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Spoo,
you are a good sport so here goes. I'd get rid of all the sport coats and start from scratch. I'd also ditch most of the suits along the way. One of the main problems with your outfits is the fit and then the fact that you bargain hunt them and purchase because they are on sale rather than purchase because you actually need or want them. So,think about getting rid of all SCs and start getting something custom made,better fit and some fabrics that you actually want and like. Don't have 30 SCs,get 10 made up and wear them with more sedate shirts and ties. Same applies to your suits and shirts,I think you will improve significantly if you start getting something made custom,much better fit and pick the fabrics you want. You are in NY so you shouldn't have problems with access to good tailors and with the money you spend on clothing,you can afford to go custom.
Its great advice, really. Even if you are telling me to ditch my entire wardrobe
The problem for me with bespoke/MTM is the time. I am in NY, but rarely have time to put up a post here in the workday, let alone go select fabrics and get fitted. The weekends I have my own business to tend to, and I watch my kid on top of that too. I keep saying one day Im going to go ballistic, tell my wife to hold **** down for like 9 hours and do it all in one shot, then just keep my measurements on file and call in future projects, but I keep procrastinating.