic rule by eliminating one accessory before leaving the house for an effortlessly chic, yet pulled together, look.

5. When in doubt, wear black. It’s classic and works for pretty much every occasion.


Try some cute leggings, heels and a nice top. If it’s chilly out a loosely fitted blazer also dresses up the look.

When in doubt, jeans, jeans, jeans. Paired with a nice top (I tend to stick to black) and heels, it’s goof-proof.

For happy hours or daytime events a flirty skirt or dress paired with boots or flats is the key to casual chic.

For cocktail attire…options are endless!

Have you been to a High School reunion yet? What did you wear??


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