This article exists as part of the online archive for HuffPost Canada, which closed in 2021.

How To Find Your Own Personal Style

Because fashion can be expensive, exclusionary and frankly, sometimes, kind of confusing.
If you love cashmere sweaters, think about why. Do you value comfort? Practicality?
Thomas Barwick via Getty Images
If you love cashmere sweaters, think about why. Do you value comfort? Practicality?

Fashion should be fun and accessible, a way to marry beauty with function, and a means of self-expression.

But let’s face it: fashion can also be expensive, exclusionary and frankly, sometimes, kind of confusing. (Why, oh why are tops with shoulder cutouts a thing, and why haven’t they gone away yet?)

If you’ve never thought much about your own style before, but it’s something you want to develop now, you’re certainly not alone. Many of the people who hire stylists are in a transitional phase of some kind, Vancouver stylist Michelle Addison told HuffPost Canada. Often they’re starting a new job, or returning to work after having kids, or moving through some other kind of change.

If you don’t know much about fashion, it can seem intimidating. But once you know where to start, it can actually be a lot of fun. Here’s how to develop your own true-to-you personal style.

Think about the clothes you love

Often, people think that developing a sense of style means buying a lot of new pieces. But “the place where I’d say to start is in your own closet,” Toronto-based stylist Rebecca Jacobs told HuffPost Canada. “It’s so full of data about what works for you and what doesn’t work for you.”

Go through your clothes and identify the pieces you really love. What makes them special? Are you attracted to form-fitting neutral-coloured shirts because they’re comfortable and go with everything? Is your favourite piece a dress with a bright pattern, or a pair of pants you can dress up or down?

Figuring out why you keep wearing certain pieces can unlock a lot of information about what’s important to you.

Think about the clothes you hate

Is your closet full of clothes you impulse-bought but never wear? First of all, you’re not alone. Second of all, get rid of it — it’s nonsense to keep something around that you’re never going to wear.

Thirdly, start thinking about why you hate it. Is it too small? Was it trendy when you bought it but now feels dated? Is the fabric itchy? Did you buy it because it was on sale even though you don’t really like the colour? Maybe someone told you they liked it, so you thought that must mean it was nice, even though you actually hate it.

Figuring out what you want to stay away from will tell you a lot about yourself, and about what not to buy again.

Watch: What to do with the old clothes you don’t want anymore. Story continues after video.

Seek out inspiration

Is there a celebrity whose fashion choices you admire? A painter whose aesthetic you’d love to step inside? A movie you wish you could live in?

Keeping track of your visual influences can inspire you, and make it easier to identify what your own personal style actually looks like. Both Jacobs and Addison say they encourage their clients to use Pinterest to look at things they think are beautiful or structurally interesting. “That can be clothing, it can be architecture, whatever helps you find what you like,” Addison said.

Instagram can provide great visual inspiration to a wide variety of different tastes, as can fashion or photography magazines. Keep seeking out images until you find something you really love, something that moves you. “We can get influences from pretty much everywhere now,” Addison said.

Dress for the body you have

Jacobs and Addison say it’s common for people to approach them for help, only to hear that their clients want to put their fashion development on hold until after they lose weight. Both stylists say not to do this.

Weight loss is a personal choice, but Jacobs encourages people to remember that “our body isn’t necessarily something that can be easily [changed].” For many people, healthy and long-lasting weight loss takes a lot of time.

Addison says delaying re-thinking your wardrobe because you want to lose weight is unnecessary. “Time is so limited, why wouldn’t you want to look your best any time?” she said.

Also, remember that figuring out your style isn’t a commitment to spending a ton of money on clothing in that size.“It’s very rare that someone’s ready to spend tens of thousands of dollars and upgrade their wardrobe right at the top,” Addison said. “It’s a slow process of building your basics, and it’s seasonal.”

