Much can be said about buying your clothes in the “off-season”. That means buying wintery things in the summer and vice versa. Usually, you can get pretty good deals since companies are trying to get rid of lingering products from past seasons to make room for new ones.
Another great reason for off season buying is for getting things that are a little outside your comfort zone. Dressing should be fun. Why shouldn’t it be? It’s something literally everyone does every day. Wouldn’t we be better off to derive pleasure and find fun in the things we need to do daily? Part of that fun is trying new things. I’m sure we all have things we have always wanted to try but were afraid we couldn’t “pull off”. Well, the off season is the time to do it. Scooping up something for winter in July means you have 4 months to live with it, try it on around the house, get used to seeing yourself in the mirror in it. This familiarity makes it feel more second nature. Easier. Eventually, it doesn’t feel like much of a stretch since it’s been yours for a few months by the time it’s seasonally appropriate to wear it out of the house. You’ve had practice wearing it, so it feels more like “Oh, this old thing” than taking a risky plunge.
Of course, you could just say “screw it” and just buy the thing and wear it whenever. But I’ve always been more of an “ease into things” kind of person. When my sister and I were kids and swimming at our grandfather’s cabin up north, she would plunge right into the frigid lake to get it over with. Not me. I would go inch by inch.
I’ll give you two examples of off-season purchases that were a little bit out of my comfort zone:
Boater Hat – Have you ever seen pictures of NYC in like 1910? It’s a sea of boaters! Everyone looks dapper as hell. The problem is that a boater is one of those pieces that looks particularly costumey. That’s not a huge problem but it requires a higher level of insouciance to wear it comfortably, hence the benefit of buying it in the cooler months with an eye towards wearing it once the summer hits. My wife bought me a boater in early spring when it was still chilly. It would have looked out of place for me to wear it at that point obviously, so I waited until July 4th weekend when we all took a week-long beach town trip. It was the perfect environment and I already had a little practice since I had been wearing it around the house a little in the weeks leading up to the trip. During the day I wore it with a madras button-down shirt, chinos, and boat shoes. On the way to dinner I wore it with a seersucker jacket, blue OCBD, tan wool trousers, and burgundy penny loafers. I knew it was a bit costumey, but it was fun and it made people smile. It was a good reminder to not take myself too seriously.
Black Leather Jacket – This was something I had always wanted. I already owned a brown leather bomber jacket (a G-1 to be specific) but the classic black double rider motorcycle jacket was something that always seemed a bit out of reach for me due to its rather aggressive styling. After all, I don’t own a motorcycle and have no plans to buy one. How could I authentically wear a motorcycle jacket when I drive a Toyota RAV4? Then my wife bought one for me (a Schott, the real deal) and all those silly notions melted away due simply to how awesome it felt to wear it. The leather is thick and heavy and makes my closet smell like a baseball glove. I’m constantly pulling it on for a few minutes at a time throughout the day just to walk by the mirror. I no longer thing “Oh, I can’t possibly pull that off”, because I am now used to seeing myself in it. I can’t wait until it’s cool enough to wear it outside. And when I do, it will feel like old hat. And why should it feel inauthentic just because I don’t ride a motorcycle? Plenty of menswear is derived from pursuits we don’t generally follow. I feel just fine wearing my bomber jacket but I’m not actually a pilot. I wear tweed sport coats but I don’t go shooting at my country estate. I wear a barn coat in the winter and I don’t have a barn. These are self-imposed limitations borne from timidity. I always fear someone in the crowd will point and let out a Nelson-esque “HAW-haw!” if I wear something I consider somewhat eye-catching. But you know what? That never happens. Maybe it would have if I was 12 years old, but not as an adult. I’ve come to realize that no one really cares what you look like. As my dad’s mother used to tell him when he was a child, “Don’t worry, no one is looking at you anyway”.
And think about how these types of choices affect our kids. Wouldn’t you rather be remembered as the dad in the leather jacket than the dad in the old hoodie? The bold dad rather than the timid dad? I sure would.
Who am I kidding? At a certain age our kids think everything we do is lame, so it’s probably all for naught anyway. At least the pictures of me will look cool.