This was something I really struggled with early on in my career. I could design the coolest stuff (if I do say so myself;), but I would often get the feedback that it was "too cool". Huh? WTF? How can you design something TOO cool! I had to learn that when you're designing, particularly commercial fashion, it's important to keep the customer in mind. And if your customer is a bit more conservative in their fashion choices, you have to learn to tame that. Push a bit every season, but not push people over the edge! Because at the end of the day, you're working for a BUSINESS. And if the customer doesn't buy what you designed, it doesn't matter how cool it is. The business doesn't make money! (And eventually, you may not have a job!)

I believe it’s important to experiment with trends and be creative while remembering that some classic principles should always remain. For example, the tuxedo has a ton of tradition rooted in presenting the best look for evening events. I wouldn’t change that. The same goes for classic business suits. However, when it comes to more casual settings like cocktail parties and happy hours, it’s ok to go outside of the box and try new things with color and fit.

I personally think that market appeal in fashion can change in an instant, so I wouldn't over-consider it. Especially that new trends are made from exceptional designs that suddenly 'appeal' to the market. Additionally, I think that most fashion lovers are usually looking for unique designs that stand out from the crowd; rather than a trend that everyone is wearing. Bottom line: try to be creatively original, you never know what's gonna 'appeal' or not.

I think it is very important to meet the needs of you customer. Balancing creativity and market approach is the most important challenge that we designers have to manage. In the end a good design is sadly one that sells.