I know this topic has been debated quite frequently in the past, but for any style-conscious gal, this is still the age old question. So here's my story: Prior to my MBA, I worked for a creative company which owned several fashion magazines. Of course, I owned all but one pair of Louboutin's and I was not about to "waste" them at work. Looking back it would have been the best place to wear them, because it was like NYFW everyday at that place! After my MBA I landed a position with a Management Consulting firm, and I was often conflicted about wearing Louboutin's to work. Right in the heart of the financial district in Toronto, I didn't know if it was overtly fashionable. Currently, I am back to working for the HQ at a major retailer head office. I completed my Master's in Public Health and work in supporting the Clinics & Pharmacy practices. Although the company is young, fresh and hip, I work in healthcare, were my direct colleagues are pretty 'stiff''. Spending so many hours a day at work, I would love to wear these shoes, that I quite frankly spent a ton of money on! But, I already have some of the Pharmacy Consultants here poking at my bags, telling me, it must be so nice to be young (I think they think I am younger than I really am), and not have any responsibilities. So would wearing such identifiable shoes elevate and increase that type of commentary? It's annoying because I have always worked so hard! I've had great parents who supported me, but 85% of the time, I have wanted to do everything on my own. Paid for my education supported charities and made good investments. So what if I spoil myself every now and then? But how do I explain this to judgmental people at work when they see the red soles walk by their desk in the morning?