September brings a really exciting energy to the city of Toronto: TIFF Season.
With all the movie premieres happening, the celebrities slated to hit the city, and those after parties that everybody wants to be at, Toronto is the place to be.
We know that when it comes to the red carpet events and the parties, all eyes are on what notable female star wore which outfit better. While that kind of superficial analysis isn’t really important – feeling confident and having a great time is.
When it comes to being a man, and specifically an eligible man such as yourself, you can’t neglect your outfit when you’re out to schmooze. Having a look that draws the eye, prompts a compliment, and opens a conversation is an important strategy to making the most of your party time.
This month, we’ve got 4 style tips that will help you look your best, whether you are on the red carpet, or just wish you were.
Get Elevated With a Blazer
The absolute worst feeling is showing up at a party or event and realizing you’re underdressed. That’s a serious mood killer that will make you want to shrink into a corner and disappear. I (Jonathan) remember an occasion when I was on my way to a networking event and made a last minute decision to go casual.
Big mistake.
When I showed up at the event in a button down shirt and jeans, almost everyone in the room was in suits, and I felt like a little kid who was definitely not prepared to play with the big boys. I knew that I had way more to offer professionally than my appearance portrayed, and I felt the psychological hindrance of being unprepared.
Never let that happen to you.
The solution? Wear a blazer.
Blazers are the casual cousins of the suit jacket, usually cut a bit shorter, and meant as a jacket you can wear indoors and out. It almost doesn’t matter what else you are wearing, if you add a blazer to your outfit, you’re good to go and no one can accuse you of being underdressed.
Notice in the examples below that the looks go from jeans and a t-shirt, to a classic white button-up and tie. All of these looks are still casual and comfortable, but look elevated and cool. So even if you’re the kind of guy that can’t stand the thought of wearing a suit…consider adding a blazer to your casual wardrobe to make sure your look schmooze-worthy.

Add a Dash of Flash
Even if you’ve got your trusty blazer on and you’re feeling pretty suave, you still might be coming off as an invisible background actor, rather than a leading man. The key to making your look pop is by adding an accessory or two.
The image below pretty much shows all your options: pocket squares, ties, bracelets, boutonnieres, glasses, and a watch. Socks and shoes have been gaining leading roles in recent times as well. While you don’t need to go all out like these two gentleman, one or two items can do the trick.
The key in accessories is to express your personality.
What do you personally like? Metals with clean sleek lines? Earthy fabrics like leather that are warm and soft? Bright colours? Funky prints?
A personal friend of ours wears a watch that is a family heirloom, and often pocket squares based on famous Italian paintings. The compliments he gets, and the back stories he can tell are exactly the opportunity he uses to start a conversation.

Them Shoes Though
It’s said that women always notice the shoes…and we’ve yet to meet a woman who denies this.
The importance of shoes in social situations may be lost on most men, but it really comes down to paying attention to details, taking care of belongings, and seeing the big picture.
Once someone gives you the up and down, notices that ballin’ custom blazer, catches a glimpse of that classy time piece on your wrist…and then sees some scuffed up old Skechers on your feet…it’s game over.
Your shoes have to support the whole outfit. And this is where things can get tricky if your style skills are at a beginner level. With so many different shoe options, how do you know which to choose?
To keep it simple, new or “lightly” worn shoes will work for you. If your shoes are “well worn” or you have had them for years, there’s a 100% chance that they are wrong for this event or party.
Next you need to identify if the shoes are casual, semi-casual, or formal. That’s a whole blog post on it’s own, but in short, shiny shoes made from expensive leather with a heal are formal, while shoes with rubber soles and a more matte finish are casual or semi-casual. If you’re wearing jeans or chinos, go for casual or semi-casual shoes. If you’re getting into dress pants or full suit territory, go for formal shoes. The underlying principle is that the style of shoes need to match the style of your overall outfit.

Fit for a King
Finally, there’s the fit.
You’ve probably heard about the importance of fit before, but if for some reason you are resisting this timeless rule because you want to feel “comfortable” – we’re here to remind you that you’re being stupid (in the nicest way possible).
Dressing in clothes that don’t look smart and tailored make you look like a boy who borrowed daddy’s suit – and there’s nothing eligible about that. Since no one’s going to tell you that to your face, it might as well be us.
Your shirts, pants and jackets don’t need to be skinny and restrictive, but they should be snug with some give.
Compare these two red carpet looks. Silly moustache aside, Clive Owen doesn’t look at all like the accomplished, talented actor he is – with some truly badass roles on his resume. Tom Hiddleston on the other hand, an equally talented and rising star, knows that he is going to be photographed and decides he’s going to show up with his best. As they say, a picture is worth a thousand words.

Show Your Eligible Self
While it is true that skill and talent go beyond self-presentation, to quote Charles Hix, author of Looking Good: A Guide for Men: “Looking good isn’t about self-importance, it’s about self-respect.”
This September, show yourself some respect, and when you’re schmoozing, make sure you look the part of the eligible man you are.