My past two days in attempted style. I think taking self mirror pictures in the tailor shop is an all time low for me. Warning: Spoiler! (Click to show)
Firstly, IV, I think you've come a long way from your early days here. Gone are the times of looking like a try-hard fraternity kid who wandered into his dad's closet. Good on you for the evolution. You seem to be making your way into a classic haberdashery sort of style. It's very unique for these times, and it almost always results from someone working (or being raised) in a traditional menswear retail environment. As Bill has stated in the past, % is the best example of a honed haberdashery style. Bits and pieces from here and there that might stick out at times or initially mark a fit as awkward, but, at the end of the day, somehow inconsistencies are eclipsed by the sum of the whole. I hope you will fully commit to continuing to learn and I'm intrigued to see where you go from here.
I think it needs to be remembered that he works in retail. All menswear retailers (from Sid Mashburn all the way down to Men's Warehouse) have a certain style or tone that they like their employees to adhere to. Having seen what others in his shop dress like, I think SS fits into his shop's environment quite nicely. One of the most underrated aspects of style is appropriateness and awareness of one's surroundings. While his looks aren't meant for the boardroom, they accomplish the goal in mind when put together.