The road to being well dressed is paved with questionable fashion intentions. What makes a man well dressed in the first place? This is the question and for most men, the answer is pursued well into adulthood.
The fork in this metaphorical fashion road is choosing between being stylish and being trendy. Make no mistake, there is a distinction, and stylish ALWAYS wins. The difference is that style is something that lasts, it’s timeless and not determined by the brands you wear or the money you spend. Being trendy means constantly resetting your wardrobe, chasing the latest fad, being behind the ball and constantly underachieving your style goals. Trendy is sagging pants, style is… pants that fit. Trendy is a popped collar, style is a fitted button down. Trendy is telling people you’re chill because you wear “insert ‘chill’ brand here”, style is simply being chill. Trendy works once, style always works. Here are the things you need to know to gas your trend chasing habits and achieve a stylish wardrobe that will make you look better for longer.
First, style is timeless.
Learning how to dress takes time, experience, and it takes experimentation. It’s a game of patience because to understand what makes a well-dressed man you need to understand what it is to be stylish. And what is stylish will stand the test of time. There’s a reason that the Ray-Ban Wayfarer sunglasses looked good on JFK Jr. in the 50s and 60s, made John Belushi a cool cat in the Blues Brothers in the 80s and have been worn by every music festival goer in the last five years. Similarly, there’s a reason that a no nonsense brown oxford or derby dress shoe can not only compliment any well tailored suit but can be worn down with chinos, denim jeans or shorts. These shoes were popularized in the 1800s. What does that say about the longevity of style?
Learning that style is timeless gives you the framework to recognize clothing that will be wearable beyond one or two seasons. And once you establish this framework, picking clothing will become 10x easier. Without it, you’re left clinging to the flavour of the week, the “IT” brand, or the trend the latest and greatest pop star has adopted. Kylie Jenner aside, when was the last time you threw on your Von Dutch trucker hat before leaving the house? Exactly.
Second, style starts with the basics.
For any guy who finds dressing well difficult, fear not. Being stylish is about working with basics that suit multiple occasions. Your highlighter neon yellow tank might have been a beach favourite in 2013 but how does it stand up to a navy or white V-neck tee that you can wear from the beach to the restaurant to the bar without changing once?
Start with basic coloured T-shirts or button ups: blues, greys, whites, or pale colours that don’t jump out too much. When it comes to pants, opt for dark wash denim sans distressing (the lived-in look you would probably pay double for) or clean looking chinos. On your feet, again, keep it simple. Plain solid colour sneakers like Vans or Chuck Taylors are super versatile for a casual look. Dress an outfit up with a loafer or suede oxford. Remember: less is definitely more when it comes to being stylish. You’d be surprised at how many outfits can be put together with these basic items.
Third, style comes from attention to detail.
I don’t care if Joe Billionaire walks in the room in a $3000 suit, if it doesn’t fit properly, he’s gonna look like trash. Sorry, pal. This might be the number one piece of advice any guy can use to improve their style game: wear clothes that fit properly. This means wearing clothing that compliments your figure. Going casual? Straight leg and slim jeans should be your bread and butter since its the cut that gives a good clean silhouette and eliminates any excess fabric that looks untidy. A good fitting t-shirt is one that is snug to your arms and neither tight nor loose around the torso (you don’t want your buttons bursting under pressure but you don’t want to look like a milk bag either). Find the happy medium, and if you can’t find it, get it tailored. Tailors are your friend.
Attention to detail is more than just the fit of your clothes. Accessories can have a huge impact on your style. Do your shoes match your belt? They should. What about your watch band? If they all line up then you’ve automatically taken your style to another level–Way to go. Also, consider your hairstyle. This usually starts with a decent barber and learning what style looks best for you. As someone with unmanageable, frizzy, coarse hair, this has been the bane of my style existence for my entire life. Unless you’re gifted with great looking and manageable hair, learning how to groom and style your hair takes lots of time. If you’re in my camp, hopefully you’ve honed your hairstyling skills. If not, start now. Same goes for facial hair.
Keeping these in mind, any guy can start building a wardrobe and a look that reflects their personality and exudes confidence. Once you’ve nailed these style basics, you can start experimenting with different colours, patterns and trends. Trends are not the enemy if you don’t abuse them–they can be the sprinkles on your style sundae. Just remember that trends will never be the foundation for any stylish man, so build your stylish wardrobe starting with some versatile basics and go from there.