5 Key Pieces Of Advice If You Want To Learn How To Dress Better

by Barron Cuadro  |  in Style Tips

Overhauling your look can be intimidating and if you’re new to the fashion game, it can be incredibly overwhelming, but it’s not impossible! With a few nuggets of advice, you can make dressing better much easier.

I got together with a few of my menswear YouTuber friends and sat down in front of the camera (after a few beers) to dispense some of our best advice for guys trying to dress better.

Luckily, we all live on different sides of the men’s fashion spectrum so you’re bound to find a piece of advice that will stick with you. 

Have you seen the video?

If not, check it out below:

5 Quick Tips For Dressing Better

Here are some tips from me and some of my stylish menswear friends. 

Solid Colors FTW 

I modeled for a little bit in my early 20s and the main thing they teach you is to wear solid colors.

Nick English


If you’re looking for tips on how to dress better, this is a solid one to start with. Simply wear solid colors. It takes the uncertainty out of your outfit-building process because you won’t have to worry about different patterns working together.

Here’s an article you may enjoy if you’re looking for easy outfit color combos for guys.

I’d take it one step further towards simplification. Memorize your menswear neutrals (tip 2 here), and make sure your basics and essentials are in these menswear neutral colors.

You’ve Gotta Feel Comfortable

The number one thing is that you must feel comfortable in what you’re wearing! If you don’t feel comfortable, everyone else is going to see it.

Sure, this is easier said than done, especially in the beginning when you’re trying to improve your style and dress better. But if you’re instantly uncomfortable in a brand new look or outfit, maybe you’re taking it too far, too quickly!

Start with one new thing first: maybe a new shirt style, or a different pant silhouette, or a mid-layer that you’re not used to.

Get used to that one thing, keeping everything else the same. The more you wear that newly-acquired piece, the sooner you’ll get used to it, and it’ll just feel normal to you. This will help you build the confidence to try more new things.

Fit Is King 

This is an easy one: Start wearing clothes that actually fit your body.

Brock McGoff

The Modest Man

Fit makes the biggest difference in your style! If you’re wearing stuff that isn’t flattering, your outfit won’t look good, no matter how expensive that garment may be.

It’s important to figure out how clothes should fit your body first. What flatters you? What makes you look slimmer / taller / wider / more muscular… whatever you’re trying to achieve?

For example, I know that if I wear pants labeled “slim” or “skinny”, they don’t fit my huge legs, so I often go with an athletic or a straight leg. These silhouettes actually fit me well and still look slim, even though they’re not labeled that way.

Try lots of sizes and cuts, and you’ll learn what looks best on you.

Know These Two Things 

Two things: Know your body type and know your skin tone colors.

Gabe Dechter

The Mensch

This builds on the tips that came before it. When you understand your body type, it’s easier to find clothing that fits you well and flatters you.

Everyone’s body is different, and you get to know yours intimately when trying on a bunch of clothing.

It’s not easy, and it takes a bunch of time, and it’s tiring. It’s not always fun, either. But if you do it once, assuming you more or less stay the same size, it makes the job so much easier the next time around.

Same thing goes for your skin tone. You have to try on different colors to figure out what looks best on you. We have a few posts on colors and skin tone, but if you’re not ready for that yet, as long as you’re wearing menswear neturals, you’re fine.

Learn The Rules, Then Break Them

It’s important to understand and learn the rules + guidelines of what dressing well means, but anyone can follow their own rules once they know the basics.

Barron Cuadro

Effortless Gent

This is the best part. Once you’ve mastered the rules of dressing well, you can decide which rules to follow and which ones to break.

Great style and having any sort of fashion sense comes from knowing the rules and breaking them to display a style all your own.

If you want to try new trends, we have a few tips for you, so give those a shot when you’re ready. And I also but together a video about why lots of men’s fashion advice is wrong, and some style truths no one is telling you.

Want to hear more?

Make sure to check out the video at the top of this post to hear the full conversation.

What other style questions do you have? Feel free to hit me up on Facebook and Instagram!