Most guys spend their lives making the practical choice—the less expensive shoes, the decent watch, the off-the-rack suit—and there’s absolutely nothing wrong with that.
But I also believe that if you’ve worked hard, handled your responsibilities, and have the money, there comes a point when you deserve to treat yourself. I’m not talking about spending money recklessly or buying things simply to impress other people. I mean upgrading certain things because they make you feel amazing.
There are some purchases that, once you experience them, make you think, “Damn, I wish I had done this sooner.” Some are expensive, some are surprisingly affordable, and some are completely unnecessary. But that’s kind of the point. Life shouldn’t always be about choosing the cheapest, safest, or most practical option. Sometimes quality, craftsmanship, confidence, and simply loving something are worth paying for.
You’re allowed to enjoy what you’ve worked for. Take care of your responsibilities first. Don’t go into debt trying to impress people, and don’t confuse spending money with success. But if you’ve worked hard, taken care of business, and can genuinely afford it, every decision doesn’t have to be the responsible, economical choice. Every once in a while, gentlemen, treat yourself.
You deserve to treat yourself to these
- A Semi-Custom or Properly Tailored Suit — You don’t necessarily need to spend thousands on a fully custom suit. A quality off-the-rack or semi-custom suit that is professionally tailored can look and feel incredible. Start with something versatile like navy or charcoal gray. Once you experience a suit that actually fits your body properly, it’s hard to go back.
- Your Own Tuxedo — If you occasionally attend black-tie events, stop renting somebody else’s tuxedo. Buying a quality tuxedo and having it tailored means that whenever you need it, you’ve got something that fits perfectly and makes you feel like freaking James Bond.
- A Special Watch — For me, it’s a Rolex, but it doesn’t have to be. I believe every guy deserves a watch that represents an accomplishment or important moment in his life. I engraved “Get to Work” on mine. Whether your watch represents success in business, becoming a father, reaching a goal, or simply realizing you’ve made it, it becomes more than a watch—it becomes a reminder.
- A Proper Jacket — Your outerwear can either elevate an amazing outfit or completely destroy it. Invest in a timeless jacket you love—a peacoat, leather jacket, field jacket, or another elevated option. A great jacket can become your signature piece and actually look better as it ages.
- Elevated Casual Pants — Casual doesn’t have to mean sloppy. I recently picked up drawstring cotton pants you can wear casually or with the drawstring tucked away so you can add a belt. The idea is versatility: comfortable enough to feel relaxed but polished enough to still look sexy and stylish.
- One Really High-Quality Sweater — Whether it’s cashmere, merino wool, a long-sleeve polo, or a great crew neck, experience what quality fabric feels like. Better clothing drapes better, feels better against your body, and instantly gives you a richer, more polished aesthetic.
- A Pair of Incredible Shoes — One of my personal choices is the Gucci Jordan loafer. Yes, they’re around $1,000, but they’re timeless, incredibly versatile, and built to last. I’ve had mine for about seven years and still wear them all the time. A great pair of shoes can complete an outfit and make you feel like a man.
- Quality Jewelry — Upgrade from cheap, mass-produced jewelry to something special. It could be real gold, quality silver, or a more customized piece. You don’t necessarily need something flashy; the point is owning something distinctive and meaningful that you can wear for years.
- A Great Pair of Glasses or Sunglasses — Do expensive frames work better than inexpensive ones? Not necessarily. Sometimes you’re paying for the brand. But there’s also something fun about owning a beautiful pair of frames from a designer or brand you really love. Not everything has to be justified purely by practicality.
- One Completely Unnecessary Purchase You Absolutely Love — For me, that was my Porsche. Did I need it? Hell no. Was it ridiculous? Absolutely. But I worked hard; it was something I had dreamed about, and when I finally had the opportunity to do it, it was worth it to me. Your unnecessary purchase doesn’t have to be a car. Maybe it’s a $400 wallet, an incredible pair of shoes, or something else you’ve always wanted.
