Most guys want to dress better but assume it means spending a lot. It doesn’t. Dressing better is really about fit, confidence, and a few smart choices that make your outfits look intentional instead of accidental. And if you’re asking how to dress better without buying a whole new wardrobe, the answer starts here.

This post is built from my conversation with menswear expert Simon Goldman on Episode 106, who broke down style in the simplest way possible.

“It really all comes down to fit.”

So let’s build the version of you who looks put together without overspending.

What’s the fastest way to dress better without spending a lot?

Fit. Always fit.

If your clothes fit well, you already look more put together than guys wearing three-hundred-dollar shirts that don’t sit right on their body.

Simon said it perfectly.

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

You don’t need more clothes.
You need better-fitting clothes.

Here’s your rule:
Try everything on.
Sit. Stand. Walk.
If it pulls, clings, pinches, or makes you adjust it, it’s not helping you.

If you need more confidence-driven thinking, read <u>How Do I Build Confidence If I’ve Never Had It?</u> and <u>How Do I Stop Caring What People Think?</u>.

Shop Smarter, Not More

Most guys buy clothes in reaction to a feeling.
Stress. A breakup. A date. A moment where you want to reinvent yourself immediately.

That is how you end up with random pieces you never touch.

Simon’s advice is simple.

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

Here’s the strategy:

1. Go to a well-curated store like Buck Mason, J.Crew, or Banana Republic.

2. Try on different silhouettes to learn what fits your body.

3. Take note of the sizes and cuts that flatter you.

4. Leave without buying anything.

5. Go find the same fits secondhand or budget-friendly.

This saves money and guarantees you’re buying clothes you’ll actually wear.

For more structure, check out the <u>Lifestyle</u> section.

Build a Simple Formula You Can Repeat

The best-dressed guys aren’t doing fashion experiments every morning. They just have a formula that works.

Simon said something I really relate to.

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

Your formula might look like:

• one pair of dark denim

• one pair of well-fitting trousers

• blank tees in black, white, gray

• simple leather shoes (derbies or loafers)

• an unstructured jacket

• an Oxford button-down

Everything goes with everything.
You never scramble before leaving the house.
You always look intentional.

If you want the mindset version of this, read <u>What To Do When You Feel Stuck</u> or <u>How To Build Momentum When You Feel Lost</u>.

Know Where to Spend and Where to Save

Spend on staples. Save on experiments.
If you’re trying something new, thrift it.
If it’s something you’ll wear often, upgrade slowly.

Simon recommends investing in five pieces:

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

That doesn’t mean spending big.
It means finding quality versions secondhand or from value brands.

The blazer especially should be unstructured because it works everywhere without looking too formal.

Use Secondhand Like a Cheat Code

You can get designer-level quality for a fraction of the price if you know where to look.

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

Platforms to check:

• ebay

• Depop

• Grailed

• The RealReal

• Local thrift stores

• Estate sales

• Flea markets

Search terms to use:

• “unstructured blazer”

• “high-rise trousers”

• “heritage brands”

• “Selvedge denim”

• “vintage leather shoes”

Classic menswear gets listed all the time because its value isn’t fully understood by casual sellers.

This is where you win.

Find Clothes That Feel Like You

The goal is not to dress like TikTok.
The goal is to dress like someone you recognize and respect.

Simon opened up about something real.

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

If it feels forced, uncomfortable, or like a costume, it’s not your style.

Your wardrobe should help you move through your day, not perform through it.

If you want more confidence tied to identity, read <u>What Should I Wear On a First Date</u> or <u>How Do I Build Confidence If I’ve Never Had It?</u>.

Where to Start If You’re Rebuilding Your Style

If your wardrobe is chaotic, start with these five simple upgrades:

1. Replace your worst shirt with a clean blank tee.

2. Find one pair of dark denim that fits correctly.

3. Buy one pair of shoes that aren’t sneakers.

4. Get an unstructured jacket you can throw over anything.

5. Pick trousers you feel comfortable in, not squeezed into.

You’ll look more put together instantly.

Where to Shop When You Don’t Want to Spend a Lot

Entry-Level (great fit, reasonable price):

• Uniqlo

• H&M Premium

• Zara Basics

• J.Crew sale section

Mid-tier but worth it:

• Buck Mason

• Banana Republic

• Everlane

Secondhand power plays:

• Depop

• The RealReal

• ebay

• Vintage stores

Simon’s favorite bang-for-your-buck brand:

“Some of the best bang for your buck is Natalino.”

The Real Secret: Dress Better to Feel Better

Dressing well isn’t about showing off.
It’s about showing up.

It’s about the micro decisions that make your confidence easier to access.
Because when you dress better, you move better.
When you move better, you feel better.
And when you feel better, you’re more yourself.

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

Want to hear the full story? Listen to Episode 106 on Spotify or Apple Podcasts.