Most guys do not need a bigger wardrobe.

They need a better one.

That is the difference.

A lot of guys have closets full of random clothes they barely wear. Old hoodies from college. Shirts bought for one specific event. Jeans that fit differently every time you put them on. Sneakers that only work with one outfit.

And then every morning somehow still feels difficult.

You stand there thinking:
“What am I even supposed to wear?”

The problem usually is not that you need more clothes.

It is that you do not have enough reliable pieces that actually work together.

Menswear creator Simon Goldman talked about this during his Guyset interview when he explained how style becomes easier once you start building around foundational pieces instead of chasing trends.

That shift changes everything.

Because good style is usually not about constantly reinventing yourself.

It is about creating a wardrobe where almost everything works together.

Dark Wash Jeans

If there is one item almost every guy should own, it is a good pair of dark wash jeans.

They work nearly everywhere.

You can wear them on dates, to dinner, to work in casual offices, while traveling, or just walking around the city on a normal day.

The reason dark denim matters so much is because it sits perfectly between casual and elevated.

It feels intentional without trying too hard.

And honestly, the fit matters far more than the brand.

Simon said something during the episode that applies to almost every outfit a guy wears:

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

That is completely true.

Jeans that are too skinny can throw off your proportions. Jeans that are too oversized can make you look uncomfortable if the silhouette is not balanced correctly.

A well-fitting pair of dark jeans instantly makes jackets look cleaner, shoes look better, and simple outfits feel more intentional.

Even Esquire Men’s Fashion Advice constantly emphasizes that fit matters more than expensive labels.

Plain White and Black T-Shirts

There is a reason almost every stylish guy owns simple T-shirts.

They work with everything.

Jeans.
Trousers.
Jackets.
Overshirts.
Sweaters.

The point of a great T-shirt is versatility.

Simon talked about how most of his wardrobe is built around simple blank tees because they allow the rest of the outfit to work naturally.

And honestly, this is where a lot of guys overcomplicate style.

They think dressing better means louder outfits or trendier pieces when most good style actually comes from simplicity and consistency.

That is why How Do You Dress Better As a Guy? is less about trends and more about understanding fit, confidence, and proportions.

Even GQ Style Guides constantly returns to the same idea: foundational basics matter more than constantly chasing trends.

An Oxford Shirt

Every guy eventually needs something slightly more elevated than a T-shirt.

That is where the Oxford shirt comes in.

It is probably the most versatile shirt a guy can own because it works almost everywhere: first dates, dinners, work, family events, nights out, and casual weekends.

You can wear it buttoned up, layered over a tee, tucked into trousers, or open with jeans.

Simon literally called it “the most versatile shirt ever made.”

And he is probably right.

A white Oxford and a light blue Oxford cover almost everything most guys need.

Clean Shoes That Feel Intentional

A lot of guys underestimate how much shoes change an outfit.

You do not need designer shoes.

You just need shoes that look intentional.

Dirty running sneakers instantly make an outfit feel sloppy. Clean sneakers, loafers, leather shoes, or boots completely change the energy of even the simplest outfit.

Simon specifically talked about leather derbies and loafers because they work across both casual and elevated situations.

Shoes are one of the fastest ways to make outfits feel more mature without looking overdressed.

A Jacket That Pulls Everything Together

Most good outfits have a strong layer.

That layer could be a denim jacket, chore coat, bomber, suede jacket, or lightweight wool jacket.

The specific jacket matters less than the feeling it creates.

Jackets give outfits shape and personality.

Simon talked during the episode about how even simple jackets can completely change the feel of an outfit when the fit is right.

And honestly, jackets often become the piece people associate with your style the most.

Trousers That Actually Fit

A lot of guys only wear jeans because they think trousers automatically look too formal.

That is not true anymore.

Modern trousers can look relaxed, clean, and incredibly versatile when styled correctly.

Good trousers instantly make outfits feel sharper, calmer, more adult, and more intentional.

And contrary to what most guys think, they are often more comfortable than stiff denim.

Once you find a pair that fits properly, they become one of the easiest things to build outfits around.

A Sweater You Actually Feel Good Wearing

This sounds small until you own one.

A good sweater solves half your wardrobe problems during colder months.

You can throw one over jeans, trousers, or a button-down and instantly look more put together without feeling overdressed.

Texture matters a lot here too.

Simon talked about how textures like wool, corduroy, cable knits, and heavier fabrics make outfits feel more visually interesting without needing louder colors or complicated styling.

That is why simple outfits can still feel stylish.

Most Guys Need Less Than They Think

This is probably the biggest mindset shift.

Good style usually comes from repeating strong basics well.

Not from constantly buying new clothes.

The best-dressed guys are usually not reinventing themselves every day.

They just know what fits them, what colors work for them, what outfits make them feel confident, and what pieces consistently work together.

That simplicity is what makes style feel effortless.

And honestly, confidence is usually what people respond to most anyway.

Not whether your sweater is trendy.

That is also why so much of personal style overlaps with confidence and identity in your 20s. I talked more about that in How To Act Confident When You Don’t Feel It, because most style advice is really confidence advice underneath it.

And honestly, personal style usually develops slower than people think. Most guys do not suddenly “figure it out” overnight. It comes from experimenting, paying attention, and slowly learning what genuinely feels comfortable, which is something I explored more deeply in How Do You Find Your Personal Style as a Guy?

FAQ

What clothes should every guy own?

Every guy should own dark wash jeans, plain white and black T-shirts, an Oxford shirt, versatile shoes, a good jacket, trousers that fit correctly, and at least one sweater that layers easily.

What colors should guys buy first?

Neutral colors like black, white, navy, gray, olive, brown, and dark denim are easiest to style because almost everything works together naturally.

Do guys need expensive clothes to dress well?

No. Fit matters far more than price. A simple outfit that fits correctly will almost always look better than expensive clothes that fit poorly.

What shoes should every guy own?

A clean pair of sneakers, versatile loafers or leather shoes, and simple boots will usually cover almost every situation.

How do guys build a better wardrobe?

Start with foundational pieces instead of trends. Focus on clothes that can work together easily and that genuinely fit your lifestyle.