Why Trucker Hats Are Still the Best Hat for Men
Some trends fade fast. Trucker hats? They’ve stuck around for decades and there’s a reason for it.
When it comes to men’s hats, nothing else checks all the boxes like a well-made trucker hat. They’re breathable, comfortable, built for real use, and if you pick the right one, they look good without trying too hard. Whether you're navigating a trail or a weekend in town, the right trucker hat doesn’t just top off your look... it works.
At Outer Wings, we’re not trying to reinvent the trucker hat. We’re just doing it better — with genuine leather patches, premium Richardson builds, and clean, subtle style.
Here’s why they still win.
1. They're Built for Real Life
Trucker hats aren’t fragile or fussy. They're made to handle sweat, sun, dirt, and long days. With mesh backs and structured fronts, they hold their shape and stay breathable even when temps rise.
The right trucker hat wears well on a hike or at a brewery patio. It’s your do-it-all, go-anywhere cap and it doesn’t care if you’ve had it for one week or five years.
2. They Actually Fit
No two heads are the same. That’s why we use multiple Richardson styles, because fit matters. Whether you like a snug low profile or a roomier mid-profile, trucker hats offer a flexible, comfortable fit that other hats can’t match.
- Richardson 115: low profile, closer fit
- Richardson 112: mid-profile, classic crown height
- Richardson 168: high profile, flat bill, structured front
No matter your preference, there’s a trucker that fits you and your style.
3. They Get Better With Age
Especially when they feature a leather patch.
At Outer Wings, every patch is laser-engraved on real veg-tanned leather and sewn by hand; not heat-pressed, not glued. The result? A hat that only looks better with time. The leather softens, the fit molds to you, and the hat becomes yours in a way fast-fashion caps never do.
Three Trucker Hats That Prove the Point
If you’re ready to wear something that works just as hard as you do, here are three standout options from our collection:
American Flag Hat – Clean and Patriotic
Built on the Richardson 115, this one’s a fan favorite. The low profile fit hugs your head without riding high, and the hand-stitched 1776 flag patch keeps the message simple: proud, not loud.
- Real leather patch featuring stars and stripes
- Breathable mesh and pre-curved visor
- Low profile trucker hat fit
👉 Shop the American Flag Patch Hat
Mountain East – Modern and Rugged
Looking for a flat bill hat that doesn’t scream hype? The Mountain East is stitched on the Richardson 168, a seven-panel trucker with a flat brim and taller crown. It’s a clean, structured hat that wears just as well at a trailhead as it does in town.
- High-profile fit with flat bill and snapback
- Sturdy materials with clean mountain leather patch
- Our pick for bold style and long days outdoors
👉 Shop the Mountain East Trucker Hat
Driftline – Laid-Back and Adventure-Ready
The Driftline sits right in the sweet spot. Built on the Richardson 112, it’s a mid-profile hat with a relaxed curve, structured front, and breathable mesh. The linework river patch is subtle, simple, and quietly cool.
- Mid-profile fit with balanced proportions
- Mesh back, cotton/poly blend front
- Works with nearly anything you wear
👉 Shop the Driftline Trucker Hat
Where Trucker Hats Still Belong (Everywhere)
- Camping near the Tetons? Grab the Driftline or Mountain East.
- Running errands in town? The American Flag Hat brings casual pride.
- Climbing, grilling, working, or hiking? There’s a trucker for it.
Need to see more options?
- Check out more Trucker Hats
- Browse our collection of Flat Bill Hats
- Need a Low Profile Hat?
- Shop our Collection of Mountain Hats
Common Hat Questions
What’s the best type of trucker hat for all-day wear?
The Richardson 112 is a great mid-profile option, while the 115 sits closer for an athletic feel. If you like a taller crown and flat bill, go with the 168.
Why choose leather patch trucker hats?
They offer the structure and breathability of a great trucker, but the leather patch adds a rugged, premium finish that just gets better over time.
What’s the difference between low profile and mid-profile trucker hats?
Low profile hats (like the 115) sit closer to your head. Mid-profile (like the 112) have a bit more front height. It’s all about how you like your fit.
Don’t Overthink It — Trucker Hats Still Win
If you're looking for one hat to take you from a trail to the taproom and still look good at the family BBQ. It’s a trucker hat! And at Outer Wings, it’s a leather patch trucker hat built for wherever you're headed.
Before you go...Check out:
👉 All Trucker Hats
👉 Flat Bill Trucker Hats
👉 Low Profile Trucker Hats
