I want to jump in here because I think that I can cure some of the dilemmas that one might have by merging designers / looks together and not look like a bag of balloons.
When I got into this business in the late 70's there was a confluence of designers vying for the spot light but two many were too special. Armani, Versace, Montana, Ferre in one camp, Lauren, Ellis, Julian in another and people like Westwood and Paul Smith sneaking in. These are just to name a few but all with different points of view. This point of view, as a sales consultant, was a determining factor as to a direction in which we would help establish ones look. I was at an advantage, having been a student of Art and Design, I was able to utilize the fundamentals of Shape, Color and Texture and apply them to what I visually created as outfits.
Women seem to pull this off seemingly naturally but they also are digging relentlessly and ruthlessly to bring together the latest and greatest. By digging, I mean they are doing there homework by studying.
Magazines, magazines, magazines. Reading them and paying attention to whatever the media is suggesting is happening.
I'm not that familiar with Tegers looks but from what I have seen, he has a pension for the skinny. Does that work with suggested topic, I think so in some cases. My critical eye would say no if he were to attempt to meld Engineer Jacket with BoO Shirt. Boxy Jacket / Skinny Shirt - Round Hole / Square Block.
My best advice would be to experiment with your wardrobe, "which I know" is an Oxymoron for a guy. Pull everything out of your closet and start mixing things that you normally wouldn't. Your eye will eventually tell you yes or no but if it's not comfortable the first time and your unsure, try it again on another occasion, you might have a different opinion. I call this the emotional relationship between you and your wardrobe, sometimes it works, sometimes it sucks, it's the bitch in all of us.
Another lesson I always suggest to my clients is to study mannequins in every store you go in, they are the silent salesman, that tell stories and give us ideas. I always benefit from these because it's a "Duh" experience. Like, why didn't I think of that???
WAYWT would be good place to get critiques of looks your unsure of but beware of the uncharitable.
I could go on but need to get to work. Challenge yourself. Fail. Learn. We might call you Bozo but at least you've achieved that. Later!