How to Dress in 2026: The Art of Leveling Up

How to Dress in 2026: The Art of Leveling Up

I have been working this for a couple years now and it sort of just felt like 2026 was the time to publish it. All I can say is it is from a place of love and care...and desire to help many others...and I hope will help you!

To go back for a second...I can still remember March 2020, and COVID had just set down on Charlotte. We were exactly one week away from opening our brand new storefront...an endeavor plagued by delay after delay, and our first store build from the ground up.

With our grand opening shuttered due to stay-at-home notices, the world shifted overnight. We entered a casual era where people could...and had to...work from home. I remember thinking at the time...I don’t know if it will ever go back to the pre-COVID days of people dressing up for work.

And for years...it didn’t.

Aside from the guys boasting that they no longer had “dress up”...eye roll...and the obvious drop in business from our pre-COVID regulars, I noticed one fascinating constant.

The people I viewed as successful...those in roles of authority and power, my “high agency” clients...didn’t miss a beat. They kept dressing the part. They saw the sudden low-hanging fruit before anyone else did. While the self-conscious were happy to ignore a part of their life they never felt comfortable with, the confident started getting that much further ahead.

They realized that dressing one level up in any situation is a cheat code. It provides you with control of your surroundings.

Today, slowly but surely, the tide is sliding back. The trend is moving toward the realization that a little extra effort goes a long way. Dressing the part is a great equalizer in life and careers...much like eating healthy or exercising.

So, as I sit here at the start of 2026, I am announcing to all those in denial: It’s time. The adage of “dress for the job you want” has never been truer....but now...you can lead the pack...it is your cheat code to get ahead.

Look...I get the anxiety that comes with getting dressed. I’ve mentioned numerous times that I was once a “finance bro” with no clue how to dress. It was easy to ignore...I’d just look at the people next to me, follow their lead, and assume I couldn’t go wrong. But blending in and settling into a mid-level career as a “Steady Eddy” was never on my bingo card. I needed to suck it up and be better.

For those wanting to make a change and be better in 2026, this is your guide. It is simple...but simple does not necessarily mean easy.

Step 1: Start With What You Have

I advise all OMJ clients that the first step is not getting rid of everything you own. That is extreme...it’s like going from your couch to a marathon. The fastest way to fall back on bad habits is to get overwhelmed and give up. Perhaps other clothiers would tell you to start over...but I believe that is too overwhelming...you likely have a good base...let’s celebrate that!

Instead, audit your closet:

• Keep: Things that fit well and you feel good in.

• Alter: If you have high-quality items that just don’t sit right, see if a tailor can save them.

• Donate: If you don’t know how to wear it, or if you default to never wearing it because it doesn’t match your personality...let it go.

Step 2: Build Your “Core”

Once you’ve cleared the clutter, it’s time to get pieces that fit your actual life. If you are soft-spoken and quiet...let’s stay away from loud patterns.

I recommend a handful of super-versatile pieces. With these, you can wear anything with anything, and it requires zero thinking in the morning:

• 1 Navy Suit

• 2 Sport Coats

• 2 Trousers (Blue and Grey)

• A few White and Light Blue shirts

• 1 pair of Dark Brown shoes

This is a minimal investment that establishes your core identity. Once you have the basics, you can layer in “level up” pieces later...like that interesting plaid sport coat. But remember: You don’t want to be the guy who wears the same crazy, noticeable jacket to every event. It loses its cachet immediately. Start with the weekly warriors, and wait on the monthly statement pieces. Also a side note: out of everything I have...I get the most compliments on my navy suit...having a staple piece that fits YOU will ALWAYS turn heads.

Step 3: Become a Student of the Game

I am a “rabbit hole” guy, so I deep dive into everything. You don’t need to do that, but a simple understanding of style helps in two ways:

1. It reduces intimidation.

2. It makes you a subtle expert.

There are few things more empowering than becoming the person at your office that others go to for advice. That is “rare air” on the respect barometer. I have seen it time and time again with our clients...the confidence it brings straps a rocket to the back of their proverbial career. A buddy of mine went from average joe to office style guru...and it changed his career...he is far more successful than most of my friend group today!

You don’t need to be a snob. Just gain some basic knowledge and adopt a helpful, non-judgmental mindset. I

Step 4: Consistency Wins

Take the extra five minutes to dress with purpose. Lay your outfit out the night before... or put on the jacket.

We are all busy, but showing up each day looking your best is what it’s all about. If you do it consistently, you will beat 95% of everyone else.

Early in my finance days, I got some great advice from my manager (shout out Jim Vilsack) I started wearing dress pants instead of the basic cotton chino or golf pant. It was hard not to reach for the polo, but I was always happier when I took the extra time. My career flourished for it. I became someone management knew could be taken to meetings with senior leadership...partially for what I knew, but mostly because I was ready to go.

Golf pants would have kept me on the sidelines.

The Golden Rule: One Level Up