Wheeled carry-on bag, $475 by Filson
It's no secret that good things often carry heavy price tags. And as someone who prides himself on hardly ever paying full price on anything, the idea of having to pony up some serious dollars to buy just one thing isn't an easy pill to swallow. But then you realize that some things are simply worth the price. For example, a sturdy Filson suitcase or a pair of Alden Indy Boots. Both items are hardly ever discounted, and for good reason—they're timeless, built tough as hell and hardly anything about them has changed throughout the years.
$479 by Alden
Sure, I could've tried to track down a used piece on eBay for a deal, but nothing beats the feeling of accomplishment you get when you're making something into your own. A perfect-fitting boot will get scuffed up and worn down over the years, and even the toughest suitcase will get dinged up during travel. But at least I know the imperfections are my own. They tell my story, not someone else's. And to me, that's worth the investment.