The Best Fitting Trucker Hats for Men With Smaller Heads

The Best Fitting Trucker Hats for Men With Smaller Heads

Finding a trucker hat that actually fits well when you have a smaller head can feel like chasing shade in the desert. Most are just too big, too tall, or too stiff. At Outer Wings, we know that fit matters just as much as style—especially when you're wearing your hat day after day, whether you’re hiking alpine trails or just grabbing coffee in a mountain town.

That’s why we carry one of the most versatile low-profile hats out there: the Richardson 115. It offers a dialed-in fit for guys with smaller heads, and we offer it in both Small and M/L sizes for that just-right feel.

This guide covers everything you need to know to finally find your perfect fit, including the best Outer Wings leather patch trucker hats available in the 115 and how they compare to other popular styles.


Why Most Trucker Hats Don’t Fit Smaller Heads

Let’s start with the basics. Most standard trucker hats are built on high-profile or mid-profile frames (like the Richardson 112), which sit higher on your head and often feel oversized if you have a smaller or more narrow head shape.

Here’s what makes the Richardson 115 different:

  • Low profile design: It sits closer to your head for a clean, tailored look.
  • Slightly smaller crown: Doesn’t overwhelm your face or create a mushroom effect.
  • Available in Small and M/L sizes: So you can actually choose what fits best.
  • Pre-curved bill and structured front: Keeps the shape, without looking boxy.

This combo of details makes the 115 ideal for men who want a great-fitting, high-quality trucker hat that still holds up in the outdoors.


Best Leather Patch Hats on the Richardson 115

Outer Wings designs each hat with purpose: adventure-ready, mountain-inspired, and subtly stylish. If you’re looking for a custom leather patch hat with a solid fit for smaller heads, start here:

1. Lost Pine Hat

  • Compass and pine tree design
  • Circle leather patch on low profile trucker
  • Available in Small and M/L sizes

Shop Lost Pine

Side view of the Lost Pine Hat in Caramel/Black, showcasing the breathable mesh back, structured profile, and adjustable closure. The hat includes a hand-stitched leather patch with a compass and pine trees design, perfect for those who love the outdoors.

2. Tidal Wave Hat

  • Ocean wave design on real leather
  • Genuine Colorado-made patch sewn with white thread
  • Small and M/L available in multiple colors

Explore Tidal Wave

Side view of the Tidal Wave Leather Patch Hat by Outer Wings in Heather Grey/Charcoal, highlighting the structured design, mesh back, and adjustable SnapBack closure. A rugged yet stylish outdoors hat for all your adventures.

3. Solo Palm Hat

  • Minimalist beach-inspired style
  • Subtle and stylish for travel or everyday wear
  • Fits smaller heads without drowning your look

See the Solo Palm

Side view of the Solo Palm Leather Patch Hat by Outer Wings in Charcoal/Black, showcasing the breathable mesh back, structured profile, and adjustable SnapBack closure. A stylish and durable outdoors hat for all adventures.

4. Dark Mountain Hat

  • Bold mountain silhouette with contrasting linework
  • Genuine leather patch sewn on for durability
  • Available in Small and M/L sizes

Grab the Dark Mountain


How 115 Compares to the 112

While the Richardson 112 is an industry favorite, it’s better suited to medium or larger heads due to its:

  • Mid-profile fit
  • Taller crown
  • More volume overall

If you've ever worn a 112 and felt like it just wasn't quite right, the 115 may be the fix. It's also worth noting that the 115 still gives you that classic trucker look—just in a more streamlined, comfortable version.

Check out our Richardson 115 Hats for more options that suit smaller heads.


Eco-Friendly and Built to Last

Each Outer Wings hat is handcrafted using:

  • Veg-tanned real leather patches, laser-engraved and hand-sewn in Colorado
  • Durable cotton/polyester blends with mesh backs
  • Stitched details for long-term wear (no cheap glue here)

They’re perfect for anyone seeking eco-friendly outdoor hats that look good at elevation, by the coast, or on the road.


Q&A: Finding the Right Trucker Hat Fit

Q: How do I know if I need a Small or M/L?
A: If most trucker hats feel too deep or stick out on the sides, go Small. If you’re in between, try both—our 115s offer flexibility thanks to the snapback.

Q: Are your leather patches real leather?
A: 100%. We use veg-tanned leather, which looks better with age and handles heat and sweat like a champ.

Q: Can I wear these for outdoor activities?
A: Absolutely. The mesh backs and pre-curved visors make them ideal for hiking, road trips, or just relaxing in the sun.

Q: Will these hats work for women too?
A: Definitely. The smaller sizes make them a popular option for women seeking leather patch trucker hats with a lower profile.

Q: Are there other low profile options besides the 115?
A: Yes. We also offer low profile styles in some Flat Bill Hats and Rope Hat Snapbacks.


Final Thoughts

Not every head is the same. That’s why Outer Wings offers the best trucker hats for men with smaller heads in styles that actually fit—without sacrificing quality, style, or performance.

Whether you’re chasing trails in Colorado or catching sunsets by the coast, our Richardson 115 leather patch hats deliver a better fit and better feel from day one.

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