Style Inspiration – Jonathan Cavaliere

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

Jonathan showing his dapper side

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 be?

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!

The 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 it!

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. 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









Product Review – Oybo Socks It To ’em

That Dapper Chap reviews Oybo Untuned Socks.

One Pair, Two Souls


For this product review I’d like to introduce you to Oybo
Socks, an Italian sock brand that packs a punch in the ever increasing bold world of socks.

Disbanded Summer
I’m loving my Disbanded Summer Socks

Oybo are different both figuratively and
literally as the first thing you’ll notice is that their socks do not match!
This is their USP and they sell their products as ‘untuned’ i.e. each pair of
socks is a pair but each individual sock has a slightly different design to its

Some of Oybo’s latest collection
Me modelling Lemon Squeeze along side Sashimi
Lemon Squeeze and Pixel

The people at Oybo say “We’re a small group of friends who started to do something nice for ourselves. We loved it so much we’re now proposing sharing our enjoyment with connoisseurs who are serious about fashion but don’t take themselves too seriously! This is to the ones who enjoying telling the whole world what they’re about. And like doing it with nice details”

Modelling Pixel

The last couple of years has seen a sock revolution and you can now buy a huge range of multicoloured socks in a variety of designs. This is in direct demand from guys like me who want to inject some interest into their look on a daily basis. Wearing a bright and funky pair of socks is a sure fire way of injecting some personality and showing some individuality.

The majority of their socks are 95% cotton with 5% elastan. They recommend that they are hand washed and not tumble dried. They can also be dry cleaned.


I think you’ll agree that Oybo have taken this a step further and introduced a funkier element to the sock revolution and its one that I’m enjoying!



A pair of Oybo socks will set you back 22 Euros (£17 $30). For a pair of socks this does seem a little steep but the design that has gone into each pair is worth it. You’re not going to find anything similar out there and you will get noticed while wearing them.

Grandma, Versailles and Lemon Squeeze

These are a more high end sock. Buy yourself a pair as a treat or put your favourite pair on your birthday list.

Kobe Green


The Oybo packaging is great, I love it and it only adds to the fact that this is a high end sock. Each pair comes lovingly joined together with a cardboard tag before it is encased in tissue paper and them placed into its own cardboard envelope. The envelope has the name of the sock hand written on it which is a very individual and personal touch.

The printed cardboard envelope

There is a lot of information on the cardboard envelope about the product, the material and washing instructions. There is also a cute little note suggesting that while we have two feet which are the same, we may have mixed feelings, so why why not wear different socks.

Each pair is beautifully folded and tagged


A lot of Oybo socks are knee high. In the UK we’re used to something that finishes mid calf at the highest. This may be a little distracting for some gentlemen and okay, maybe you don’t want to be wearing a pair of Oybo socks when changing at the gym as you will get funny looks (I know this first hand)but the bonus is that they do not fall down. You pull them up in the morning and they stay there all day.

Baton Rouge, some of my personal favourites

Some of mine have been washed a few times now and while I have mentioned above they it is recommended that they are hand washed, mine have been in both the washing machine and the tumble dryer! (Sorry Oybo) I’m pleased to say though that they’re still good to wear but the colour has faded and they have shrunk slightly. So yes, the recommendation to hand wash them is correct!

They are easy to wear and the summer range are cool and airy. They are not too thick and have a weave a little like a ladies hosiery. Again, in the UK we’re not familiar with this but other countries are, and it’s expected. I’m okay with it but it is very different to what I’m used to. The ‘warmer’ range such as Pixel are a nice thickness and its good to have a choice of thickness when choosing socks.



If you work in a bank and wear a grey suit every day and have to meet incredibly important people while remaining perfectly professional, maybe you should stick to a plain black sock as these babies could distract from all those graphs and PowerPoint presentations!

If your’e a guy who likes to stand out from the crowd or who does have an important job but still wants to show some personality (as a lot of us do) then these are for you!

Me, ready for the office


The main thing I like about Oybo socks is the selection. They have a great range and I have never seen anything like them before. They stay up all day and they are very comfortable to wear. They do not leave you with those horrible ‘sock lines’ which reshape your legs and leave dents in your calves indicating that your circulation has been a tad impeded all day!

I’ve struggled to think of any negatives or anything that I’d change. I’ve already mentioned the light weave and the similarity to a ladies hosiery. This does make me a little uncomfortable but that’s just me being a typical Brit and I’m already getting over it. Other than that I have no suggested improvements!



Some people don’t get it! Some people think that I have intentionally brought and worn different socks in some misguided attempt to make some kind of awkward social statement.

Once I made them aware of the brand and their philosophy they get it, but they are still a little uncomfortable with the concept. Its not mainstream so some people find it difficult to get their heads around.

My test group liked the designs and the quality of the socks but the majority of them would not wear them, simply because they are too different.

Grandma by the sea


Its apparent that I’m a fan! I’m a person that likes things that are different, that stand out, and which challenge the norm. Oybo do this and they do it well and to a very high standard.

Not everyone is as comfortable with the concept as me and the person that buys Oybo socks is making a statement and showing the world that they’re happy to step out of a box.

They’re aimed at the individual, the person who is happy to take a risk and the person that is often found putting two fingers up to the world and saying “Yes, I’m different and I’m happy to be”

More of the Oybo range





Instagram: #oybofriends


My Oybo collection
Me wearing Disbanded Summer
Me with my collection

Thanks for reading!

Product Review – The Daniel Wellington Watch

Craig of That Dapper Chap reviews the Classic Warwick watch by Daniel Wellington.


Daniel Wellington were kind enough to gift me the Classic Warwick watch, this will be the focus of this review.

Established in Uppsala in Sweden, just an hour’s drive from Stockholm, there is a story about how the watch came to be and their website states: “Filip Tysander, the founder of Daniel Wellington, met an intriguing gentleman from the British Isles. The man had the inspiring ability to be gentlemanly but still relaxed and unpretentious. He had an impeccable style, and loved to wear his watches on old weathered Nato straps. His name? Well, Daniel Wellington, of course. A strong friendship emerged between the two, and our founder was inspired not only by the man’s many great life stories but also by his class and timeless style of fashion”.

I’m not sure how true this is as is reminiscent of The Great Gatsby story. A part of me likes to think it is, but only the people at Daniel Wellington know the truth about that one.

The Classic Warwick by Daniel Wellington

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