Style Inspiration – Jonathan Cavaliere

Jonathan showing his dapper side

That Dapper Chap interviews Canada’s Sharpest man. Stylist, blogger and style inspiration: Jonathan Cavaliere

Meet Jonathan

Jonathan is the guy who has inspired me to be where I am today,he ignited my interest in menswear and set me on my sartorial journey. 

While looking around on the web for one thing or another I happened upon his blog, I read a bit, I read a bit more and the found myself searching for items that he has featured on his blog for me to wear to emulate his style. If that’s not inspiration and makes him the best person for my very first ‘StyleSpitation’ feature I don’t know what is!

The Interview

TDC – How long have you been interested in menswear and
who or what inspired your interest? 

JC – I have probably been inspired by menswear since I
was 10 years old. At that age, it was more about a search for the man I wanted
to become rather than just clothing. I idolized many different people whether
they were actors, athletes, or people on the street, but I always found one
common denominator, they all dressed well. At the age of 17 I started working
in retail selling men’s suiting. Not knowing much about suits at the time I was
determined to learn everything I possibly could which would allow me to be one
of the best at my job. As the years went by I slowly honed my skill and
menswear became more of a passion rather than just a job.  

Looking smart in monochrome

TDC – That learning has really paid off for you! Congratulations on becoming Canada’s
Sharpest Man. I voted for you a number of times. Has it opened many doors for you? Is fashion your
career now? 

JC – Thank you! Being crowded Canada’s Sharpest Man more
than anything gave me the backing I needed to pursue a career in a female
driven industry. Females whether its womenswear or menswear dominate the job
market in Toronto and before winning my sartorial accolade I always found
because I was young, male, and heterosexual there wasn’t going to be a place
for me. Once I got the title I was contacted by many brands and guys who wanted
to know my opinion on different menswear related topics which I feel in a way
opened the door for other guys who want to pursue fashion as a career! The fashion industry is one of those career paths
where you can dabble in so many different channels. At the moment, I am
blogging on full time, but I also do men’s personal shopping
and image consulting on the side as well as creative direction for local
menswear boutique.        

The winner of the Canada’s Sharpest man competition

TDC – I’ve seen a few styling projects of yours.
Is this the way forward for you? Personal stylist?

JC – At the moment personal styling and blogging have
been awesome and brought up some great opportunities. The guys that I help on are very grateful for my services and a lot of the time I
feel like the only reason I put in the extra work is because of how
appreciative my clients are. At the end of the day though you never really know
what the future holds.


The Mr cavaliere Blog

TDC – So, you’ve styled many guys, but what is your ‘go to’ look

JC – Well this depends on the season and the occasion of
course, but I would say a white club collared dress shirt, my blue plaid wool
waist coat, a grey tweed blazer, a paisley pocket square, royal blue chinos, a
printed sock, and my navy wingtip boots. 

TDC – You mentioned colour, pattern or texture there but if you could only have one which would you prefer?

JC – I would definitely choose pattern. Pattern is one of those elements of dressing that guys stay away from but is ultimately the difference between a good look and a great look. Pattern can be as striking as color and can be confused for texture. It’s truly the secret that gives your outfit depth and visual interest.

Jonathan in a more relaxed style with camo patterned joggers

Stan the Mannequin, styled in pattern by Mr Cavaliere

TDC – You’re clearly on your A game, you must consume fashion every day. What would you
recommend to my readers?

JC – I read about men’s fashion to keep me up to date on
what’s going on and sometimes even to inspire my own look. Most of the fashion
literature I read is from the internet. Blogs and online magazines are the best
source of up to date information as you can interpret it through the likes of
picture, words, and video. Some of my favorite sources are,, and  

Jonathan embracing colour

TDC – If you could have one fashion wish what would it

JC – If I could have anything it would probably be a
custom bespoke glen check 3-piece suit made to my exact specifications.

TDC – I’m with you on that one! Now lets flip that around; what’s your pet hate in menswear? I know at least two of them!

JC – I actually have quite a few but if I had to choose
one it would probably be tying your tie abnormally short. I’m not talking just
above your belt buckle, I’m talking about those guys whose bottom two buttons
of their shirt are exposed because their tie finishes in the middle of their
sternum. Chances are if you don’t take the time to tie your tie to the proper
length the rest of your outfit was put together with the same carelessness. 

