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There’s a good chance you’ve been told it’s not worth investing in basics like belts, socks, and men’s underwear.

“Stuff you use every day shouldn’t cost too much. What’s the point? You’ll wear it out anyway,” they say.

I even wrote a short article a few years back stating the same thing.

But today, I’m retracting that statement. I’ve lived a little. I’ve experienced a bit more. And I’ve realized this: in the long run, it’s often worth the investment.

You use these five things every single day. They directly affect your comfort level. So consider spending a bit more to get the best you can afford.

Here are five items that you probably skimp on… but I suggest you start investing in.

Luxurious Men’s Underwear

Like I mentioned earlier, I stated a few years back that underwear is something worth skimping on. I suggested that it’s okay to buy the cheapest stuff possible, because no one sees it anyway.

I guess that made sense to me at some point. But honestly, after spending a bit more on my boxer briefs, it’s made a WORLD of difference.

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What’s changed? Mostly, the fabric… which means better quality and more comfort.

Top-quality men’s underwear is made from luxurious, high grade fabrics like MicroModal® AIR, Micro Tencel®, and Swiss Cotton.

“High grade fabrics” sounds like an unnecessary luxury — until you try it. Great underwear feels like it’s not even there. Invisible.

On top of that, these fabrics are naturally hygienic, moisture wicking, and stretch-resistant. They’re also far softer and more durable than regular cotton.

Bargain-priced boxer briefs fall apart after a few weeks of repeated washing. They fade and stretch (even while wearing), completely losing their shape.

So you buy more. And more.

All the while, you’re never truly comfortable. The fabric is rough and scratchy. The seams are bulky and tight. They dig into your sensitive areas. When that pair of underwear finally softens up, it immediately starts coming apart.

My advice: Start with ONE PAIR of well-made men’s underwear. Just one. Live with them for a bit. Really get a good wear out of them. You’ll immediately notice the difference.

A Slim, Elegant Wallet

A wallet is one of the few things guys take everywhere. Even my watch — which sees frequent use — doesn’t go everywhere my wallet does.

All the more reason to invest in one that’s perfectly functional. It should be a pleasure to look at, hold, and use.

You have to consider your everyday needs: Do you have a lot of cards? Do you need to hold lots of cash? Buy something that makes sense for you.

Clean out your current wallet before buying a new one. Of the stuff you carry in your wallet, 75% probably isn’t necessary.

Five Things Men Should Splurge On (That Most People Tell You To Buy Cheap)

My Advice: Go for a slim card holder with an optional slot or clip for bills. If you need more room, choose a slim bifold card holder (that also carries cash).

A Versatile, Refined Belt

Think of how much you beat up your belts with each wear. They’re pulled back and forth, strained at the fastening point.

Soon enough they get misshapen and discolored.

Wouldn’t it be better to find a belt made from a high-quality, full grain leather?

Cheap leather (sometimes called “genuine leather”) is made from leather scraps that are pressed and bonded together. The result is shiny and looks like junk. These substandard “leather” belts peel, crack, and bubble.

Full grain leather belts last. Unless you like replacing cheap belts every few months, buy a solidly-constructed dress and casual belt.

Five Things Men Should Splurge On (That Most People Tell You To Buy Cheap)

My Advice: Take a look at Anson Belt & Buckle. Anson has a great range of dress and casual belts. Best of all, each one micro adjusts.

This means instead of having five holes spaced out 1″ apart, there’s a track that allows you to have 30+ different sizes, spaced 1/4″ apart. No more being in between belt holes.

The dark brown leather strap with the 1.5″ classic buckle in gunmetal is a great everyday option. For something more formal, I like the 1.25″ black leather strap with traditional buckle in gold.

They also have a gift box option: Choose three buckles and two straps (or three straps and two buckles) for $100.

Build your own here.

Comfortable Dress Socks

For dress socks, you want to buy the good stuff. Go for wool, fine cotton, silk, or cashmere.

As for length, always over the calf. They won’t slip down throughout the day. Because you never want to expose bare skin if your cuff lifts up while sitting down.

Dress socks should be solid colored or decorated with a simple pattern. They should also be thin and elegant, not thick and cushy like your gym socks.

Most mass production socks are machine-finished at the toe. That makes them flat and rough. It can irritate your skin too.

The finest dress socks are hand linked. This process results in a smooth, comfortable finish. Opt for hand linked or smooth finished socks (even if done by machine) when possible.

Five Things Men Should Splurge On (That Most People Tell You To Buy Cheap)

My Advice: Check out the dress socks from Fort Belvedere. Dapper Classics also has a nice selection. For the truly discerning gent, Bresciani is a good choice.

A Tough Everyday Bag

The daily work bag or briefcase endures quite a beating. It’s stuffed with your laptop, papers, pens, your lunch, and whatever your kids may have shoved in there.

If you’ve had yours for a while, it’s probably looking old and raggedy.

Depending on your style, I’d suggest something in tough leather, canvas, or a mix of both.

Five Things Men Should Splurge On (That Most People Tell You To Buy Cheap)

My Advice: I currently use the Filson Original Briefcase and it’s the toughest thing I’ve ever owned. I’m sure I could run it over with a pickup truck and the bag would survive (though my Macbook Air wouldn’t).

If you’re leaning towards leather, a few of my friends love their Jackson Wayne laptop bags. For something more elegant and refined, Maxwell Scott has a nice offering.

Buy Fewer, Better Things

There are plenty of online resources that tell you where to find the cheapest, most affordable versions of men’s clothing and accessories. Others suggest how to get a certain look for less.

I understand the desire to buy affordably. You have to choose your battles when on a limited budget.

But I’ve never been an advocate of going low-budget for everything, no matter what.

Sometimes, it’s important to step your game up, even if it’s one baby step at a time (like buying one great pair of men’s underwear).

Which will you upgrade first?

What’s the first item you plan on upgrading? Let me know in the comments below.

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