Casual doesn’t mean careless. That’s the rallying cry for Day 5, an outfit that dispels the mindset that “trying” means uncomfortable. We’re all about killing the stereotype that you have to choose between feeling good in your clothes and looking good in them.
In the style world, there’s often this unspoken divide: you’re either dressed up or you’re wearing an old band t-shirt and gym sneakers. But what about that middle ground? Today’s Getup is all about, “I care about how I look, but I don’t need a suit and tie to prove it.”
This outfit is for those who believe that comfort and style aren’t mutually exclusive. It’s a nod to the guy who wants to look like he tried without feeling like he’s out of place.
Denim Trucker Jacket
The denim trucker jacket, often synonymous with the Levi’s Type III design, has achieved an iconic status in men’s casual style that few garments can rival. First crafted in 1967, the trucker jacket, with its distinctive “V” stitching and dual breast pockets, has managed to strike a balance between practicality and style, making it a perennial favorite for over five decades. While variations like the Type I and Type II jackets have their own merits and historical value, it’s the Type III that resonates with modern sensibilities. Its continued appeal isn’t just nostalgia; it’s a testament to enduring design and versatility.
Whether vintage with a capital “E” on its red Levi’s tab or a modern adaptation, this jacket allows for a comfortable, but form-fitting silhouette, serving not only as outerwear but as a layered addition to an outfit. This layering adds visual complexity and a bit of autumnal heft as temperatures begin to drop, making it a functional piece for transitional weather.
In this context, the trucker jacket’s charm lies in its understated sophistication; it’s neither flashy nor boring, avoiding the extremes that often make a garment hard to wear or too pedestrian.
Men often misunderstand the role of the hoodie in a well-curated wardrobe, falling into one of two extremes. Some use it as a symbol of rebellion or laziness, essentially saying, “I don’t care what people think; I just want to be comfortable.” Others dismiss the hoodie outright, declaring with a snooty mid-Atlantic accent that “A gentleman would never wear such a thing.” Both are pretty silly.
The hoodie can, in fact, be integrated seamlessly into intentional casual outfits. The secret lies in choosing a well-fitted hoodie—neither too baggy nor too billowy—that can function as a layering piece. Opt for a low-key, solid color and pair it with other items that make the hoodie an IYKYK statement. Far from a careless or ungentlemanly choice, the right hoodie can add both comfort and style while grounding a casual outfit in an appropriate “everyday-ness”.
“What are we just wearing long underwear as shirts now, Andrew??” This isn’t the Fruit of the Loom-style thermal you wear while shoveling snow. This one by Buck Mason has a fine knit that acts more like a long sleeve t-shirt with texture. I’ve had this cream one for a couple of years and it regularly shows up in my personal rotation as both a layer or a simple solo top on a casual day. I dig it so much I bought a second one in blue.
A pair of hefty twill olive chinos is such an easy alternative to jeans, it’s amazing more men don’t bank on them. Their chameleon-like versatility allows them to match the dress level of whatever they’re paired with, whether it’s a casual t-shirt for a weekend outing or a crisp shirt for a more professional setting. This adaptability makes them an invaluable asset in a man’s wardrobe.
Originally designed for military officers, these trousers were crafted from a heavier, coarser fabric, boasting wider legs and a higher rise—a nod to the mid-century tailoring. While contemporary interpretations have evolved to offer a range of fabrics and fits, the essence of the officer chino remains: a commitment to quality material and a structured fit.
Chunky Gray Suede Boots
I love these gray suede boots: On the surface, they channel the hardiness we expect from boots—built for endurance, they’re the footwear equivalent of a screwdriver. But suede is a more refined leather that isn’t designed to be beaten into the ground. It’s this juxtaposition of rugged and refined that makes for a smart, stylish boot.
I hope you liked Fall Getup Week this year, check out the other outfits and let me know which you liked most!