Don’t be discouraged by the young, thin whiteness you see everywhere

Although Pinterest can be a really helpful resource, Jacobs said she and her clients are often frustrated by how similar the models look.

“The vast majority of people you find on it, they look the same: they’re usually white, and they’re usually very thin, very young people,” she said. “My clients mostly don’t look like that.”

It’s by no means limited to the platform itself. A lot of fashion coverage is overwhelmingly focused on thin, white women, which makes people who don’t fit into that narrow standard of beauty — created and upheld by the media — feel excluded. Jacobs said this focus, which completely omits many types of beauty, discourage people from trying something new, because they feel that it won’t work on them.

It’s still a frustratingly homogenous scene, but there are an increasing number of online spaces devoted to fashionable people of all shapes, sizes, and colours.

Don’t spend time thinking about so-called “problem areas”

Dressing to hide a body part you don’t like is no way to live, Jacobs said — and often, thinking too much about what you don’t like about your body is counter-productive.

“We have this tendency, in the areas that we feel most insecure about, to cover them with more fabric,” she said. Very often, this is the stomach, she said — but something that’s really loose or bulky around the stomach “just adds more visual weight to it,” she explained. “It’s usually more flattering to do the opposite.”

In fact, tucking shirts into pants or skirts is something she generally recommends: “it creates a waist, and gives us a shape, and often allows us to wear pieces we already have in a way that is more flattering.”

Have fun with your work style

Addison said she often encounters people, particularly women, who feel like they can’t be true to their style when they’re at work. She wants us to abandon this idea. “It’s kind of an old-school, sexist mentality that we can’t dress feminine or dress fashionable and be taken seriously,” she said.

Of course it’s important to be professional at work, and some positions require employees dress up more, or wear uniforms, or wear certain pieces for safety, but as long as you’re wearing something work-appropriate, and something you can actually do your job in, “I encourage people to be expressive and fashionable,” she said.

Maybe this means a knee-length skirt and a blouse, but the blouse can be in a fun colour, or the skirt has a bold pattern. Maybe the outfit itself is fairly neutral, but the shoes and the accessories are more daring.

For men who have to wear a suit, she suggests having fun with footwear. Ties and pocket squares can be fun, Addison said. Even a haircut can change up an otherwise boring outfit. “There are definitely ways that you can express yourself within the guidelines of appropriate workwear,” she said.

Invest in the pieces you’ll wear over and over again

Often, we’re tempted to splurge on big items, like a dress you’ll wear to a friend’s wedding. And there’s nothing wrong with doing that, but think about where you really want to be spending your money — is it on an outfit you’ll wear twice, maximum, or on something you’ll use every day?

Addison suggests thinking about clothing in terms of cost per wear, in which an item’s value is correlated to how many times you use it. For example, if you buy a dress for $200 and you wear it once, it cost you $200 to wear it that one time. If you wear it twice, it cost you $100 each wear.

It makes a lot more sense to invest in the items you’ll wear a lot. Coats are a good investment, particularly for those of us who live in areas that get cold much of the year. Shoes or boots can be a good investment, too, since we wear them a lot — for many men, a signature pair of sneakers can do the trick.

Give yourself permission to enjoy fashion

Addison and Jacobs say that one of the benefits of working with a stylist is that they’ll encourage you to try things you like but would never try on by yourself.

“People have a certain idea in their head about who they are,” Addison said. Her clients will often tell her they’re not stylish or creative, but in reality, most people know what appeals to them, even if they don’t feel like it’s something they can “pull off.”

“There really is this paralyzing fear of wearing the wrong colour,” Jacobs said. “And people are concerned about wearing the wrong shape, or being too formal.” Most of the time, people end up surprised that they look and feel good in outfits they thought they could never wear

“I hear it all the time: ’I never thought that could work for me, but I needed permission to try it,’” Addison said.

20 Ideas For 2020 is our series that explores easy ways to take action on the ideas and changes you may have already been thinking about.

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