To continue to clarify genres of dressing.

Old Boy Hip is for the office. The most conservative companies in the USA will appreciate it. Maybe in England where the Fogey observer still has some power, the most modern accessories will be sneered at by him as arriviste but otherwise even there people appreciate the modern

Hip generally congregates around luxury, softness (it is in touch with the feminine, refinement, smoothness, even a bit of shine and gloss.  Although quality is demanded, longevity is not. Hip also embraces universal associations. There are no old school ties (although striped ties can be worn at the office in beautiful color combinations), no birthrights, there is only talent and the quality of being engaging.

On the one hand, hip can mean that an executive chooses the most traditional patterns and colors for suit shirt and tie but instead of 80s wool, he gets the suit mad in 150s, and for the shirt, instead of 100s cotton, he gets it in 220s and instead of a J. Press twill tie, a 7-fold, ottoman rib striped tie in a high silk count. Socks could still be Pantherella and shoes can be Edward Green but they might be from the contemporary range. There is nothing daring here, everything would on the surface meet  with the approval of the Fogey but the wearer is spoiling himself with a softness and a tactile sensation that also signals to his contemporaries and to  youth that he is successful and in step with what is current; not holding on to what is passed.

I think it also has to do with one’s mental state. If you believe you belong in the past or the past is superior, you might become fascinated with weights and materials and the type of finishes placed on these materials the past. You might even want to recreate it perfectly and wear vintage clothes. That’s fine by me, but it the great bulk of people who buy these clothes and interact with you will believe you quite odd and in a way that might not be good for business.

Everyone appreciates the occasional vintage piece, as Americans we love the old black and white films and a reference to them is fine but to make a meal of them you will be judged as very quirky, which may not be your aim.

And for Old-Boy-Hip there is a trade off between luxury and lifestyle. The reason old boy hip is not full fledged hip is that it has to appeal to a broad spectrum of people without offending any of them (Think of the President's clothes or newscasters clothes) and it has to take the office/work-travel pounding that business clothes take. So there has to be a balance between up to date-ness and performance.

For full fledged hip, generally you are either working in an environment where everyone you meet expects you to be modern and/or you are wearing the clothes for limited purposes. This is why  a suit in 220s wool might be hip for after hours or if you literally do nothing but get driven around town but I wouldnt recommend it for business. Sticking to the 100s-150s in 11-7.5 oz cloths is a better idea.