TOM* Fashion Week Outfit Diary

I was lucky enough this past week to be able to attend Toronto Men’s Fashion week at Waterworks downtown. Myself and some other peeps from Novella were able to tag along to the illustrious coattails of our fearless editor.

It’s not the first time I’ve been to fashion show, but it is the first time I’ve been to TOM, and I had no idea what to expect.

The idea of attending a fashion show is daunting. You obviously want to look on trend and cool, but not like you’re trying too hard to be on trend and cool. It’s a fine line to balance on, same with the question of whether you need to dress up or dress down. After actually going, I can say that there’s a real mix of what people wear. There are people dressed to the absolute nines – high heels, floor-length dress, suit and tie – and there are also people taking it down a notch – denim on denim, all black, I even saw a guy in sweatpants.

Essentially, my biggest takeaway is this: just wear whatever you want but be confident in your decision and it’ll show. The coolest (and probably most photographed) people there are the ones you see just being themselves. Not that my own advice stopped me fro having a breakdown while getting ready for the shows every night, but I still stand by it.

After all of my anxiety and second-guessing, here is what I wore to Toronto Men’s Fashion Week.

(Please excuse the colouring of my pictures – it was dark and I tried my best with an iPhone 5s.)

Day 1


Since it was Men’s fashion week, I decided to go with a menswear-inspired look for the first day. I paired a white tuxedo shirt with blue jeans and a corduroy coat. To finish the look off, I decided on a pair of brogues and a clutch, both in different shades of brown. I wasn’t sure if all of the brown tones would work well  or just end up clashing, but I was running late, so I just said “monochrome,” with a flourish and left.

Outfit Details

Coat – Na Nin Vintage

Tuxedo Shirt – Zara

Jeans – Urban Outfitters

Shoes – Urban Outfitters (These are at least five years old, here are some similar ones.)

Clutch – American Apparel (Not available anymore, here’s a similar one.)

Day 2


On day 2, I went full 80s. Well, nearly. Full 80s would’ve been if I had also been able to do something cool with my hair. Alas, it was flat and decidedly not 80s, but I did don a bright red leather jacket complete with nice, big shoulder pads. Underneath it I kept it simple with a plain white tee and high-waisted trousers. Because I knew it would get warm in the venue, I needed something else to bump up the energy in my look, and I found it in my old blue suede booties.

Outfit Details

Jacket – Black Market Vintage

Tee – Anthropolgie

Trousers – Urban Outfitters

Shoes – Topshop (They’re pretty old, so here’s a pair that are similar.)

Day 3


By day three, I had had just about enough of panicking over every outfit choice. I was trying too much to be different, to stand out from the crowd and that resulted in me trying on combinations that just really weren’t me. In the end, I decided on a pretty classic Tash silhouette of loose high-waisted trousers with a tee tucked in and a long coat overtop. I liked what I had on and I felt like myself, which I think is really all one can ask for when one attends an evening celebrating fashion and style.

(In hindsight, this really wasn’t the best outfit to pick for creds.)

Outfit Details

Coat – American Apparel (Not available anymore, but I found one kinda similar.)

Shirt – Anthropologie (Sold out,  here’s a similar.)

Trousers – Oak + Fort (Sold out [AGAIN], here’s a similar.)

Shoes – Michael Kors

Bag – Burberry

Finding Your Personal Style

When I was in high school, I wore what my friends wore. This was pretty standard for the time. We copied each other for everything, which is probably why we all looked terrible. We didn’t have Instagram for reference.


The uniform!! Me and my brother on my first day of high school.

I went to a Catholic high school, so I wore a uniform most days. I didn’t mind that so much, but for my early years in high school, it meant I had no kind of personal style. At all. I had few chances to examine it, and no desire to pursue it, because here’s the thing: out of my friends, I was the chubby one. I had hips and boobs before most of my closest friends had them. If anyone else had to grow up as that friend, you’ll understand the feelings of self-consciousness and inadequacy that would come at the most inopportune times: sleepovers, mall trips, school dances. I tried to copy what my friends wore, and, well, that was ill-advised. Some of the trends in the mid-2000s, like low-rise jeans and the layered look, really did not work on me. But I tried them anyway because my friends wore them, and I had no idea what else to wear.


Low-quality pic, low-quality clothing choices. I went through a phase where I wore Lululemon hoodies a lot. Really, I wore hoodies in general a lot.

It wasn’t until late in high school when I began to think more about what I wore. Part of that came from making friends with people from different high schools, who had very different senses of style than everyone in my immediate circle. They inspired me to dress differently. I started wearing high-waisted skirts. I went through a phase where that was nearly all I wore. Don’t get me wrong, I still love and wear that look today, but it was all I wore.


Grade 12, beginning to get a better idea of what I like. Thought this yellow coat was very ~fashion~. TBH would still wear.

But again, I was copying others. I copied my new, cool friends to try and, of course, make myself cooler. I don’t have to tell any of you that trying to be cool is an endless, ridiculous pursuit and the truth is none of us are cool at all. This world is full of nothing but dorks.

I digress.

There’s nothing wrong with drawing inspiration from the people around you. Everyone does it. What I found, however, is it’s good to venture out on your own, and maybe try wearing some things that are different, things that only you like.

