Take Your Jacket Off
The title of this article might seem a little confusing at first.
Why would someone who is into classic menswear advise you to remove your jacket?
As you know, the advice I give on this site is gleaned from all my years of trial and error. I feel it’s beneficial to talk about all the weird little ins and outs of that journey so that you never feel like you’re alone in how you’re feeling or what you’re experiencing.
And this is one thing I struggled with for a long time but I’ve never heard anyone else talk about.
Now, maybe it’s because my menswear education started with black tie, but early in my classic menswear journey, I felt VERY uncomfortable taking off my jacket if I was wearing a suit or sport coat. I’m talking about instances where the office or subway was a little too warm, or maybe I had been walking outside for a bit, or the event I was attending had sub-optimal air conditioning.
Normal, everyday things like that.
It might sound somewhat trivial, but my hesitance to ever remove my jacket in public was indicative of a deep insecurity that kept me from truly being “at ease” in my clothing, and by extension, actually looking stylish.
When I first got into classic menswear, I made sure to follow all the “rules”. One of those rules was that you don’t remove your jacket in public. After all, a proper gentleman stays dressed throughout the day! You wouldn’t remove your necktie or your shoes in the middle of the day, would you?
Usually, this rigid adherence to this particular rule didn’t cause much of a problem. I could wear my suits, sport coats, and blazers whenever I wanted and even though I was known as the “suit guy”, everything was fine.
But then there were the hot days. And then there were the really hot days. At the time, I worked in an office where most of my colleagues were from warm-weather places like Africa, South America, and India. They insisted on keeping the in-office temperature at 82 degrees! That is not an exaggeration.
That was NOT a climate conducive for wearing a jacket.
But I did anyway.
I suffered and sweated. But I didn’t feel comfortable removing my jacket. I thought it was improper. But more than that, I felt like I wouldn’t look good! I had spent all this time getting gussied up in a tailored jacket and I didn’t want it to go to waste! I wanted everyone to SEE that I was wearing a nice jacket. I wanted everyone to see how expertly I combined my shirt, tie, jacket, and pocket square! I wanted everyone to know I wasn’t one of the “regular” office guys in just a dress shirt and slacks.
Wearing tailored clothing was still novel at the time so it didn’t feel totally “me” yet. It was as if I was still playing my fancy new toy.
On top of that, I didn’t make sure that every layer worked on its own. For example, if I was wearing suspenders, I felt weird having people see them (because suspenders are somewhat eye-catching and I didn’t like drawing attention to myself), which made me feel even more self-conscious about removing my jacket.
What was going on? Where did this insecurity come from? Isn’t dressing in classic menswear (and just caring about our appearance, in general) supposed to increase our confidence level?
What I realized was that I felt like my clothes were the best thing about me, which is kind of sad to think about now.
When I got into classic menswear, I was primarily exercising my knowledge of this new hobby in two specific areas. One was out to dinner on dates with my wife, which was amazingly enjoyable. The other was at work. Unfortunately, around this time, I was in a rather toxic work environment which sapped much of my confidence. My clothes were a glimmer of joy in my otherwise unpleasant and stress-filled work days. I also viewed my clothes as something I was good at, which was in stark contrast to how I felt at work. Regardless of how bad my work day was, I knew I was “good at” what I was wearing.
The more toxic my job became, the more I leaned into the “rules”, without even realizing it. I obsessed over things like my tie and pocket square pairings, trouser break, shirt cuff length, and sock color. I felt like I couldn’t “mess up” anything when it came to menswear because that was the thing I was supposed to have the most confidence in and aptitude for.
Basically, if I didn’t look put-together then what the hell did I have going for me?
And so… I kept my jacket on.
I felt like I couldn’t risk looking anything but 100% on-point with my clothes. That meant I certainly couldn’t take off my jacket in a hot office and roll up my sleeves!
It’s only with the benefit of hindsight that I am able to recognize where that insecurity came from. I definitely didn’t realize it while it was happening.
So, what changed? Well, a few things. First, I left that toxic job, which was probably the most important thing. Second, I stopped buying a ton of crap I didn’t need. Third, I just had more years of experience under my belt.
Now, I look at my comfort in removing my jacket whenever needed to be a sign that I have overcome that awkward and unpleasant phase in my menswear journey. I view it as sign of growth, both personally and professionally. It’s an indication to me that I am in a much better head-space than I was eight or ten years ago.
I don’t think I am alone in this, though. I think that when lots of men start out in classic menswear there are things that feel uncomfortable and they can’t quite explain why. Anxiety and stress can manifest itself in lots of different ways, including how we feel in our clothes. Perhaps the source of that stress is something that is completely unrelated to our wardrobe choices.
Those feelings are normal but very few men have the introspection to really dissect why those feelings exist. And it’s different for everyone.
Hopefully, knowing you’re not alone will help you feel happier and more confident in your clothes.
So, go ahead and take off your jacket and show the world, and yourself, the great man you are.
