As someone who has lived in Europe and travelled around the globe, stylist, fashion teacher and artist Michael “Ozzie” Osbourne has noticed that men in North America often have a harder time stepping out the box when it comes to fashion.
“It’s really hard for men, I find, to be stylish – they don’t want to seem too feminine,” he said. “It’s more difficult for them to step outside the box of jeans and t-shirts or hoodies.”
For Osbourne, a Jamaican-born Caribbean Black man, fashion is deeply tied to culture. A stylist for more than 15 years and a fashion teacher at Pacific Design Academy for the past three, helping others find joy and confidence through style is a core part of his passion.
Osbourne knows that his style is his own, and doesn’t expect people to copy him. Good style, he says, is less about copying someone else and more about developing the skills to find what feels and looks best for you and put your best foot forward.
With the new year often sparking fresh starts, Osbourne is offering Victoria News readers practical tips to help men build confidence in styling themselves and self-expression. He has also put together four looks that show how he applies these principles to his own wardrobe.
Start with the basics, do them right
The first thing to do is actually very simple: start assembling the basics. “Every man should have the ten classics,” Osbourne says. These include a plain t-shirt, dark wash jeans, chinos, button-down shirt, chelsea or leather boots, crewneck sweater, blazer, classic sneakers, dress shoes and a versatile jacket.
Quality matters. Investing in well-made basics can mean spending more upfront, but it often saves money in the long run. “You buy a classic pair of good shoes, you know, $400, and that’s going to last you sometimes 10 years. It’s just worthwhile.”
But perhaps the most important thing with building a polished-looking basic wardrobe is Osbourne’s greatest “secret”.
“I always have one big suggestion for everybody: use a tailor.”
Tailoring can be the difference between something looking elevated or cheap. “A guy can buy a $2,000 suit, and it’s really expensive. I go buy a $200 suit at Value Village, but then I get it tailored and it fits me. That’s the secret.”
In today’s era of mass production, most clothes off the rack will fit poorly on most body types. That plays into Osbourne’s other paramount piece of advice: “Everybody should know their measurements and their body type,” he said. “Then you can just got in a store, and know exactly what’s going to fit you.”
Luckily, in today’s day and age, learning how to find one’s measurements and body type can easily be done online.
Once comfortable, play with colour, shapes, layering and statement pieces
For those who have never done anything complicated with their style, Osbourne recommends starting off with creating a monochromatic look – all the same colour – from head to toe. A step up from that would be tonal, focusing on one colour but in different shades. For example, using different shades of green.
Once comfortable, you can try colour blocking, using pops of solid colours in one item of clothing, such as an accessory.
“You can go all black from head to toe, and all of a sudden your kicks are pink. Or your hat is purple.”
That little splash can make a huge difference. “Colour is really important. It can really make someone’s eyes pop.”
Once you’ve mastered the basics and colour, then you can start playing with layering and statement pieces. These can be items with interesting patterns, shapes and colours and found anywhere from thrift stores to high end boutiques.
“You just need one piece in the outfit that’s like an ‘oomph’,” he said. “You want to attract people towards you.”
Osbourne also suggests adding pieces such as wool trousers, a tailored overcoat, a straight-leg jean, a neutral hoodie, a minimal watch, scarf and everyday structured bag.
When looking for items, consider your style and lifestyle, whether that’s sporty, business-oriented, casual or artistic.
Fashion isn’t about being the funkiest person out there, he says. It’s about staying true to yourself and elevating that.
Seeing men step into that confidence is one of the joys about the work that he does, Osbourne says.
“I just love to see people change and enlighten and feel better about themselves. It’s not just about the clothes, it’s a lifestyle, you know? It’s getting the best out of you.”