Dressing your Age. 🎯

Greetings Gents

It’s me again, with yet another SG style note in your inbox. Our last week’s session about Style Pandering was a rather contentious one and what seemed to be a mixed bag. Nonetheless, I hope it was an insightful read and here is the result of the polls and feedback. From beginner to advanced, my goal with this newsletter, is to always help each and every one of you look your best. And on that note, it seems to be the perfect time to dive deeper into dressing your age. 

Style is quite a subjective topic, and I’ll start by stating that it’s not my job to tell you what to wear, but to simply offer some guidance. As we age, maintaining our imagery and confidence can become quite a bit challenging. You see, as men, the older we get, the more is expected of us. To be better leaders, providers, decision makers, and a source of wisdom and guidance from those around us. And so, how we present ourselves has a lot to do with whether others see us as such. ‘Dressing your age’ is not really about what to wear after all, but instead, a blueprint of ‘what not to do’.

Younger men are given more grace in society, as they are simply being afforded the opportunity to find themselves. To constantly try new things…no matter how wild. Middle aged to mature gentlemen, on the contrary, are expected to have ‘arrived’. You know... to be sure of who we are, and not still trying to cling on to our youthful years. 

This week, we had the privilege of shooting with two gentlemen from entirely different generations. Irvin, is a 63 year-old school teacher and fashion influencer, while Nivas is a 32 year-old neuroscientist and part time actor. For those who have been struggling to look the part, here are 3 simple tips of mine, to keep your style pristine regardless of what stage of life you’re in. ​

1. Sweet Feet.

You just gotta have em’. If you’re looking to make dressing well an effortless part of your routine, then foundational footwear is key and a must have. Last week, I talked about understanding your lifestyle, from work environment to preferred leisure activities. Your choice and quality of footwear is arguable the most important part of any outfit, as it will usually dictate the rest of the attire. For instance, athletic sneakers eliminate the option of wearing trousers, and lace-ups look rather underwhelming when paired with jeans. And so you have to choose wisely. Depending on lifestyle of course, my typical recommendations for most men will fall somewhere between a pair of loafers, minimal sneakers and chelsea or lace-up boots. Either of these options are versatile enough to take you from the office, to your favorite restaurant or bar, without feeling out of place. Whatever you decide, be sure to invest in a quality pair that doesn’t sacrifice comfort. A good way to think about this is… "What pair of shoes would I pack on a one week business trip, and with a single carry on luggage?"

2. Mastering your Tailoring.

This one can get rather dicey, but for the sake of simplicity we’ll keep it vanilla. Tailoring is an art, and is entirely dependent on a.) Your physique and body type, and b.) your personal preferences. Your fitness plays a large part on how well garments fit you, but we’ll save that interesting topic for another day. With that said, you can clean up your style significantly, by simply focusing on your garment length. Your pants should have no longer than a half or quarter break, to avoid them from bunching up at your ankles.

Nothing screams “I’m old and have let myself go”, louder than excess fabric hanging around the top of your feet. For casual jackets and long sleeve shirts, be sure to keep your sleeve cuff at the top of your wrists, and the body length of the garment hemmed about the middle of your pant zipper or slightly above. I personally tailor all my short sleeve shirts and t-shirts to this exact length, and you’d be surprised how much of a difference this makes, especially when untucked. For suit jackets, using your first thumb knuckle (from your wrist) as a stopping guide, often provides for a perfect jacket length. You may check out our How to Tailor video guide, for a little more information on tailoring and alterations. 

3. Diversify your portfolio. 

We are all familiar with the ‘sneakerhead’. Heck, all or some of us, used to be him at some point in our lives. But I hope you’d agree, that there’s absolutely no need to own dozens of the same items, in different variations. 🫠 So you’ve got a few dope casual jackets like a trucker or lightweight overshirt, but do you own a well-tailored blazer? Or perhaps you’ve got a solid pair of loafers or dress shoes, but do you own a pair of casual sneakers or boots?

A few Saturday evenings ago, I attended a graduation party, where I saw a dapper looking 40 something year old gent, in a tucked in button down shirt with rolled up sleeves, pressed trousers, and well shined lace ups. He thought he was killing it, and he did look nice. But there was only one problem. It looked like just got off the clock, with his finance bro attire. I share this story because, we should all aim to avoid being that guy. The one incapable of the ebb and flow. Like the Gramps in the middle of park, with a full set of trousers and a pressed dress shirt, on a hot sunny afternoon. Trading the button down for a polo shirt and the lace ups for a pair of loafers, would have made for a more casual but elegant attire, and much better suited for the occasion.

One of the biggest issues that plagues most guys, when it comes to dressing appropriately, is the inability to understand time and place. The older we get, the more we seem to forget the importance of context. Yes, there is a place for neatly pressed button down shirts and suits, but there is also a place for hats, polo or casual collared shirts, and casual sneakers too. But knowing ‘when’ to pull each out, and how to style them, can make all the difference. And without this diversity in your closet, you’d simply be out of options.

And that’s pretty much it. I try to preach to everyone around me, that ‘Less is indeed More’. It’s a mantra that I try to live by, and it’s no different when it comes to style. I hope you can see with these stylish outfits, that regardless of age, your style really doesn’t have to skip a beat. From a boomer to a millennial, it all comes down to confidence and execution. When in doubt, lean on these 3 principles to keep you honest, and focus on the things that matter most. Make time for yourself, take pride in your appearance, and then get out there and live your best life. You totally deserve it!

So what would you like to see me write about next? Feel free to drop your suggestions below, or reply back to this email with your thoughts and comments. I read every single one and it’s always great to hear from you Gents…and ladies too! Until next time.  🫡

Sincerely,

F. Lawson

Creative Director

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