Over the past few years I've made something of an effort to improve my dress sense. I've still got a long way to go, but I'm improving. I've cultivated a few basic rules or guidelines that have helped me, in terms of dressing better on a more consistent basis, and spending less time and money on clothes.
Some of these rules/guidelines are below. They seem so basic, but there was a time when they weren't for me! And I still have to remind myself of these rules on a regular basis.
Fit and colour
It has taken me a long time to accept that I can love a shirt, but I can hate it on me. Where I once used to buy clothes because I liked the fabric or style, I've learnt to focus on fit and colour.
It's important that clothes fit, and complement your body shape. Make sure shoulders are just right. Make sure your shirt doesn't billow. Make sure sleeves and pants are the right length. Make sure it covers your torso properly. In short, wear clothes that flatter you.
This can be surprisingly difficult. I mention the torso above because that's a peculiar one for me. I've learned that most of my height comes from a long torso and many tops are simply too short for me.
Because of this, if I find an item that fits really well, I tend to buy multiple items. If I come across a brand or style that fits particularly well, I make a note of the details on my phone so I can make a beeline for it in the store, or order it online, when I need to replace an item.
Apart from basic modifications, I haven't used the services of a tailor much, although many publications insist that this is key. Perhaps this is the next step.
I've come to accept that certain colours work well with my pasty white complexion, and some colours do not. Blue does.
I now orient my wardrobe around the colour blue, with variations that are known to complement blue. For example, I might wear a blue pair of jeans, and a shirt that is a different shade of blue, with a pair of shoes that is blue or black or yellow.
Not only does this mean that the clothes I wear match more consistently with less hassle, it also means that I've been able to limit the items in my wardrobe. When everything matches the same broad colour palette, less variation is required in the wardrobe.
As an example, I no longer need a dozen ties of different colours to match my varying work shirts. I can stick with the same narrow range of dark blue ties.
I'm steering towards something resembling a "personal uniform"
A number of well-known people had or have "personal uniforms". Steve Jobs, with his black turtlenecks, Levi's 501s, and New Balance shoes. Mark Zuckerberg, with his grey shirts and hoodies. Tom Wolfe (author of Bonfire of the Vanities and The Right Stuff), with his white suit. I understand that Andy Warhol, Stanley Kubrick, and Alfred Hitchcock each had a personal uniform of sorts.
I don't have a "uniform" in the strict sense of the word. However, if you meet me in the same context several times, you'll notice some distinct similarities in terms of what I wear, and in some cases I'll be wearing what appear to be the exact same clothes.
I'm certainly heading in the direction of having a "personal uniform". I won't go as far as having a single outfit that I wear at all times. For one thing, I have a wardrobe full of clothes already and it's wasteful to simply throw everything out. Also, the vagaries of weather and situations in which I find myself mean that wearing a suit or turtleneck with jeans aren't always appropriate. Also, fashions change, and so do my tastes.
The key thing I do is that when I find an item of clothing I like, I buy multiple versions of the same item. For example, I have three pairs of jeans that are identical, and another three that are the same brand and design, made from different types of denim. I have fifteen t-shirts that are identical, nine of which are in the same blue and the others are in different shades of blue and grey. (If that sounds excessive, they were only $8 each and I'm scared of the day that I can't get them anymore!) I have several sets of shoes that are the same, or variations of the same design.
One caveat I'd make is that I've been burned by buying clothes that I expected to be identical but weren't. For example, the same design might differ if you buy it in one country compared to another country, and it might change over time. My general strategy is that I often buy one or two items to begin with, and if I really like it, buy multiple items very soon after when I can be confident that the item will still be available (ie, not discontinued) and sizing won't have changed.
I've loved the transition so far. It means I spend less time shopping for clothes. It means I'm always going to pick out something that I like. And it means there are consistencies with what complements what I'm wearing. (In the past, for example, I've had pairs of shoes that would work with one pair of jeans but not others. Now, the number of combinations I need to consider is vastly reduced and simplified.)
This might not be palatable for all people, or at least to the extent I'm veering. My wife made the point that she doesn't buy multiple versions of the same item because she doesn't want people to think she's always wearing the same thing. I can understand this. It's probably a more sensitive issue for women than men (could a woman anchor of a morning TV show get away with wearing the same outfit every day for a year? Of course not.)
However, I'd suggest that people notice that much. And I'd generally prioritise looking presentable and having an easier life over the possible perception that people might have of you. And if it really matters, all you need to do is let it be known to the people you see regularly (and care about) or your strategy of buying multiple versions of the same clothes.
I'm not a fashion horse and photos from 2015 will still make me cringe!
These are some of my high level strategies when buying clothes. Am I fashion horse? Not by a long shot. Does my entire wardrobe align with this philosophy? Not by a long shot. Not yet. Will I look back at photos from 2015 and cringe at what I was wearing? Probably!