How To Dress Better Without Spending a Lot (A Simple Guy’s Guide)

Most guys think dressing better requires money. A new wardrobe. A full reset. A version of themselves they can’t afford yet.

It doesn’t.

Dressing better is rarely about price. It’s about fit, intention, and learning how to make a few smart choices that change how you show up. The goal isn’t to look rich or trendy. It’s to look like you know who you are.

That idea came up again and again when I sat down with Simon Goldman on Episode 106. And he summed it up in the simplest way possible.

“It really all comes down to fit.”

Once you understand that, everything else gets easier.

Fit Is the Shortcut Everyone Ignores

If your clothes fit, you already look more put together than most guys.

It doesn’t matter if someone is wearing a three-hundred-dollar shirt if it pulls at the shoulders, bunches at the waist, or makes them adjust it every five minutes. Poor fit breaks the illusion immediately.

Simon put it plainly.

“If your pants don’t fit well, the whole outfit will feel off.”

That’s the baseline. Before color. Before brand. Before style. If something pinches, clings, rides up, or makes you self-conscious, it’s not helping you.

This idea is backed up by research on enclothed cognition, which shows that how clothing fits and feels directly affects confidence and behavior, as explained by Psychology Today.

The best rule is simple. Try everything on. Sit down. Stand up. Walk around. If you forget about the clothes once they’re on, you’re doing it right.

Why Most Guys End Up With a Closet Full of Nothing

A lot of guys shop emotionally.

A breakup. A date coming up. A moment where they feel behind and want to reinvent themselves immediately. That’s how you end up with random pieces that don’t work together and never leave the hanger.

Simon’s advice cuts straight through that pattern.

“Just be a little bit more scrappy. Go to flea markets, go to thrift stores, go to consignment shops.”

But before that, there’s a smarter move most guys skip.

Go to a well-curated store. Try on different silhouettes. Learn what fits your body. Take mental notes. Then leave without buying anything.

Once you know what works, you can find those same pieces secondhand on platforms like Grailed, The RealReal, or eBay, often for a fraction of the price.

That’s how you shop with intention instead of impulse.

If your style anxiety ties into confidence more broadly, How to Act More Confident When You Don’t Feel It Yet connects directly here.

The Power of a Simple Formula

The best-dressed guys aren’t experimenting every morning. They’ve built a formula they trust.

Simon said something that stuck with me.

“I stick to what I know works for me and feels comfortable for me.”

That’s the real style cheat code.

A few dependable pieces. Neutral colors. Everything works together. You don’t overthink it. You don’t scramble before leaving the house. You just get dressed.

For most guys, that looks like dark denim, a solid tee, simple leather shoes, a button-down, and one jacket that elevates everything. Nothing flashy. Nothing forced. Just intentional.

If you’re rebuilding from scratch, What Should I Wear On a First Date is a good place to start.

Spend Where It Matters, Save Where It Doesn’t

Not every piece deserves the same investment.

Spend on the things you wear constantly. Save on experiments. If you’re trying something new, thrift it. If it becomes a staple, upgrade later.

Simon laid out five pieces worth prioritizing.

“A good lace-up pair of derbies… a nice pair of slacks… dark wash denim… blank tees… an unstructured blazer.”

None of that requires breaking the bank. Especially if you’re buying secondhand or off-season.

Secondhand Is the Real Advantage

Secondhand shopping is where style becomes accessible.

“You can find some really fantastic deals on those platforms.”

Sites like Grailed, Depop, and The RealReal are full of menswear that was built to last. The trick is searching for classic pieces instead of trends. Heritage brands. Clean silhouettes. Real materials.

A lot of people don’t know what they’re selling. That’s where you win.

Style Should Feel Like You

The goal isn’t to dress like TikTok. Or copy someone else’s aesthetic. Or turn your wardrobe into a costume.

Simon said something that cuts to the heart of it.

“Finding things that feel very me has definitely made me feel more confident.”

That’s the point.

When something feels forced, you move differently. You fidget. You second-guess. When something feels like you, you relax. You stand taller. You act like yourself.

Clothes don’t create confidence. They remove friction from it.

If confidence is the deeper goal, When Feeling Stuck Starts to Mess With Your Confidence ties everything together.

Where to Start If Your Style Is a Mess

If your wardrobe feels chaotic, don’t overhaul it. Replace one bad piece at a time.

Swap out your worst shirt for a clean tee that fits.
Find one pair of dark jeans that sit right.
Buy shoes that aren’t sneakers.
Add one jacket you can throw over anything.

You don’t need more clothes.
You need fewer, better ones.

The Real Reason Dressing Better Works

Dressing well isn’t about impressing people. It’s about making confidence easier to access.

When you dress better, you move better.
When you move better, you feel better.
And when you feel better, you show up more fully as yourself.

You don’t need a new wardrobe.
You need better choices.

And once you make them, everything else starts to feel lighter.

FAQ: Dressing Better Without Spending a Lot

Do I need expensive brands to look well dressed?
No. Fit matters more than brand. Well-fitting clothes from affordable or secondhand stores will always look better than expensive clothes that don’t sit right on your body.

What’s the first clothing upgrade every guy should make?
Start with fit. Replace the item in your closet that fits the worst. One good-fitting pair of jeans or one clean tee can instantly improve how put together you look.

How many outfits should a guy actually own?
Fewer than you think. A small rotation of neutral, well-fitting pieces that all work together beats a closet full of random items.

Is thrifting really worth it for men’s clothing?
Yes. Men’s classic pieces are often underpriced secondhand. If you know your size and what fits you, thrift and resale platforms are one of the best ways to upgrade your wardrobe cheaply.

Why does dressing better improve confidence so quickly?
Because it removes friction. When your clothes fit and feel like you, you stop thinking about how you look and start focusing on how you move through the world.