The Two-Season Wardrobe: How to Wear It

menswear wardrobe essentials

After my recent post on my two-season wardrobe essentials, I thought I would write a follow-up with how I typically wear these pieces. None of this is particularly groundbreaking as all of these items are very common and versatile, but I suppose that’s why I consider them my essentials. Like I mentioned then, the idea here is that I have a warm- and cool-weather version of each piece, which gives me enough versatility to wear this “uniform” throughout the year.

The first look is the more polished-leaning combination – blazer, chinos, dress shirt, and calfskin bluchers. Although many in the menswear world would call this a “casual” look, I find that in the context of real life it’s rather dressed up. I wear this when I want to look put-together but not stand out too much.

For my everyday casual getup, you can almost always find me dressed in something like the image below. Field jacket, denim, casual shirt, chukkas, and sweater (if it’s cool enough to justify it) have become my casual go-tos and get a ton of wear all year. These are the pieces I reach for when I don’t need to look any particular way but still want to be presentable.

menswear essentials casual

In both of these cases, I’d say that the outerwear is the “star” piece and the shoes provide the visual foundation; those to me are the most important pieces (and the ones I spend the most on), and everything else plays more of a supporting role.

All of these pieces can be mixed and matched more than I show here, but this is the most common iteration of how I wear them. It’s been fun hunting down these pieces over the past few years and turning them in to my closet staples. I’m sure I will continue to find more items that earn their way into my group of essentials, but for now this is what I look like most of the time. What are your go-to pieces?