Items You Should Invest In

This is a tricky one. There’s a good chance that you own multiple pairs. We do too. So you don’t need to invest a lot in every single pair, unless you can afford. But we do recommend splurging on one nice pair. Maybe that’s the pair that you dress up more so than your other jeans.

Try not to just dive in too quickly when spending more on jeans. Do your homework so you can make a good decision on which pair you want for the long run. And we recommend buying them in person so you can try them on and get a feel for the fit and fabric.

Some recommended brands: Naked & Famous, 7 for all Mankind, Raleigh Denim

When you put on a suit, you feel like a million bucks. The quickest way to ruin that feeling is by putting on cheap and run down dress shoes. There are two reasons why you should invest in quality dress shoes; they will last a long time if cared for properly, and they’re far more comfortable that cheap alternatives.

Higher quality shoes are generally made from full-grain leather, which lasts much longer than chemically treated leather that shows wear and tear pretty quickly.

Style wise, aim for classic look instead of trendy. This will ensure that you still like the look of them 10 years down the road.

Some recommended brands: Allen Edmonds, Church’s, Alden

If you can afford it, you should seriously consider buying a bespoke or made-to-measure suit. When you spend money to have something sculpted exactly to your body type, if feels amazing. Those who have gone this route know exactly what I’m talking about. For a custom tailored suit, the pricing will run a bit higher than a made-to-measure option, but you can’t go wrong with either.

If you must buy an off-the-rack suit, invest more money into the tailoring. And I don’t mean just getting the pants hemmed. Take it to a tailor to make whatever proper adjustments they recommend. It will absolutely be worth the money once you wear it. And like denim, every suit don’t need to be custom made, but shoot for having at least one go-to that shines over the others.

Some recommended brands: Indochino, My Tailor Store, Alton Lane, or ask your local tailor

Similar to dress shoes, you want to go for quality leather here that ages gracefully. With proper care, boots will hold up well over time through the harsh winters, against the snow/sleet/salt/etc. We’re talking 10-20 years. That’s a long time, which makes spending, say $400, not seem like that much over that time frame. As just like shoes, go for a classic look over a trendy look.

Also worth noting, is look for boots that have Goodyear welting. This will ensure that, over time, your feet stay cool and dry. Check out this video for a better description of how Goodyear welting is done and the benefits.

Some recommended brands: Thursday Boots, Oak Street Bootmakers, Timberland

While dress shoes and boots certainly fall under this category, if you’re in the market for any leather goods, it’s worth spending a few extra dollars on for the quality. This includes wallets, bags, belts, watch straps….you get the point. Cheap leather looks awful as it ages, and then you have to spend more money to replace it. Aim for quality and you don’t have to replace nearly as often.

Here’s a good run down on how to examine quality leather.