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100th Post! Prince of Wales

November 6, 2015 6 Comments

Hey friends! I’m Jocelyn’s photographer, boyfriend and best friend, Azim. We’ve had so many requests from both girls and guys to showcase some of my own personal style. Menswear deserves some love too!


So, I literally picked the best time of year to start posting outfits on Jocelyn’s blog. Fall is probably my favourite season and that seems to be common with a lot people I talk to. With temperatures fluctuating between 10 to 15 degrees, us guys have the opportunity to layer up without having to throw that parka on and blanket all of our hard work.


Being in my mid-20s, I’ve noticed that my blazer game has surged overnight. What used to be mostly athletic wear has been replaced (And no, that’s not just Jocelyn’s influence 🙂 ). I’ve got my pick of different patterns, colours, and materials – I cherish them all. This particular, glen plaid blazer is part of a suit that I bought from J.Crew. Interesting note: glen plaid is sometimes nicknamed “The Prince of Wales”, as it was popularized by the Duke of Windsor during his tenure as the Prince of Wales (hence the title of this post – I am clever).


I really like the way a light blazer pairs with a slim pair of dark-wash jeans. The beige, linen tie was actually a last minute decision. Jocelyn gets the credit for that call.


The University of Toronto’s Hart House is beautiful this time of year. Fall colours and mild weather mixed with incredible, old architecture make for a great photo shoot. Inside the building is equally, if not, even more stunning – we’ll save the inside for a future outfit post.

IMG_0367-1IMG_0394-1The outfit itself wasn’t really inspired by anything in particular – normally it comes down to if it looks right and feels right, then walk out the door. I think I did alright. Comment and tell me what you think of my first #OOTD! Happy Friday!

Blazer – J.Crew / Shirt – Club Monaco / Tie – J.Crew / Sweater – Joe Fresh / Pocket Square – Scotch & Soda / Jeans – GAP / Socks – Happy Socks / Shoes – Donald J. Pliner


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  • CJ November 6, 2015 at 1:15 pm

    Very sartorial look my friend. J.crew has a great selection of blazers so you can never go wrong there. Wifey made the right on the knit tie; all in all wicked ensemble man. I’m curious though as to why you didn’t highlight the double monks, those are fire.

    Excellent photography as well you two, keep it up.


    • jocelyncaithness November 6, 2015 at 8:53 pm

      Thank you so much, CJ! That means a lot, coming from you 🙂 Next time I will make sure Azim highlights the shoes – they are always my favourite part!

      Keep in touch xo,

  • Zahra Nurmohamed November 6, 2015 at 1:55 pm

    Congrats Jocelyn.!! Your “Prince” is quite the Prince of Tales too!! Azim- love the look. You must have inherited your fashion sense from your incredibly talented aunt from your mum’s side. I’m loving the look that you are rocking. Since it is the fall, next time I suggest you accessorize the look with a pair of Chelsea or Chukka boots. My beloved is not that fashion forward but you certainly are!! #ohtobeyoungagain

    • jocelyncaithness November 6, 2015 at 8:55 pm

      Thank you Zahra!! You are absolutely right, we all know where Azim gets it 😉
      Funnily enough, we’ll be featuring a really cool pair of Chukka boots soon! And I am dying to get my feet into a pair of Chelsea boots (eyeing the ones at J.Crew)

      Thank you for reading, and for commenting. It means so much to us, as we work really hard to put the content together <3

  • Margarita November 6, 2015 at 3:09 pm

    Very well written and made me chuckle 🙂

    • jocelyncaithness November 6, 2015 at 8:56 pm

      Thank you Margarita! Thanks for reading, it means a lot to both of us!

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    About Me

    About Me

    Hi, Friend!

    I'm Jocelyn: a daydreamer and fashion lover disguised as a finance professional. My head may be in the clouds, but my stilettos are firmly planted on the ground ;)

    Jocelyn Caithness

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