For the windowpane, look for a medium blue with a slightly broader line in either barker blue or a brown shade. Consider solid medium brown as well.
I feel that herringbone should be of a sufficient scale pattern to have the sportiness of an odd coat. Tight small patterns are too refined, for me.

 

Hi Tdiddy,

Your post sounds like you already have a pretty good idea of your style and what you are looking for. Pics are always very helpful to give us a good idea of your choices.
I just wanted to chime in as someone who likes the windowpane sport jackets. For me, I don't mind wearing a somewhat louder jacket regarding colors or patterns but when I match these up I tend to go for a much simpler look in the rest of the outfit. That is, I tend to wear solid pants, shirt, tie and pocket square or at least ones with minimal pattern. This allows the SC to stand out on its own and keeps the outfit from getting too busy. On the flip side, when I wear solid sport coats I will open up pattern in the other items.
I am still working on this myself as I try and determine my own style but one of the things I have noticed is that the higher the number of complicated pieces I try and combine, the less likely I like the final product. As a result, I am working on trying to add texture instead of pattern to the various parts of my wardrobe.

 

If you go the MTM route look at the w Bill Lamlana cloth. It is Cashmere-like and is wearable 12 months of the year by most individuals. There are window panes, herring bones, birds eyes, plaids and solids.
Paul Winston
Winston Tailors/ www.chippneckwear.com

 

Thanks for the feedback, that Lamlana looks pretty nice, I wonder if my tailor can bring it in.

Would the Dormeuil Iconik tropical 280019 shown here (https://www.dormeuil.com/en/cloth-c...tailed-collection/?reference=&composition=&couleur=BE&poids=&design=CA&qualite=) be too suitish for a sport coat?

 

^ I think that would be fine for a sport coat. It's a nice pattern and the color is pretty versatile.

 

So tailor talked me out of tropical wool blue windowpane and into black and white houndstooth from Holland and sherry. He thought it would be more classic and add more versatility to wardrobe, plus last longer.

Also decided to get a medium grey glen check suit that I am pretty excited for.

I would bet that most here would agree with him re black and white sport coat? Wondering if I should stay on this conservative bent in the future and get another navy blazer, darker this time. Right now my navy blazer its the only real odd jacket that goes well with the finer shirtings and silk ties I have.

 

It appears that you live in Canada, eh? I would think that you'd get a lot of mileage out of the Harris Tweed. Harris Tweed is also classic.