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For most of my 20's, I didn't understand the importance of dressing well and presenting myself professionally.

To me, the whole idea of “dressing up” made me feel completely phony and fake – like I wasn't being true to myself.

For the same reasons I hated playing the part of a “salesman” or giving any kind of public presentation, the idea of putting a ton of effort into my physical appearance felt almost repulsive to me.

I used to HATE it when anyone told me to do things like:

  • Wear a suit (for any reason).
  • Polish your shoes and wear dress socks.
  • Put product in your hair so it looks right.
  • Get your shirts and pants tailored.
  • Iron your clothes every day.
  • Wear a tie.

I was NEVER someone who would choose to go through this rigamarole just so I looked right to other people.

In my mind, dressing like a professional was just another way of “selling out” and being someone I wasn't.

The Real Problem With Dressing Sharp

When you boil it all down, the real problem I had with dressing well was that it was unfamiliar territory to me.

Even though plenty of people told me to dress up and put myself together, I'd never been given a proper, sensible (in my mind, anyway), meaningful explanation as to why it mattered, how to do it properly, what kinds of signals I was sending when I chose not to do it.

I kept telling myself it was uncomfortable and it didn't really matter – but all along, I was confusing the uncomfortable with the unfamiliar.

Dressing like a real professional was something I rarely had to think about until I had to start doing job interviews in college. All of a sudden, it started to matter that I didn't dress like I was homeless. At the same time, I felt like a total impostor, dressing up like someone I clearly wasn't.

Wearing a suit and tie wasn't something I wanted to embrace, because it didn't feel natural to me, and I hadn't found any professional-looking attire that actually matched my style.

Unfortunately, I was shooting myself in the foot.

By dismissing the importance of looking sharp and refusing to embrace it, I was sending people all the wrong messages:

  • “This guy is dressing like a kid, not a man… I guess that's how he wants to be treated.”
  • “This guy clearly doesn't care about looking competent and successful, there must be a reason for that.”
  • “This guy obviously doesn't take himself seriously, so why should we take him seriously?”
  • “If this person doesn't pay attention to the details in his appearance, how can we trust him with the details of this job?”

Now, is it judgmental to size someone up based on their physical appearance? In a sense, it is… but that doesn't stop anyone (including you) from doing it.

For the same reason you wouldn't hire a homeless person as your financial advisor or an obese person as your physical trainer, the average person will have no reason to hold you in high esteem if you don't show some care in how you present yourself.

One on hand, it may be judgmental… but on the other hand, isn't it just common sense?

When I Finally Changed

For me, my perspective on this whole issue started to radically change when I discovered a guy named Antonio Centeno on YouTube.

I had never heard anyone explain so eloquently how to dress sharp, why it was important and why it was a lot easier than I realized.

This guy gave me a life-changing education. I really mean that.

Once I started applying the lessons I learned from his videos, everyone I worked with started to notice. Almost overnight, people started treating me with more respect and professionalism, and a lot of positive changes happened in direct proportion to the way I chose to present myself each day.

For all the years I had fought against the idea of “dressing like someone I wasn't”, I was completely missing the point. I had overlooked the multitude of benefits that came with presenting myself like a professional.

For me, the biggest “Aha Moment” was when I heard about the concept of the interchangeable wardrobe from Antonio. I'll let him explain it…

The reason this resonated with me is because it was simple.

I already hated the idea of working hard to look and feel uncomfortable (or so I told myself), but when I heard about the interchangeable wardrobe, it really made sense and it was actually kind of fun!

This was a way I could put just a little bit of effort into the selecting the right clothing items ONCE, so every time I went to my closet in the future, I could pick out ANYTHING and it would always look great.

one week with 13 pieces of clothing

When I finally decided to embrace this idea, a lot of good things started happening in my professional life.

  • I felt more confident
  • I made a killer first impression with new clients and customers
  • I suddenly had instant credibility with the people I met
  • Everyone got the subliminal message that I wasn't just a kid or a loser, I was someone to be taken seriously
  • The people in charge started to see that I was someone who paid attention to the details that others missed

Now, as a man – I'm obviously speaking to the male audience out there, but I'm aware that many of these same challenges also exist for women.

Justine Leconte is a fashion designer and YouTuber with a huge library of similar videos and content that speaks directly to the female audience. For all the ladies out there looking for inspiration and guidance in this department, she is a great resource with paying attention to!

What About the Real Estate Investor?

Now, suppose you're not working in the corporate world. Does this stuff still matter?

Even in the real estate realm, if you're not as a real estate agent, broker, banker or realtor – is it still important to dress the part of a professional?

Perhaps you aren't meeting with prospects in-person every day, and maybe first impressions happen a lot less frequently in your typical day of business.

