The Undie 100: Celebrating 100 Skydives in Style

Table of Contents

Skydiving has its traditions, and one of the most memorable (and hilarious) is the “Undie 100.” For those who don’t know, when a skydiver reaches their 100th jump, it’s tradition to celebrate by jumping in their underwear. Yep, you read that right—no fancy jumpsuit, no sleek gear… just you, your rig, your friends, and your undies at 13,000 feet.

This week, I officially hit that milestone—and I couldn’t have asked for a better way to do it.

Why the Undie 100?

Skydiving is full of milestones: first jump, A license, first solo, first big-way… but your 100th jump is special. It’s where you start to feel less like a “new jumper” and more like part of the family. The “undie jump” is about letting loose, celebrating how far you’ve come, and not taking yourself too seriously.

It’s a reminder that at the core of skydiving, beyond the licenses, ratings, and achievements—it’s about fun, community, and making memories that last a lifetime.

Skydiving

Flying Free (and Freezing a Little)

Jumping in underwear is definitely a unique experience. The rush of cold air hits instantly, but so does the laughter. There’s something freeing about stepping out of the plane with nothing but your gear and a huge smile, surrounded by friends who are cheering you on (and probably laughing with you the whole way down).

Sharing It With Friends

What made it even better was being able to share the jump with friends. Milestones mean so much more when the people around you lift you up—literally and figuratively. Every cheer, every high five, and every laugh under canopy made this moment unforgettable.

Looking Back—and Ahead

Hitting 100 jumps feels surreal. I still remember my first jump, the nerves, the shaky legs, the wide-eyed “did I really just do that?!” feeling. Now, at 100, I feel stronger, more confident, and more in love with the sport than ever.

And while the Undie 100 is a hilarious milestone, it’s also a reminder: the journey doesn’t stop here. Every skydive is another opportunity to grow, to learn, and to have a blast in the sky.

Here’s to the next 100—and all the laughs, lessons, and milestones along the way.

Blue skies (and maybe pants next time),
—Brooke
– B-Licensed Skydiver & Manifest Coordinator

Read More

Skydiver Traditions: The Little Rituals That Mean Everything

Skydiving isn’t just about the freefall, the canopy ride, or even the adrenaline rush. It’s also about the community and the traditions that make every jump feel like part of >>

August Put New Names in the Sky

August paired beautiful early-morning views with two milestones that meant even more to our drop zone. We watched Maurice and Kaitlyn complete the work required for their USPA A Licenses, >>

Finding My Place: Stepping Into the Coach Course

When I first signed up for the Coach Course, I’ll be honest—I was nervous. The idea of being evaluated, tested, and stepping into a bigger role in the skydiving community >>

The Undie 100: Celebrating 100 Skydives in Style

Skydiving has its traditions, and one of the most memorable (and hilarious) is the “Undie 100.” For those who don’t know, when a skydiver reaches their 100th jump, it’s tradition >>

July Put a Different Mission in the Air

July brought an unexpected change to the rhythm at Skydive Colorado Springs. With firefighting crews operating from the Penrose airport in response to the Aspen Acres Fire, we stepped back >>

Back to Basics: How Izzy Wing’s Canopy Course Felt Like Learning All Over Again

Sometimes, skydiving surprises you—not with the adrenaline, but with how much you still have to learn. I recently took Izzy Wing’s canopy course, and let me tell you… it felt >>