The Styles Ages of a Man
There's a certain dignity to dressing your age. I think a great marker for a stylish man is knowing when it’s time to switch up his look, when it’s time to retire a specific garment or just simply understanding when a trend is not meant for him and where he is in life. I can’t tell you how often I see grown men out in these streets who look like they’ve raided the 17 year-old son’s closet.
Fellas it’s important to evolve in your look, not everything ages well. Here’s a great example, a 45-year-old overweight bald man wearing a short sleeve polo shirt with a popped collar, destressed skinny jeans, and a belt with buckle the size of a billboard will be seen as a joke. The same can also be said for a 19 year-old college student attending lectures in a $3000 bespoke 3-piece suit.
Either way both ages of men are not dressing their age. Now, to be clear I’m not saying that once you hit certain ages that you must completely start from scratch. I’ve always spoken about the importance to invest in pieces that can be interchanged and be useful as you age. Knowing when to experiment and when to fall back on timeless and reliable options is very important as a man grows.
So today, let’s discuss what a proper style evolution should look like for a man with style. Going through what the 20’s, 30’s and 40’s should look like. I’m not going to address the 50’s because if you follow this trajectory any age after your 40’s should be a so easy and effortless.
Men In Their 20’s
You can get away with pretty much any look, this is the time to play with colours cuts, fabrics, genres, and shapes. Enjoy this time. But if perception matters to you, now is the best time to start building a wardrobe that works for you, rather than against you. Use this time in your life to assess your style objectives, and how you want to be perceived with your clothing.
In my 20’s I was convinced that I would be working in corporate space and desired a more professional wardrobe. Suits, sweaters, and button ups that I would transition well from the office to dinner with friends. I hated it. I was building a wardrobe I thought I was supposed to be building for someone in college studying a potential corporate profession. I forgot to establish a realistic balance. Your 20’s are a discovery phase of the style journey. This period should include risk playing with trends and figuring out what works for you.
Men In Their 30’s
Speaking as a man in his 30’s, I can confidently say this is the fun age! At this phase, your style should be evolving towards pieces that will look great year-round and not what’s hot right now. I’d like to think that at this point in your life you’ve settled into an aesthetic you like, and are exploring trends that elevate or compliment the aesthetic you’re comfortable in.
At this point, most men’s wardrobe objectives would be to present a more Established Man. By that I mean a look that displays your confidence, mixes your youth and maturity with wardrobe staples that will present the most authentic version of yourself. This is also the decade where you should invest in having a good suit in your wardrobe if you don’t already have one. The key to successful style in your 30’s is understanding your body shape and figuring out what cuts best compliment you since most men aren’t trying out every trend. Going the extra mile is what will separate you from your contemporaries. Introduce new patterns and fabrics and try them out with the closet you’ve already built.
Men In Their 40’s
At this point in life your style should really be effortless, and although it doesn't happen overnight your 40’s will be a transitional point. Most men have gone through different career paths and have figured out what works and doesn’t work for this new chapter in life.
Dressing at this age should be like driving on autopilot. There are fewer mistakes to be made and there’s no need to test out every trend emerging in fashion. You know what works for you, and what compliments you best. Unless you’re in the middle of a mid-life crisis and suddenly think your Jean-Michel Basquiat.
Now I’m not saying break out the orthotics, the oversized sweatsuit, and a walker yet. There are still some amazing style moments to be made. Think of it this way, if your 30’s were about presenting the Established Man, then your 40’s should be about introducing people to the Polished man.
Style in your 40’s mean doing away with the aggressive younger men's styles that say, “look at me!” Trying to wear the clothes you wore fifty pounds and a different hair color ago is unlikely to flatter you. Rather your 40’s reflect the refined elegance of a man that knows what he likes and feels confident about his place in the world. Your aesthetic should say “I know you're looking at me.”
And there you have it! I really hope this article has inspired some reflection and where you currently are in your style objectives. I would love to hear your thoughts on this one, what age bracket do you currently fall under? Has your styled evolved as you’ve matured? As always let’s keep the conversation going in the comments, until next time.