Wearing the perfect length tie

TDC – Good advice on the tie! but what advice would you ofer to someone who came to you for help with an outfit for a summer wedding?

JC – The great thing about dressing for summer weddings
is that you can have a little more fun with fabric and color. I would do a slim
beige cotton suit, a madras printed button down collared shirt, a navy knitted
tie, a solid colored tie bar, a linen brown tipped pocket square, a braided
belt, and a suede brogue. It’s breathable for the summers warm but smart enough
that you won’t be underdressed.    

TDC – Duly noted! I have two weddings coming up very soon! Time to go shopping! I’m staying over for one of them so what three essentials would you suggest that I pack in my case?

JC – I don’t classify myself as an expert on packing but
there are a couple of items I won’t leave without. I always pack great
underwear first when I go away. I think there are a couple reasons why I do
this. Firstly so I don’t forget it but secondly so I am comfortable where ever
I am heading. Sometimes being away from home can be a pain and having comfy
underwear can be exactly what you need to make everything a little bit more
bearable. Who knows you might get lucky and at least you’ll be prepared! 

second item I bring is my leather Roots tote bag for all my toiletries. There’s
something about this particular bag that I love, It could be that I carry a
little piece of Canada with me no matter where I go or that I got it for free
but for some reason it’s always there for my various travels. Lastly I can’t
leave without my hair product. I use Schwarzkopf Got 2 b glued because it has
the perfect hold on my pin straight hair. If you’ve seen a lot
of my looks compliment a cleaner hair style and for this reason I can’t settle
for a product that won’t give me the hold I need. So I never go away without

Raising the smart level of chinos with a double breasted blazer

TDC – You mentioned ‘getting lucky’ So, It’s your first date (not that you, as a gentleman, would expect to get lucky on your first date of course)but she’s booked a table
at a local restaurant, what are you going to wear other than great underwear?

JC – On first dates I like to dress inconspicuously, but
fashion forward at the same time. The reason why is because first dates should
be about letting your guard down to allow yourself to get to know the other
person and your attire should represent that. 

I also never wear a tie on a
first date, and there are two reasons why. The first reason is related to the
letting your guard down theory, it allows you to get to know the person without
you looking like it’s a serious business meeting. The second reason is because
it shows off your collar bone. Your collar bone is a place on your body that doesn’t
build fat and when seen, it gives the illusion that the rest your body is just
as chiselled as your exposed chest bone. Don’t take it too far though two
buttons maximum. 

With this being said I would probably wear a button down
collared shirt, a solid colored cardigan, a denim jacket, navy chinos, and a
casual sneaker or leather boot. 

Jonathan, date ready?

TDC – Your wardrobe can’t just be full of great pieces. What’s the most horrible thing you own that you
just can’t get rid of?

JC – I own these black Adidas trainers that are
destroyed and for some reason I can’t throw them out. I wear them when I’m
cutting the grass or going to get the newspaper as they literally tear at the
seams. It’s probably because they were the first shoes that I really wanted as
a kid that my mother actually got for me! I usually would get an option between
two pairs I didn’t like and would have to wear them till the sole fell off. This
deprivation of shoes I liked may be another small reason of why I got into fashion!

TDC – We all have something like that. With that in mind, what advice would you give to a young man who
wasn’t sure about his style and what choices to make?

JC – A lot of people say start with the basics but I
feel you should start with what not to wear first. 

One of the first posts I did
on was a what not to wear post because I think it’s more
beneficial to know what not to buy before you go spending your money. 

In a way it’s
like un-teaching bad sartorial choices so there is room for new good wardrobe decisions.
After you’ve taken the menswear rules into account, then it’s time to start
investing in your essentials!

TDC – Great advice! I know that you’ve done various collarerations and I’ve seen video of you too (see below)but what’s next for Mr Cavaliere?

JC – At the moment I am just working on making as good as it can possibly be. Like anything that’s worth it,
it takes a lot of time and commitment and hopefully one day the Mr. Cavaliere
can be a recognised style source for all things menswear related.

At the end of the day you never know what the
future holds that’s why I just taking everything one step at a time! 

I’d like to thank Jonathan wholeheartedly for not only being the subject of my very first StyleSpiration piece but also for being my initial inspiration which has taken me to where I am today. Check him out and I’m sure you’ll be inspired too.

Find Jonathan