Apologies for the overly ponderous thread...but have any of you ever felt really satisfied with your wardrobe? Or is it just a constant sense of what you need next, or how you could upgrade? I'm 30, I've had at least somewhat of an interest in clothes for the last 10 years, which has picked up lately, culminating in my joining SF. I've already spent more money on clothes than 99% of American men will spend in their entire lifetimes. There are many, many items I own that I love dearly and wear proudly. But I wouldn't say that I'm satisfied with what I've got - in some ways I just feel overwhelmed with the "next level" above - Armani Black Label suit? Isn't Kiton better? Kiton RTW suit? Why not get an Attolini MTM? Why not go bespoke? Then once you're going bespoke, there are so many options for tailors and fabrics...the expense, in terms of both money and time spent contemplating all the options, is massive. Yet once you're aware of all the possibilities, it may be difficult to be satisfied with anything but perfection. Is ignorance bliss? If you could eradicate your good taste and appreciation of high quality items and live happily in a $50 pair of khakis and a $30 polo for the rest of your life, would you do it? Is the happiness you get from your appreciation of your favorite items worth the trouble you take to maintain your wardrobe, consider ways of expanding or editing it, and the frustration you feel at not having everything?