Jockstraps

Born for support. Made for style.

The jockstrap has a surprisingly rich history. Invented in 1874 by Charles Bennett of the Bike Athletic Company in Chicago, it was originally designed to support cyclists — known then as “bike jockeys” — on the rough cobblestone streets of Boston. Nearly 150 years later, it’s become one of the most iconic and expressive pieces of men’s underwear in the world.

A jockstrap features an elastic waistband with a supportive front pouch and two elastic straps that run beneath the buttocks back to the waistband — leaving the back completely open. That signature silhouette is what makes it so distinctive.

Why choose a jockstrap?

💪 Maximum support — engineered to keep everything securely in place during sport or everyday wear
🔥 Open‑back design — that iconic cut that lifts, accentuates, and turns heads
🌈 Bold & expressive — from classic styles to daring prints and sheer designs, there’s a jockstrap for every personality
❤️ A community favourite — widely celebrated in the LGBTQ+ community as both fashion and sexy lingerie

Today, the jockstrap is worn as much for style as for sport — a statement piece that celebrates masculinity, confidence, and self‑expression. At Pineapple‑Wear, we think that’s worth celebrating.

Show up. Stand out. Own it.