“I’d love to dress better but I just can’t afford to.”
Every Christmas season I hear this familiar lament from young male relatives. And I counter it with an argument I’ll put into writing, in case you or someone you know is telling themselves this convenient lie. For the truth is if you can afford to dress yourself, you can afford to do it well. What it takes is not necessarily an excess of money but of time and effort. And that is what they really “can’t afford.”
I’ll start by saying, as I have before, that dressing well is not about how expensive your wardrobe is. It is about knowing yourself, developing a personal sense of style, and investing in quality and a good fit. Those criteria take time to mature, they are skills that must be built through a lot of trial and error. And so I often question my relatives on whether they actually want to dress better. Because if they did, they would find a way. And buying stuff is not at the heart of the matter. As the great G. Bruce Boyer says about shopping in his most recent book True Style: “Most people think they’re buying style when in fact they are only buying clothes.”
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I wrote a series of style resolutions that I believe will make you a better person. Now’s about the right time to read that list again, I’d suggest. It contains my advice for how to develop and build your approach to dress, which includes following the guidance of others, dressing with intent (instead of just throwing on whatever is around) and caring for your wardrobe. I will admit that this is a long process – I started over a decade ago and have a lengthy road ahead. In fact, I will never arrive at my destination; it is the journey that matters.
Clichés aside, I won’t ignore the fact that money must be spent. But if spent wisely, on high quality items, your wardrobe will actually be an investment. I don’t mean that you’ll be able to resell it in years to come, but it will last longer and look better than poor quality clothes. And if spending is a concern for you then I have a simple solution: buy less but buy better. It goes against the disposable, cheap culture we’ve been raised in, but instead of buying four or five pairs of cheap shoes over the next few years, buy one pair of excellent shoes. And apply that approach to the rest of your wardrobe. Strive for the very best, just get less if cost is an issue.
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I am at least heartened by one thing: that so many men want to dress better. I hope this wish stems from a real aspiration to lead a more elegant life because if it does, it expresses a deeper desire to live life to one’s full potential. And that desire is really why dressing well matters.
Pedro
You hit it on the head when you say it takes time as well as trial and error. My son and his cousins like to call me ” dapper Dan” for the way I dress. Like you they say say how much they wish they could as well. Reality is they are lazy, they just want to put something on quickly. Money is better spent on video games ( there all nearly 30)
I spent a few years away from Bay Street, and now that I am back I will say the “young guys” (let’s say 25-35) seem better dressed now than they did 2005-10.
Slimmer trousers, cleaner cuffs, more MTM shirts – these are all good things. In 2005 I remember many guys looking like their suits are 1 or 2 sizes too big…this look is more rare now. I don’t recall ever seeing a pocket square in 2005, but now I do. Baby steps.
Something that would be very helpful is a guide for simple, classic, basic pieces and where to get them in Toronto for a fair price. Spier and Mackay is one Toronto brand that comes to mind which makes high quality, not terribly expensive pieces that are classic as opposed to trendy – I already have some trou ($120), shirts ($50-80) from them, and plan on a blazer ($400ish).
When I hear this objection, I try and steer people away from thinking “brand.” If you know something about the ways clothing and shoes are constructed, and can apply that knowledge, you can get some wonderful deals. And remember to at least buy your tailor a coffee from time to time…
It’s hard for many of us who have never been taught what correct fit looks, and feels, like. I think that’s a base knowledge that has been lost, so many think that throwing money at expensive brands will make up for it – that this will automatically ensure a great cut and fit. Not true.
8 Comments
Simon
January 4, 2017 at 9:04 am
Pedro Mendes
January 4, 2017 at 9:18 am
Shane Crawford
January 5, 2017 at 8:50 am
416expat
January 5, 2017 at 10:48 am
Pedro Mendes
January 5, 2017 at 11:57 am
Chris Cox
January 7, 2017 at 10:51 am
Pedro Mendes
January 8, 2017 at 10:45 am
Torontoredhead
February 28, 2017 at 11:41 pm
When you asked your relatives if they wanted to dress better what was their answer?
Faced with the reality of the situation, they all admitted they had bigger priorities in their lives – which was a little heartbreaking.
Pedro
You hit it on the head when you say it takes time as well as trial and error. My son and his cousins like to call me ” dapper Dan” for the way I dress. Like you they say say how much they wish they could as well. Reality is they are lazy, they just want to put something on quickly. Money is better spent on video games ( there all nearly 30)
I spent a few years away from Bay Street, and now that I am back I will say the “young guys” (let’s say 25-35) seem better dressed now than they did 2005-10.
Slimmer trousers, cleaner cuffs, more MTM shirts – these are all good things. In 2005 I remember many guys looking like their suits are 1 or 2 sizes too big…this look is more rare now. I don’t recall ever seeing a pocket square in 2005, but now I do. Baby steps.
Something that would be very helpful is a guide for simple, classic, basic pieces and where to get them in Toronto for a fair price. Spier and Mackay is one Toronto brand that comes to mind which makes high quality, not terribly expensive pieces that are classic as opposed to trendy – I already have some trou ($120), shirts ($50-80) from them, and plan on a blazer ($400ish).
Thanks for the comment, Brad, and I’m glad to hear things are looking up sartorially in your neck of the woods!
When I hear this objection, I try and steer people away from thinking “brand.” If you know something about the ways clothing and shoes are constructed, and can apply that knowledge, you can get some wonderful deals. And remember to at least buy your tailor a coffee from time to time…
Great advice, Chris, thank you.
It’s hard for many of us who have never been taught what correct fit looks, and feels, like. I think that’s a base knowledge that has been lost, so many think that throwing money at expensive brands will make up for it – that this will automatically ensure a great cut and fit. Not true.