I began doing this when I left for university. I thought, okay, this is it. You’re in a new city, new school, and you don’t have a uniform. Figure yourself out.

I can’t talk about my personal style journey without talking about my body image issues because they are inexorably intertwined. I felt uncomfortable in my body and had no idea how to dress it when all I wanted was to hide it.

SHORT PSA: Magazine guides for “dressing your body type” are bullshit. I know I’m talking about learning to dress for your figure in this, but I mean wearing things that fit properly. Things that are comfortable. It doesn’t mean that you HAVE to wear boot cut jeans when you’re curvy or you HAVE to wear wide-leg jeans if you’re tall. Magazines tell curvy women they have to colour-block the living shit out of their wardrobe and thin women can wear boyfriend jeans and t-shirt and be effortless. Honestly. Dressing for my body became a big thing for me. At the end of the day, rock whatever the hell you want.


My personal style changed so much over the course of my undergrad degree. I had a lot of influences come at me at once: new city, new friends, becoming fully immersed in Tumblr and Instagram and the beginning of my attention to style blogs and alternative fashion magazines (i.e. not monthlies).

Even now, as a post-grad, my personal style continues to evolve. At this point, I have a vey hard time describing it because it can be anything from a teenage delinquent from a 1988 movie to a cool librarian.

Even looking back to my first year, I cringe. I cringe when I look back at 13-year-old me and I cringe when I look back at 18-year-old me.


The red jeans. The red jeeeeaaaans. And no, I didn’t just wear this for school spirit functions. No, I wore these all the time.

18-year-old me thought red jeans were a good idea. I don’t know her.

The point of this ramble-y history is that I kept trying. Once I actively started to build my personal style, I kept trying different things, sometimes with success and sometimes not. Through it all I began to slowly (very slowly) gain more confidence in myself.

I couldn’t say confidence affected how I dress, or how I dress affected my confidence. I think the two feed off of each other. My self-confidence was and is affected by so many different things, but ultimately, building it up came from me, and learning to actually like myself.

I’m not saying you can’t wear clothes properly until you’re completely at ease in your own skin. The crappy truth is, it can take a long time to get there. We have perfection shoved down our throats these days. It’s hard. For me, a way to navigate that came from dressing how I wanted to dress, and feeling good in my clothes.

And, I won’t lie to you, every time a friend said to me, “You always look nice,” or “You really pull that off well,” it gave me a smile for the rest of the day.

So, that all being said, I have a couple of tips for those searching for their personal style.

I feel as though these may seem obvious, and I don’t want to sound like I’m talking down to anyone. These are very simple tips, but a lot of them are things where, once you start to consciously think about them, it becomes easy to shop and style yourself.

Start Small

We are not on What Not to Wear. Most of us don’t magically have thousands of dollars to drop on a brand new wardrobe. And trying to think of your style as a whole can be overwhelming. When you’re shopping, just focus on one item at a time. Find something you really like. Get it. Look at the clothing you currently have. Donate items you never wear and think about why you never wear them. Consider your favourite, most worn pieces and make note of what you like about them. This all sounds very simplistic, but that’s what finding your style can be like. Simple and gradual.

Get Ideas

As previously stated, I get a lot of inspiration from my friends and my environment. If you have a friend, co-worker or even a family member whose style you admire, ask them about it. I’d advise against copying look-for-look, but ask them where they shop, or where they get their ideas from.

In the nature of full disclosure, I said don’t copy entire looks off of people but I have definitely seen outfits on Instagram that I have worn head to toe. There’s nothing wrong with that. Social media is a great place to draw inspiration. What’s always the best, though, is to take an outfit you like and make it your own. Do as I say, not as I do, kids.

Examine Your Own Patterns

When you’re building your wardrobe, item by item, it helps to take an inventory of your shopping patterns. What are your favourite stores? What type of clothing are you the most drawn to? What colour palette? What material? Try and be self-aware in your search, so you can get a better grasp on what your taste actually is.

Size and Fit

THIS. THIIIIIS. I can’t tell you how important these two things are. Again, very simple, but underrated in my opinion. Here’s something it took me years to learn: the number on the tag of the pants you buy doesn’t matter. It really doesn’t. What matters is they fit perfectly and make your butt look amazing. It’s so important to try things on when you shop, as awful as that experience can be. Try and try again, size up and down as you need to in order to be comfortable in what you wear. Trust me, if you wear something uncomfortable or wrongly sized, it will be noticeable and that’s not a good look on anyone.

Trust Yourself

It’s great to get second opinions from people you trust. Sometimes if I’m unsure about something, I’ll ask my sister or my friends to weigh in on the dilemma. Sometimes we do need someone to tell us when something looks bad. Second opinions are great, but trust yourself above everyone. You know what you like and you know how things should fit your body. I do work in retail so take this with a grain of salt, but especially don’t trust sales people. I like to think that we’re all honest in the fitting rooms (I try my best to be), but some clothing stores are really all about selling, so they won’t always give the best advice. If they’re pushing you to get something you’re unsure about, don’t get it. If a friend isn’t a fan of a dress that you really love because it’s not their thing, then get it. You are your best critic.

Rock It

Wherever you are in finding your personal style, work with what you have. Feel good in what you wear and it will show. It sounds cliche, but nothing looks better than that.