Escape Plan
The Fall Outfit Driven By Classic Cool
Inspired by the enduring ease of midcentury icons, this fall look is for the kind of weekends when the drive is slow, and the style is effortless.
Style doesn’t have to shout to be heard. There’s a quiet power in simplicity, a kind of mastery that’s not about the latest trend on TikTok but about how it all comes together.
I’ve always admired men who pull off this presence. The older guys, successful but understated, who show you that their style isn’t in the flash—it’s in the package. They might be wearing a sweatshirt like every guy in the room, but something about how they wear it makes all the difference.
Italian menswear enthusiasts love to speak of sprezzatura—putting in a lot of effort to seem like you’ve put in no effort at all, yet somehow looking perfect.
But there’s another version of that: what if you really didn’t spend time putting it together, but it still works? The time spent is not in the morning getting ready, but over the decades of practicing the basics and learning the details. That’s the casual cool we’re talking about here.
When the fabric is good, the cut is right, and the fit is perfect, you don’t need to overthink it.
We're excited to team up with Gustin on this piece, because like Primer, they believe that classic, enduring style doesn't have to break the bank.
Navy sweatshirt: Gustin Vintage Heavyweight Sweatshirt
White t-shirt: Gustin Vintage Heavyweight T-Shirt 2 Pack
Sunglasses: USA-Made Randolph Engineering Aviator
5 pocket stretch pants: USA-Made Gustin Stretch Twill Straight Fit
Horween leather belt: USA-Made Gustin Horween Classic Belt
Footwear: Red Wing, Clarks, Converse 70s, Birkenstock
Navy with gray is one of the core color combinations—just review about 50% of every football team in America, from the pros to elementary flag. There is an innate solidity to it that, even when paired with a plain sweatshirt and twill pants on a fall weekend, reads as strong and uncomplicated.
Heavyweight Sweatshirt
And that’s what great style does. A well-made sweatshirt or sturdy boots are more than the utility of just staying warm; they’re about staying grounded. It’s a reflection of where you’ve been, where you’re going.
Gustin's deep navy sweatshirt is a homage to heritage, drawing on the spirit of rugged knits from an era when basics were built like tanks. Sewn from extra burly cotton fleece, it carries a comforting weight but also doesn't force you to run hot.
A simple silhouette, for sure, but details like flat-locked seams, ribbed side panels with wider hems and leather patches ensure this enduring style is actually durable.
Let Your Footwear Define the Look
With such a flexible and socially adaptable core outfit, the footwear chosen can surprisingly alter the total feel. Here, four styles that have been present in every decade since the 60s, each providing a different utility and saying something different.
Thick Iron Rangers made to be tough on. Lightweight canvas Converse high-tops add comfort unbound from any trend era. Suede desert boots lean into that classic put-together casual cool, while the Birkenstocks in the exact same colors and materials instill a bohemian nonchalance that can balance the strong foundation of the blue and gray.
These gray twill stretch pants are the kind of piece that is such a simple upgrade, it almost feels like a cheat code. A 1:1 painless swap for blue jeans or khakis and a modern take on the familiar, they move beyond the usual with a refined practicality. The stretch woven into the twill fabric accommodates action, keeping their structure without feeling rigid—perfect for those days that take you from the driver’s seat to wherever the road leads.
What makes gray the ideal choice here is its ability to remain neutral without fading into the background. Gray offers a soft contrast, balancing the richer tones of the navy sweatshirt or the deep leather of the boots. Gustin mills and sews these right in the USA and sells them ready-to-ship for under a hundred bucks, what's more timeless than that?
Sunglasses That Have Always Been Here
Made famous by military pilots, astronauts, and Hollywood action heroes up to the present, the square frame aviator is like the perfect white pocket t-shirt: Completely unflashy and a statement. Randolph Engineering has been making these shades in Massachusetts since 1973, the upgrade from a disposable pair is more than domestic production, the construction and superior lenses are clear the second you put them on.
A Budget-Friendly Watch That Looks like a Million Bucks
There’s a certain elegance in that simplicity, in knowing that classic pieces—like a pair of leather boots or an understated watch—aren’t just for now, but for always. They connect you to the past, to the men who wore them before you, while reminding you that your personal style, like anything worth keeping, only gets better with time. And in a world that’s constantly changing, there’s something to be said for the things that stay the same.
The Orient dive watch is a tool built with purpose, bridging function and form in a way that feels seamless with the rest of the outfit. Much like the Red Wing boots or the twill pants, the watch doesn’t need to shout to make its presence known. Its ruggedness, with 200-meter water resistance and a tough, stainless steel bracelet, speaks to a kind of reliability that transcends decades and trends.
A callback to classic dive watches, the Mako II stays firmly in that lineage while remaining understated—an easy companion for both the city streets and weekend escapes. I've had, and featured mine, for years.
In the end, it’s not how much time you spend in front of the mirror. It’s understanding that true style isn’t about the effort—it’s about knowing what works. Like that navy sweatshirt and those gray pants, some things just fit, effortlessly.
Navy sweatshirt: Gustin Vintage Heavyweight Sweatshirt
White t-shirt: Gustin Vintage Heavyweight T-Shirt 2 Pack
Sunglasses: USA-Made Randolph Engineering Aviator
5 pocket stretch pants: USA-Made Gustin Stretch Twill Straight Fit
Horween leather belt: USA-Made Gustin Horween Classic Belt
Footwear: Red Wing, Clarks, Converse 70s, Birkenstock
What is your go-to classic style? Let's chat in the comments below!
