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How to Upgrade Your Wardrobe and Dress Better (Ep. 128)

Antonio CentenoWhen I was doing my big corporate internship after my sophomore year of college, there was one thing I noticed all the time about my co-workers.

Even though they were technically wearing “business casual”, they weren’t dressing well. 

My office was a sea of ill-fitting slacks, lazily tucked-in shirts, and brown Sketchers that only barely passed for business casual. Most people were simply dressed to meet the office criteria – nothing more.

Of course, I wasn’t much better. While I did pay a bit more attention to how my shirts fit, my attitude about how I dressed mainly boiled down to:

“Who cares how I dress? All that matters is how well I do my work.”

This attitude was partly forged through my interactions with people in startup culture. I loved the idea of being a Mark Zuckerberg type – I wanted to build a career for myself that would allow me to wear a hoodie and jeans if that’s what my whim called for.

Recently, though, I’ve realized that what I’d once thought of as an expression of freedom from “restrictive” dress codes was, at least partly, also an expression of my own laziness. I didn’t want to dress well because I didn’t know how to dress well.

Additionally, I’ve come to realized a couple of other things about dressing well. First, the way that you dress forms a large part of the impression you make on other people. If you want to take advantage of the Halo Effect, dressing well is one of the best ways to do it.

Secondly, the way you dress affects your mindset. 

Since I work mainly from home and don’t have a boss, I can wear whatever I want. I could be writing this very sentence while dressed as Tingle from Majora’s Mask for all you know. However, I noticed a while ago that I felt more motivated to work on the days when I took the time and effort to dress somewhat professionally.

As a result, I usually put on a button-down shirt, nice jeans, and my dress boots each day after I finish my morning routine. By doing so, I feel like I’m stepping into the role of a professional – and my work output is definitely influenced by that.

All this is to say that I think you should start thinking more deliberately about how you dress (at least if you were as nonchalant about it in the past as I was).

But how do you go about doing that?

I’d be willing to bet that the majority of you are just like me – you walk into a clothing store and immediately get overwhelmed by all the choices. With all the different garments, fabrics, colors, and combinations, it can be hard to know where to start – especially when you’re trying to assemble a wardrobe that can handle many different levels of formality.

This week’s episode should help you to start building a foundation of knowledge for doing just that. My guest on today’s episode is my friend Antonio Centeno, the founder of Real Men, Real Style.

Antonio is an absolute expert on men’s fashion; his site has over 1,000 articles on dressing and grooming, and his YouTube channel has over 700,000 subscribers. He also knows enough about women’s fashion to help girls start to build a foundation, which means this episode isn’t just for guys.

In this episode, you’ll learn some basic and not-so-basic things; how to start building a versatile wardrobe, what kind of shoes to buy for an interview, the function of a pocket square, and more. Enjoy!

Lastly, here’s a picture of the shirt I was wearing during this interview – Antonio and I talk about it, so I wanted you to be able to see it (it’s from Express if you’re curious):

Checkered Shirt

Things mentioned in this episode:

Want more cool stuff? You can find all sorts of great tools at my Resources page.

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How to Upgrade Your Wardrobe and Dress Better