The Best Fitting Trucker Hats for Men With Smaller Heads
(Updated 8/20/25): 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
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
3. Solo Palm Hat
- Minimalist beach-inspired style
- Subtle and stylish for travel or everyday wear
- Fits smaller heads without drowning your look
4. Dark Mountain Hat
- Bold mountain silhouette with contrasting linework
- Genuine leather patch sewn on for durability
- Available in Small and M/L sizes in both the 115 and 112
How 115 Compares to the 112
The Richardson 112 is a classic for a reason—mid‑profile with just the right structure and roominess to feel instantly familiar. The 115 sits lower on the head for a snugger, sleeker fit—perfect if you want something that feels a little more streamlined.
We now offer both the 112 and 115 in small sizes—which means the diameter is scaled down, not necessarily the crown profile. The small size mostly affects the circumference (lowers the fit for smaller heads), while the profile shape (medium‑ for the 112, low‑ for the 115) stays the same.
So whether you want that traditional mid-profile feel of the 112 or the more fitted look of the 115, both are now easier to wear for smaller head sizes.
Explore both the 115 and the 112
New Additions: Small Size Richardson 112 Hats
We’re excited to now offer small size Richardson 112 hats. These are a perfect option if standard trucker hats run too large. Unlike the 115 small, which combines a smaller diameter with a low profile crown, the 112 small keeps the traditional medium profile fit while adjusting the diameter for a smaller head size.
Featured Designs:
– West Pine – A rugged, outdoors-inspired patch design that pairs well with the classic trucker look of the 112.
– Mosaic Wings – A modern geometric patch that makes a bold statement while keeping the same great fit.
Shop the Mosaic Wings Small Trucker Hat
These are just two of the designs now available in the 112 small. You’ll find more options in our shop, but if you’re looking for a trucker hat that finally fits right, these are a great place to start.
Small vs. Standard Sizing (112 & 115)
On both the Richardson 112 and 115, the profile stays the same—112 is mid-profile, 115 is low-profile—but the band size and overall fit change.
Size labels
– 112 Small / 115 Small: fits about 6 1/2–7 1/4 in fitted sizes
– 112 OSFM / 115 M/L: fits about 7–7 3/4 in fitted sizes
Quick picker
– If a trucker hat wobbles when tight or sits on the last 1–3 snaps, go with Small
– If you’re usually in the middle snaps on standard truckers, the OSFM (112) or M/L (115) is the better choice
Fast measure
– Measure just above your brows and ears
– Under ~22 in (56 cm): usually Small
– Above ~22 in (56 cm): stick with OSFM (112) or M/L (115)
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.
