Note: Triple Aught Design sent this shirt for review.
Truth be told, I’ve been eyeing this Overland shirt for a very long time now. I love shirts that have modern touches in classic fabrics for rather niche uses. This is exactly that, a 100% Twill shirt, made for overlanding adventures — sign me up.
Since getting this shirt, I’ve been wearing it the moment the weather cools enough for it not to overheat me, and a few times when it was a touch too warm, and I’ve found that it’s a very easy wearing and comfortable shirt, which sits nicely between firm workwear, and something a little more put together. Is this like smart workwear? I am not sure. I am sure I like this shirt.

Materials
This is cut as a relaxed fit, 100% French Cotton Twill shirt, shown here in Olive. The material itself is 4.50oz — heavy but not overbearing. The two chest pockets are classic workwear flap pockets, cut rather large.

The buttons are classic Triple Aught Design, with a tubular flat lace system. This is one of the few touches which puts a modern spin on the shirt. There’s two hidden pockets on the inside left of the shirt as well.
The hem is cut straight, making this shirt look good untucked. It has sleeve straps to keep the sleeves rolled up, and a nicely sewn collar which keeps its shape and isn’t prone to falling flat.

As with everything I’ve received from Triple Aught Design, the materials and construction are well done and clean.
How it Wears

With items like this, I like to frame how they wear with what the intent for them is. Here’s the design intent:
Charting your course is just as important as leaving room for spontaneous readjustments to it. Made from 100% French Twill Cotton, our Overland Shirt is a streamlined travel staple updated with classic style, breathable performance and durability. Maintain your cool wherever the road may lead.
I’d sum that up as: classic looking adventure travel shirt. I think this shirt pulls it off well. A few things to note in bullet form before diving in further:
- Despite the description, I don’t find this shirt to be long enough for me to reliably tuck in. A large part of this is likely my abnormally long torso, so if you are in that boat, then know that it might not be long enough. It’s also boxy and so tucking it in can create odd folds in the fabric around the waist.
- I have been surprised at how well this shirt does breathe. It’s not an overly heavy fabric, and wearing it with a t-shirt under it, I found myself walking in warmer than anticipated temperatures, and while I was getting warm, I didn’t get sweaty.
- A key hallmark of a good travel shirt is that it doesn’t look like a creased mess either after washing or while sitting in a car. This material does very well here. It gets rumpled, but never unkempt, whether out of the washer, or after a day of sitting and lounging in the shirt. (All images here are with a few days of wear on the shirt.)
- The odd button placket system does have a practical effect, where I have found it keeps the shirt placket laying a little flatter than a shirt without that webbing stitched down it, all without the placket looking stiff (as it would if it were fused).

I’ll start with the looks on this, which I alluded to at the start: it’s a slightly more refined workwear look. Triple Aught Design notes that they essentially trimmed down the cut on this shirt, while keeping it a more relaxed fit. On me, the cut doesn’t feel overly relaxed, and I would characterize it more like a regular fit than the more common slim fits we are used to these days. The twill is classy looking without being delicate, and this helps keep it a little more versatile than pure workwear.

Inside hidden pockets.
I did find that the shirt moves well, and allows for plenty of articulation of your arms. As noted, the length on me is better for wearing untucked, than tucked, and the straight hem aids in the shirt looking clean when it’s not tucked in. Since this is a workwear shirt, leaving it untucked looks good when leaning into the overall aesthetic.

Moving over to the ‘how it works’ aspects, there’s a couple of things I want to call out:
- The collar is fantastic. They’ve done a great job keeping the collar casual looking, while not letting it get sloppy. So it looks soft, feels soft, but still holds its shape all day long. This is really nicely done.
- The sleeve tabs require the shirt to be rolled decently high on the arm. This isn’t something I am used to, however when I rolled them and secured them to walk home in hot weather, I found that it was a great length and kept me much cooler than anticipated. It’s about an inch and a half above my elbow when secured.
- I’ve found that the inside hidden pockets aren’t something I would typically use, and they add a bit of stiffness where they are sewn in — such that you can feel them as the shirt brushes past your body. I’m hoping these continue to soften with time, but I wouldn’t miss these pockets if they were removed. They would be great for travel if you needed to stash some cash, otherwise anything heavy would likely cause some odd draping on the material.
- I absolutely love the look, feel, and color of the material.
- The front pockets are positioned nicely, and are rather functional — I tend to actually use these types of pockets on heavier materials like this, and this shirt is no exception.
This shirt is very easy to wear, and very comfortable to wear. It pairs well with denim. It can work as an overshirt, or as a primary shirt as I have been wearing it. It keeps things casual, but looking a little more put together.
Overall

I am a fan of this shirt. It’s a nice layer for me when I am doing chores around the house, or darting out for errands. Keeping it easy and comfortable, without needing worry about my shirt at all if I end up carrying some boxes around, or run into someone on the sidewalk I wasn’t expecting to see, but wouldn’t want to look like a slob in front of.
This is a great explorer style shirt, which I am sure will find its way into my bag time and time again. Its design brief is for overlanding, and it seems like it would be right at home in a Defender 110 — modern or vintage.
