How to Look Like a Boss at your High School Reunion

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The time has come, the time you’ve been looking forward to and/or dreading in equal measure. Your high school reunion, where memories of bad haircuts and worse clothes loom large.

So, how do you cut a rug surrounded by people you haven’t seen in years and who probably don’t remember you?


The first thing anyone notices is what you’re wearing, and first impressions matter. It doesn’t matter if you’re a billionaire playboy at leisure, if you roll up in ripped jeans and a stained shirt, you’re not doing yourself any favours. A high school reunion lets you make a second first impression, and there aren’t many opportunities to do that.

So spend a little cash on some good clothes. A tux and top hat will certainly stand out, but may be a little too dressy, so pony up for a good shirt, tie and slacks. Make sure they fit correctly. If you’re a scarecrow, wearing clothes that are too big could result in you getting lost. If you’re larger, wearing clothes a size too large makes you look shapeless and even bigger.

“Clothes should fit the body you have now; not the one you aspire to have. Sometimes people will buy clothes in smaller sizes, because they intend to lose weight. This is a faulty approach,” according to Robert van Tongeren from

For men, a nice shirt and tie, with slacks and shoes, not boots or sneakers. For ladies, keep jewelry to a minimum, with good heels and a classy dress.

Grooming and hygiene

Get a haircut. No arguments. Listen to your barber. It’s their job to make you look good and odds are they’re better at it than you are. Ask for their advice and follow it. Unless you’re a death metal rock god, keep your hair trimmed and controlled. If by some chance you are a death metal rock god, you probably already have a stylist whose entire job is keeping you presentable and on-brand, so this will be preaching to the choir.

When it comes to beards and other facial hair, again, talk to your barber. Not everyone can pull off the grizzled look, and even fewer can make the Gandalf look work. Again, generally speaking, less is more. Keep it tamed and under control by investing in a beard trimmer. According to Askmen, “facial hair can add definition to a soft face or ruggedness to a childish one.”

If you have any skin conditions, like acne or psoriasis, talk to a dermatologist or a pharmacist in advance. You don’t want a flare-up on the big night, so plan ahead. Most ointments or treatments are affordable and easy to use. If necessary, see your dentist beforehand for a quick teeth whitening session. Every little bit helps.


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It’s time to schmooze with people you haven’t seen for years.

If you have a Facebook or are active on other social media sites, Anna Borges recommends you scout out information and arrange to meet up with old friends ahead of time, “a quick hello to the old BFFs you’re excited to see will help you gauge what to expect and line up potential allies for when you arrive.”

You may already have added old friends to your Facebook or Twitter, so you should know some of their basic information, whether they’re married, if they have kids, or where they currently live. It’s not stalking, it’s fact-finding. Knowing little bits of information goes a long way to establishing good relations with people.

We like it when people take an interest in us. Again, don’t go overboard. Keep it simple, don’t mention their brief weekend trip to Missouri eight years ago or their kids graduation unless it happened recently.

It might be a stereotype to get liquored up to loosen up at social events, and sure, alcohol is the great equalizer socially, but Anna offers, “two rules to keep in mind: 1) Don’t use alcohol as liquid courage, and 2) Know your limit.” You don’t want to be the guy who punched out the running back at the reunion.

Another thing to learn is how to laugh at yourself. High school is a weird time for everyone, with multiple fashion and social faux pas committed on a daily basis. It’s a time to revisit past mistakes and remember where you came from. Don’t get annoyed or angry if it comes up, it doesn’t reflect well on you. As Dianne Gottsman of points out, “everyone has changed since your high school days, even you.”


A good entrance is key. Much like your clothes, if you pull up in a clapped out Jetta, it doesn’t look good. Once again, splash some cash and rent a limo for the evening. At Echo Limousine, our drivers are timely and they are always dressed sharp. We offer a reasonable range of prices, that are well within any customers means, and are consistently highly rated on multiple review sites.

You can get limo service to and from Chicago locations at any time of day with Echo Limousine. We provide private, personalized treatment to such notable spots as US Cellular Field, Soldier Field or First Midwest Bank Amphitheater in the suburbs and more.

Call us at (773) 774-1074 or click here to get in touch with us.

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