Heck… maybe you're even one of those “virtual” real estate investors, and most of your deals come together through the internet (where nobody sees your face or how you dress). Does it really matter if you “dress like a professional” in those scenarios?

Personally, I don't think this is ever an issue you can completely ignore just because you work from home or behind the veil of a computer.

Even if most of your business happens from your office – you will still have the occasion to do things like:

  • Visit a title company
  • Meet with a lender
  • Go to a networking event
  • Sit across the table from a buyer or seller, etc.

At some point, we all have to be conscious of the fact that our physical appearance matters.

We need to be ready to dress the part when the time calls for it (even if those times are few and far between).

How I Dress As A Real Estate Investor

Back when I was working an 8-5 job in the banking industry, it was important to dress sharp.

But now that my working life has changed drastically and I work from home all day, does it honestly matter if I wear anything other than sweatpants to work? Does it matter if I wear pants at all?? Sorry… TMI, I know.

Don't get me wrong – ever since my working situation changed forever, I have NOT been putting on a tailored suit before going to work each day.

But at the same time, I still pay attention to what I'm wearing.

Why? Because it is very common for me to do things like:

  • Unplanned video calls with buyers, sellers, customers and business partners via Zoom or Skype
  • Sending video emails to buyers, sellers, banks, title companies, prospects, etc.
  • Recording explainer videos for the REtipster YouTube Channel
  • Various in-person lunches, breakfasts and coffee meetings with people in my local market

Even though I definitely dress in a way that's very casual and comfortable, I'm still putting thought into it, and I'm proudly presentable to anyone, at any time, regardless of who I might bump into (whether it's online or in-person).

As a bare minimum, this is what I would recommend to other real estate investors as well.

You don't have to go crazy with it, but don't let yourself fall into “slob” territory either.

Where I Get Clothes

When I finally started paying attention to the way I dressed, one of the big obstacles I had to overcome was figuring out what my “style” was going to be, and where/how to get clothes that fill out this interchangeable wardrobe of mine (all while staying within a reasonable budget).

To this day, I still have NO idea how to shop for clothes.

If you drop me off in the middle of Kohl's or Macy's and tell me to pick out a few outfits, I'll probably screw it up.

I'm terrible at finding outfits that look good and pair with one another.

However, if a professional stylist shows me a full outfit, it's easy for me to say whether I like it.

Luckily, I learned about a company called Stitch Fix, and this service has single-handedly solved almost all of my clothing problems.

How it works:

stitch fixStitch Fix is an online styling service that delivers a personalized shopping experience (it's for men, women and even children).

After you fill out your Style Profile, a Personal Stylist will handpick pieces to fit your tastes, needs, and budget—and mail them right to your door.

Each box comes with a curated selection of clothing, shoes, and accessories for you to try on at home. Simply keep the items you like and send back the rest in a prepaid USPS envelope. Shipping and returns are always free.

Other than the price you pay for these items, there are no hidden costs or fees for working with them (the one caveat is that you do need to keep at least one of the five items they send you with each box – otherwise, you'll have to pay $20 to cover the styling fee for that shipment).

Ultimately, StitchFix makes their money by charging you full retail prices for the items you decide to keep, there's no such thing as getting items “on sale” through this service.

For someone like me (who will probably buy the wrong things on my own anyway), this kind of convenience and eye for style is absolutely worth the price.

After using StitchFix for a couple of years, 80% of the clothes in my closet have come through this company – and consequentially, I actually wear all of the clothes I own. None of my clothing budget is wasted because all of the things I buy are things I love to wear.

So… if you're anything like me when it comes to style and shopping (you know who you are), Stitch Fix is currently the best resource I know about. If you want to give them a try, you can get a $25 discount on your first order if you go through this referral link.

Get Started with Stitch Fix!

Why Dressing the Part Matters

Regardless of your profession, your style or where you get your clothes – there's one key takeaway I want you to walk away with here.

This isn't about trying to meet the standards of others or be someone you're not.

Presenting yourself well (whether it's the way you dress, the way you carry yourself, the way you take care of your body or the way you speak to others) is all about putting your best foot forward, having self-respect and being ready for any situation that life throws your way.

If a situation calls for you to look and act the part of a true professional, you should aspire to put yourself forward in a way that makes people proud (not embarrassed) to be associated with you.

When you have the confidence to rise to the occasion, presenting yourself well and making a great first impression (whenever and wherever the situation calls for it) can open a lot of doors, simply by dressing the part.

It's not that you have to become obsessed with your physical appearance. On the contrary – with a service like Stitch Fix, you can let someone else do the obsessing for you, and they'll get paid accordingly when they make you look great.

About the author

Seth Williams is the Founder of - an online community that offers real-world guidance for real estate investors.

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