How to Start Dressing Intentionally

Author: Robbie Lannon

Posted on: Aug 06, 2025

There’s a saying that human beings form first impressions within the first seven seconds of meeting someone. You’ll subconsciously decide if another person is worth your time, sometimes before they ever open their mouth. The way you dress can make or break those first few seconds, so why not make the most of them? Tell the person you’re meeting exactly who you are, who you see yourself as, without saying a word.
Please take note of the language I’m using here. This site is meant for all sorts of personal styles. Mine tends to lean preppy and boring. That doesn’t mean my style is the right way to dress. It works for me, as an office-working dad of two. I, for better or worse, look like the classic “American Dream” sort of dad. The guy you see at the grocery store and think, “Yep, he’s got a corporate job and a house and a wife and 2.3 kids and a dog.” And that’s perfect for me!
But, if you put my brother in my wardrobe, it would look like a costume. He’s a shop manager at a large construction company, runs a landscaping business on the side, and has a hobby farm where he and his wife board horses (yeah, I know, he’s pretty awesome!). He wears more jeans and company-branded t-shirts than I do. And he should. His story is very different from mine, and we shouldn’t dress the same.
Now that I’ve gotten my rambling out of the way, how does someone go about dressing intentionally?
It all starts with the story you want to tell.
Here’s a fun test for you:
Picture a lumberjack. Now an auto mechanic. Now an investment banker. Now a software developer.

Each of those people probably looked very different in your mind. The lumberjack likely wore a red and black plaid flannel shirt with suspenders and jeans. The mechanic was in a denim jumpsuit. The investment banker had on a gray or navy suit with a tie. The software developer? Hoodie and sweats.
That’s the power of perception. So take advantage of it.

Telling your story doesn’t mean wearing whatever everyone else is wearing. It also doesn’t mean going so far out of your comfort zone that you feel like you’re wearing a costume.
What it does mean is finding a style that fits both your lifestyle and your aspirations, and learning how to adjust that style for the situation.
Take my shirt collection, for example. I’ve got four different Oxford Cloth Button Down (OCBD) shirts in various colors and patterns. By dressing intentionally for the situation, I can wear them casually with jeans and white sneakers for a coffee run or trip to the farmer’s market, or dress them up with chinos or dress pants, an odd jacket, and a tie for the higher end of business casual. Both ends of that spectrum still fit the story I want to tell without me ever having to say a word.
NAIL YOUR FIT

Fit is always the most important part of style. The fabric doesn’t matter if your jeans are pooling around your shoes. Functionality means nothing if your t-shirt is two sizes too small. Nail your fit, and everything else is gravy.
So where should you start? Wherever you're comfortable. Most guys have a size they think works for them. The best advice I can give: start there, then adjust a little in either direction until you feel like you look your best.
Something I picked up along the way: try sizing down.
Most guys wear a size too big. I was one of them. At 5'8", I used to wear large t-shirts. I thought that was the right size because they felt like I was “wearing nothing at all.” Then I saw pictures of myself and realized I was swimming in them. I dropped to a medium. Still had room to play with. Tried a small in a few brands, and suddenly all my clothes actually fit.
My mindset had to shift. I let go of the “I’ve always been this size” mentality and started buying what actually fit.
Sizing down will feel off at first. Ask yourself, is this uncomfortable or just unfamiliar? Most of the time, it’s the latter. But if it’s actually too small, you’ll know right away.
Of course, all of this only matters if you’re aiming for a timeless fit. Something that would’ve looked good on James Dean or Cary Grant in the 1950s and still looks good today on David Beckham or Ryan Gosling. These fits aren’t too tight, too loose, too trendy, or too retro. They’re classic. They don’t draw attention, but they do look right.
Want to go deeper down this rabbit hole? Don’t reinvent the wheel. Take a look at Primer Magazine’s Principles of Fit series or Real Men Real Style’s Style Pyramid if you want to see a visual on how these fits look. These are great creators that are going to come at things a little differently than I will, but we tend to say similar things. I cannot recommend them highly enough!

FIND THE GOLDILOCKS OUTFIT
Easier said than done, but it gets easier the more you do it.
There are obvious examples. A three-piece business suit makes you look ridiculous at the beach. Swim trunks and sandals won’t work in a boardroom.
What you’re aiming for is to understand what’s expected in a setting, then take one small, thoughtful step beyond it.
This could mean:
A sport coat or a tie in a business casual office (not both, unless a tie is expected),
Swapping a t-shirt for a fitted polo in a jeans-and-tee setting,
Upgrading shoes: penny loafers instead of sneakers, monk straps instead of penny loafers, boat shoes instead of sandals.
It doesn’t have to be drastic. Just enough to show you gave it some thought.
My favorite quote on this is from Hardy Aimes:
“A man should look as if he had bought his clothes with intelligence, put them on with care, and then forgotten all about them.”

This takes practice. One thing I do is wear a new outfit at home for a day or two before taking it out in public. Be prepared for weird looks from roommates, significant others, or friends who drop by. I’ve definitely gotten those.
Case in point: I used to hate the idea of wearing a t-shirt with a suit. But then I got invited to a very casual wedding reception where “golf attire” was acceptable. Weddings are one of the few events I take seriously when it comes to dressing. I usually aim for at least a jacket, preferably a full suit.
I had picked up a linen suit earlier in the year during a summer sale, and thought, okay, let’s try the t-shirt look. I tested it out at home a few days before the event, which happened to be the afternoon friends came over to play Magic: The Gathering. So yes, I was that guy—playing cards in a suit, on a Wednesday afternoon.
But it worked. I got comfortable in the outfit. I showed up to the reception looking sharp. I wasn’t outshining the groom, but I was definitely one of the better-dressed guys there. All because I took a little time to test it out and feel natural in something new.
So there you have it. A few simple ways to get started dressing more intentionally. Send me a message and tell me your story!

Tags: style, fundamentals