I apologize for the overbearingly dramatic title. I also did consider posting in a "boot" related thread but felt it would be more productive to post it as a thread itself. Let me first put myself into context: I am a college student and have long yearned to purchase a boot of quality. Through several semesters, I have finally saved enough funds to do so (with around $500 USD.) In such perspective, I am not taking this purchase lightly as it is quite expensive and hope that the purchase will be a lasting one. I have been drawn to aesthetic and perceived quality of two particular boots at similar price points (other suggestions are welcome): the Alden 405 Indy in Dark Brown Chromexcel and the Oak Street Bookmaker Natural Captoe Trench Boot. In this thread, I would like to draw considerations and comparisons to the following: - Aesthetic - Quality - Comfort (or Fit) - Durability As I have never handled either boot, I cannot make such comparisons and hope those who have had experiences with these particular boots may be able to shed some light. The most I can say, in terms of the aesthetics, is that I do prefer the iconic look of the Alden Indy to the Trench Boot. I find the contrast-stitching makes the boot wholly more distinctive to the trench boot; that is not to say that the trench boot is generic, but rather it is more subtle in aesthetic expression (when compared to Red Wing GT/Beckman and Wolverine 1K Mile Boots.) Now "more matter with less art", I hope you guys will be able to assist me in my future purchase.