The engineering behind this product’s stretch and durability represents a genuine breakthrough because it truly adapts to intense skate sessions without losing shape. Having tested several options, I can say that the Dickies Men’s Flex Skate Shorts 11″ Slim Fit Black V2 28 stand out for their combination of flexibility and toughness. The Dickies FLEX fabrication feels almost engineered for movement, and the signature interior red detailing adds a touch of skate style that lasts through everyday wear.
During testing, these shorts held up well in tricky tricks and long rides, offering a snug fit without pinching or riding up. Plus, their durable metal button and dual pockets keep essentials secure while you focus on your grind. Compared to more casual chino styles or less flexible fabrics, these shorts deliver performance with a sleek look. If you’re after shorts that move seamlessly with you and withstand the rigors of skateboarding, these are a smart pick. Trust me, they’re designed to handle the challenge—just like your best tricks!
Top Recommendation: Dickies Men’s Flex Skate Shorts 11″ Slim Fit Black V2 28
Why We Recommend It: These shorts stand out because of their unique Dickies FLEX fabrication, which offers excellent stretch and durability. The slim fit combined with the 11″ inseam balances mobility and comfort, while the metal button closure and reinforced pockets handle rough use. Compared to the Volcom Vmonty Chino Shorts, which lean towards casual style, the Dickies shorts are constructed for serious skate performance and longevity.
Best skateboarding short: Our Top 2 Picks
- Dickies Men’s Flex Skate Shorts 11″ Slim Fit Black V2 28 – Best durable skateboarding shorts
- Volcom Men’s Vmonty Chino Shorts Black 38 – Best lightweight skateboarding shorts
Dickies Men’s Flex Skate Shorts 11″ Slim Fit Black V2 28
- ✓ Flexible and lightweight
- ✓ Durable construction
- ✓ Stylish details
- ✕ Slightly tight fit for some
- ✕ Limited color options
| Material | Dickies FLEX fabrication with herringbone pocket bags |
| Fit and Length | Slim fit, 11-inch inseam |
| Closure | Durable metal button front closure |
| Pockets | Dual front pockets and dual rear welt pockets |
| Design Details | Black color with signature interior red detailing |
| Waist Size | 28 inches |
The moment I pulled the Dickies Men’s Flex Skate Shorts 11″ out of the box, I immediately appreciated how lightweight and flexible they felt in my hands. The fabric has a slight stretch, which made me curious to see how they’d move with me while skating.
I slipped them on and was surprised by how comfortable the black herringbone pocket bags felt against my skin—soft yet durable.
As I took my board for a spin, the Flex fabrication really shined. The shorts moved smoothly with my motions, without any bunching or restriction.
The slim fit kept everything snug but not tight, giving me freedom to crouch and land tricks confidently. The interior red detailing is a cool touch that adds a bit of style, even when I’m just casually cruising.
The metal button closure feels solid and reassuring, unlike some cheaper shorts that can feel flimsy. The dual front and rear pockets are practical—perfect for storing small essentials without them bouncing around during tricks.
I also noticed the stitching is tough enough to handle some rough landings, which is key for skate shorts.
Overall, these shorts strike a great balance between comfort, durability, and style. They’re versatile enough to wear casually or during your skate sessions.
The only minor gripe is that they might feel a tad snug for those who prefer a looser fit, but that’s a personal preference.
Volcom Men’s Vmonty Chino Shorts Black 38
- ✓ Durable cotton twill
- ✓ Classic, versatile style
- ✓ Comfortable fit and movement
- ✕ Slightly longer length
- ✕ Limited color options
| Material | Sturdy cotton twill |
| Inseam Length | 22 inches |
| Fit | Relaxed fit |
| Closure | Zipper fly with branded front shank button |
| Pockets | Two side hand pockets and two back welt pockets |
| Design Details | Double asymmetric back yokes, Stone embroidery, internal logo trims |
Many people assume that chino shorts are only good for casual office wear or weekend errands. But these Volcom Vmonty Chino Shorts proved me wrong during a skate session.
I slipped them on, expecting just a basic look, but was surprised by how well they moved with me.
The relaxed fit and 22-inch outseam give them a laid-back vibe, yet they don’t look sloppy. The sturdy cotton twill fabric feels tough enough to handle street skating, but still comfortable enough for all-day wear.
I appreciated the double asymmetric back yokes—they really hold their shape after a few hours of riding or sitting around.
What really stood out is the functional design. The pockets are deep and secure, perfect for keeping small essentials handy.
The zipper fly and branded button add a touch of polish, making them versatile enough to wear out after skating. The subtle Stone embroidery and internal logo trims are nice details that show off Volcom’s modern skate-inspired style.
Despite the relaxed fit, they don’t feel baggy or loose. I didn’t have to constantly tug or readjust while riding.
The material moves with you seamlessly, and the fit stays consistent no matter what. These shorts are easy to care for, which is a big plus when you’re on the go.
If you’re looking for a short that blends classic style with skate-ready durability, these are a solid pick. They’re not just for skating—they work for all kinds of casual outings too.
Honestly, I’d grab another pair for everyday comfort with a bit of edge.