The listing below is my running tally of BIFL (Buy It For Life) or at least BIFRLT (Buy It For A Really Long Time) product recommendations.
To read more about the BIFL product culture, check on my blog post here.
These are long-lasting khakis, which are great for office work. With the right care, these can last for years. Read the blog post discussing these pants here.
These are long-lasting leather birkenstock shoes, which I wear almost every day to the office for business casual dress. With appropriate resoling, these should last quite some time. Note: I would recommend getting them resoled with a vibram rubber sole, which I talk about in this blog post.