What to Wear to a Casual Reunion : Outfit Ideas

Dear Deborah,

I’ve just received an invitation to a 30th class reunion, and I’m panicking about what to wear. It’s being held at a local bar, and the invite says “dress casually.”  I’m thinking that might mean jeans, but I’m also worried jeans aren’t dressy enough? What do you suggest to wear to a casual reunion? Thanks, Lynn

Hi Lynn,

These days, a class reunion is often a casual affair held in a basement, at a community hall,  a local bar, or in the high school gym.  These types of venues don’t require you to get too dressed up, however when you haven’t seen someone for many years; you want to look modern and stylish.

Here are some ideas for what to wear to a casual 30th class reunion to look relaxed, but classy.

Bootleg jeans and ruffle blouse over 40

Look Vibrant in a Colorful Blouse + Jeans

Even though your class reunion is casual, it’s not an everyday event. It’s a special occasion, and you want to put in a little extra effort. In other words, you don’t want to look like you’ve dressed to dash out to the grocery store for milk.

If you want to keep things at the most casual end of the casual spectrum, start with a pair of well-fitting jeans in a current style. Choose a cut that flatters your body. A classic dark wash is dressier than a lighter wash or a pair that is faded, whiskered, ripped, or distressed. Here I’m showing bootcut jeans that are classy and especially flattering for pear-shaped gals.

Think twice about wearing a black top. No matter how pretty it is, black is harsh when worn close to an over-40 face. Instead, a pretty and modern blouse in a complexion-flattering color like pink, peach, or coral will help you look youthful and vibrant. While I can’t guarantee it, there’s a good chance that everyone will tell you you haven’t aged a bit.

Also, pay attention to your accessories. Trendy accessories help express your unique style and show everyone that you’re not stuck in the past.


White Jeans and blue top for women over 40


Look Fresh and Modern in White Jeans + Bright Top

White jeans are a rung up from blue jeans on the dressy ladder. Not only do they make a casual outfit look more expensive, but white jeans are easy to style.

One of my favorite style recipes is to wear white jeans with a bold colored top. For example, bright blue with white jeans is very easy and fresh in spring and summer.

Wear nude shoes or sandals with your white jeans. Because they’re similar in color to the jeans, it creates a lovely, long line, making you appear tall and elegant. You can wear any kind of heel, but a block heel such as the one I show above is perfect if you’ll be spending a lot of time standing around greeting old friends.


Black pants for a class reunion

Look Successful in Black Pants + Great Accessories

If you want to look casually chic, then your go-to look would start with a pair of black pants. They read dressier than jeans (blue or white), but you can keep them grounded with casual shoes. A low-heeled pair of cute sandals is a good choice.

Black pants may be a staple in your wardrobe, but if you have had them for years, you’ll likely need to toss them out and buy an updated pair.  If they are worn, pilled, or simply the same ones you wore when Obama was first in office, get rid of them!

The most modern black pant these days is a skinny leg or a straight leg pants with an ankle crop. These are a fantastic backdrop to a pretty blouse. For a moneyed look, you can’t go wrong with a black and white blouse and black pants. Black and white are always a sophisticated mix.

As for accessories, they not only have the power to make a good outfit great, but they speak volumes about your style and personality. You don’t have to pile them on – in fact, unless you have a creative style personality you probably don’t want to pile them on – but one or two well-chosen accessories that are the best quality you can afford can make you look like a million bucks. (Even if you don’t make a million bucks. LOL)


What to wear to a reunion over 40

Look Pretty in a Dress

Some gals are dress gals, and even though the venue is casual, you may still want to wear one. I say, ‘Go for it!’ More than anything you want to look confident and if wearing a dress will make you feel confident, then a dress it shall be. You’ll never go wrong with a wrap dress which is always appropriate casual or dressy.

There are plenty of cute, casual dresses to choose from. I do recommend (again) that you think about color; a dress in a light or bright color is less severe than a dark color, and a pretty print such as a floral or geometric can be fun and playful.

Keep in mind that you probably don’t want to be standing around all night in high heels, so try a block heel, wedge, or kitten heels if you prefer a little height. Next, to flats, these are the most comfortable shoes for a casual class reunion.


Are you going to a casual class reunion this year? I’d love to hear about it.

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17 thoughts on “What to Wear to a Casual Reunion : Outfit Ideas

  1. Would a solid black jumpsuit, sleeveless low cut back, and knotted front top, with a wide snake print belt with matching flat sandals, be okay?

  2. I’m going to my 55th reunion. The dress is casual, so this email is very timely for me. My only question is if you have any different suggestions for women over 70.

    1. Hi Sue, I’d suggest the same thing for a 70-year-old for a casual reunion.. a nice pair of pants and a pretty blouse, or a pair of pants and a cute top and a casual jacket..or you could wear a simple dress.
      Something classic in a modern color or with a stylish detail is always appropriate. Cheers, Deb

      1. I’m going to my 45th class reunion, which will be casual this time. So you said we an r modern colors and styles. Can you please give examples if you don’t tell us what those are? Thank you

  3. Can you imagine my 60th class reunion is in Sept? When I graduated in 1954, I was a hip, young chick and a fashionable one. Then I graduated from college with a fashion degree. But now, how do I dress for this big day in my life? I am still very fashion minded and try to stay up to date. I’m 78 “young” and want to look young and fabulous. Help. (Funny how all fashion mags are for 50 years olds)

  4. These are both great outfits! However, neither fit my situation. My class reunion is in August when a jacket would be too hot, as suggested. The venue is too casual for a dress. What do you mean?

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