What to Wear to a High School Reunion (Chic & Casual Outfit Ideas for Women 40+)

Walking into a high school reunion can be downright nerve-wracking. Of course you’re excited to see old friends, but let’s be honest—there’s also that little voice in your head saying, “I want to look fabulous. I want to look healthy. I want to look vibrant, successful, and yes… warm and friendly too.” The big question is: how do you pull all that off in one outfit?

The good news is, it doesn’t have to be complicated. Most reunions these days are casual affairs, often held in restaurants, pubs, or community spaces. That means you can skip the sequins and stilettos, but you also don’t want to look like you just dashed in from running errands. The sweet spot is chic, comfortable, and confident—and I’ve got outfit ideas that will help you get there.

1. Jeans + Blazer = Effortless Cool

A pair of dark, well-fitting jeans instantly looks put-together, especially when paired with a blazer. Add a silky tank or blouse underneath, and finish with heels, ankle boots, or sleek flats. It’s casual enough to feel comfortable, but polished enough to say, “Yes, I’ve still got style.”

2. Midi Dress Magic

If you’d rather wear a dress, go for a midi. It’s flattering, easy to move in, and feels feminine without being overly extravagant. Choose a style in a solid color or a subtle print and pair it with block heels or wedges. Toss on a denim or leather jacket if you want to keep things relaxed. This is an excellent option if your reunion runs from day to evening.

3. The Jumpsuit Alternative

A jumpsuit is a one-piece garment that exudes modern confidence. A belted or tailored jumpsuit with cropped legs is sophisticated yet understated. Pair it with wedges or heeled sandals and simple jewelry. Bonus: You won’t have to stress about mixing and matching.

4. Elevated Casual Pieces

If the invite says “casual,” don’t interpret that as “sloppy.” Instead, think elevated basics. Tailored ankle pants with a patterned blouse, or straight-leg jeans with a pretty top and statement necklace. A little structure in your outfit goes a long way toward looking current and pulled together.

5. Slightly Dressier Option

If your reunion is at a nicer venue, such as a country club or banquet hall, consider dressing just a touch dressier. Wide-leg trousers and a silky blouse, a chic wrap dress, or a sleek blazer with dress pants all strike the right balance. The key is sophistication without appearing as though you’re heading to a boardroom or a cocktail party.

Finishing Touches That Matter

• Shoes: Choose comfort without sacrificing style. Block heels, low kitten heels, wedges, chic flats, or even polished sneakers (if the vibe is right) will let you mingle with ease.
• Accessories, such as earrings, a bracelet, and a stylish bag, can elevate even the simplest outfit.
• Hair & Makeup: Think fresh and polished, not prom night. Soft waves, a good blowout, or a sleek ponytail paired with natural makeup and a pop of lipstick will keep you looking confident and approachable.

What Not to Wear to a High School Reunion

It’s not about impressing people with an over-the-top look. Steer clear of anything too revealing, too young, or too dated. Overly distressed jeans, anything glittery from head to toe, or clothes that make you feel uncomfortable are best left in the closet. The point isn’t to relive your high school years—it’s to celebrate who you are now.

Remember, the best outfit for a reunion is one that feels like the best version of you. Whether that’s chic jeans with a blazer, a flowy midi dress, or a modern jumpsuit, wear something that makes you feel vibrant and at ease. Pair it with a big smile and your favorite lipstick, and you’ll be ready to turn heads for all the right reasons.

FAQ

Can I wear jeans to a high school reunion?
Yes! Jeans are excellent for most casual reunions. Just style them with a blazer, blouse, or great accessories so you look polished.

What colors work best?
Choose shades that flatter your skin tone and feel modern—jewel tones, chic neutrals, or soft pastels, depending on the season.

What’s the best way to look stylish but not overdressed?
Stick to updated classics. Dark denim, a blazer, a midi dress, or tailored pants paired with the right shoes and accessories will keep you chic without looking like you’re trying too hard.

How do I feel confident walking in?
Wear something that fits well and makes you feel comfortable. Confidence comes less from the clothes themselves and more from how comfortable you feel in them.

Meet the author

Deborah Boland

Deborah, a former Fashion & Lifestyle TV host and Image Consultant, understands the style challenges women face in their 40s, 50s, and 60s. As the founder of Fabulous After 40, she helps women tweak their chic and embrace fashion with confidence—so they always look and feel amazing.

Learn More About Deborah Explore Her Latest Posts