What is your comfort level with style?
If you didn't grow up with a need to dress nice on a regular basis, I may feel awkward to put on a suit even for a special occasion. This was me until family recently. I own a business I worked by myself from home since My early college days and I'm not particularly social so there was no need to dress up. Staring law school forced me I to being social and compelled me to dress appropriately for the field. Despite getting well-fitted suits that I know look nice, I still feel a bit awkward especially in the trousers. The thin light material often feels "insufficient" (compared to the denim I normally wear) I can say I've gotten used to the feel, and despite a good fit, the material still feels somewhat alien. I suppose with enough exposure it will get more and more familiar. All that being said, the highest level of classy I would say is "comfortable" (in mind not physically) is nice jeans, dress shirts and sport jacket. What about you?