It’s easy to look good, but the real challenge is feeling like yourself, fitting in, and still getting out the door on time. This approach will help make that much simpler.
This isn’t just about "fashion." It’s about confidently presenting yourself in a way that feels natural and thoughtful. Your personal style is a reflection of who you are and how you interact with the world around you.
I often talk about "dressing intentionally" because it’s more than just putting on clothes. It’s about how you carry yourself, how you choose to show up, and what matters to you. It gets right to the heart of what personal style truly means.
For many, this idea might not be new. You probably already care about what you wear and have moved past the stress of getting dressed to instead choosing outfits with a clear purpose. But, just like with anything we do regularly, it’s easy to lose sight of the "why" or get stuck doing things on autopilot without even noticing.
Think about how we all follow unwritten rules: how to shake hands, pausing before we interrupt, or putting our phones away when we’re with people. We weren’t explicitly taught these things, but we’ve learned what’s generally considered appropriate.
Your style works the same way. It’s another layer of understanding how to navigate social situations. Whether you’re heading to an important meeting or just grabbing coffee with someone you’re interested in, what you wear says something about you. The question is, are you consciously choosing and owning that message, or just hoping your outfit will fly under the radar?
Looking good and feeling like yourself shouldn’t be opposing goals. Yet, it often feels like you have to pick between looking polished and being comfortable, expressing your personality and fitting in, or putting in effort and wanting ease.
The truth is, it’s more complicated than that. You’re constantly balancing different things: what you’re doing, how you want others to see you, and how you want to feel both physically and mentally. That’s precisely what dressing intentionally offers. It’s not about finding one perfect look, but rather a way to handle these conflicting factors in the moment.
This guide will show you a simple system I use every day to achieve this. It’s not about overthinking your clothes, but about actually taking a moment to think about them at all.
First, think about where you’re going.
The first step to dressing with purpose is understanding the situation. Many of your clothing choices will depend on practical details.
For example:
- Eating outdoors at a restaurant? You’ll probably want a light jacket and sunglasses.
- Attending a business event? You might need a blazer, or maybe something more relaxed if it’s a younger crowd or specific industry.
- Going to a cold movie theater before dinner? You’ll likely want layers.
My point isn’t just about the temperature; it’s about the whole situation.
Sometimes, the context isn’t so clear-cut. You might be in an environment that has multiple vibes at once, like a business event that’s also on a rooftop bar and feels a bit casual, or a family gathering with both new in-laws and old friends.
What one person considers "underdressed," another might see as "relatable." The goal isn’t to get it absolutely perfect, but to make an educated guess about the overall tone and then dress in a way that makes you feel confident navigating that setting.
Once you grasp the context, it becomes easier to ask yourself the next question: What kind of impression do you want to make there?
Next, consider how you want to be seen.
Your personal style is essentially visual communication. It’s as much about social interaction as it is about expressing who you are.
Do you want to come across as relaxed and creative? Sophisticated and elegant? Carefree and bohemian? Tough and practical? Playful and attractive?
The image you want to project can change, not just based on your personality or usual style, but also depending on where you’re going and who you’ll be with. I have different sides to my own personal style, and I choose which one to highlight based on the situation.
For instance, I wouldn’t wear a flowy, open shirt with a necklace when visiting my fiancée’s parents. And I wouldn’t wear a tech polo to a summer birthday party at a poolside bar in Los Angeles. But I’d happily wear both of those outfits in different, appropriate settings.
It’s really freeing to realize that even if you have a consistent overall style, you can still choose how you want to be perceived based on your destination. This freedom actually encourages you to wear what you feel like, rather than limiting your options.
Then, think about how dressed up you want to be.
You’ve considered where you’re going, what you’ll be doing, and how you want to be perceived. Now, within that overall situation, you get to choose exactly how formal or informal you want your outfit to be.
The event or setting sets the general range, and you pick your specific spot within it. It’s a small decision that helps everything else fall into place.
For example, I’ve been to many conferences where guys wear blazers, and there’s always at least one person in a leather jacket with a dress shirt. He doesn’t look out of place, but he’s definitely making a statement. His choice to combine an edgy item with business casual is a deliberate decision about how he wants to be seen.
Similarly, I often dress a bit more formally when I visit my fiancée’s parents because I want to convey capability and respect.
If you’re going on a first date, your personal style becomes a useful tool. If you’re usually a formal office worker, you can decide whether to lean into that look or intentionally dial it down to signal something different. Even on casual dates, a well-put-together outfit can show off your social savviness, polish, or even a deliberate casualness.
The tricky part about sending signals with your clothes is that they might not always be interpreted the way you intended. A leather jacket with a dress shirt might look confident to one person, but "trying too hard" to another. An untucked shirt might feel effortless to you, but careless to someone else. Skipping a belt might seem modern and stylish to me, but unfinished to others.
However, dressing intentionally isn’t about getting it right every single time. It’s about knowing why you chose your outfit. Even if it doesn’t quite hit the mark, that clarity stops you from second-guessing yourself all day. That’s why I focus on being "intentionally dressed" rather than just "well-dressed."
Understanding the event’s context and then adjusting your level of formality to match what you want to communicate is crucial.
Finally, consider what feels comfortable today.
Once you’ve thought about the situation, the impression you want to make, and your desired level of dressiness, everything else starts to click.
Some days, I choose to wear nice penny loafers even when I don’t have to, just because of the look they add. On other days, I might really want to wear sneakers for comfort, even if loafers would be more appropriate for the setting. In those cases, I adjust the rest of my outfit to balance it out. It’s a constant give-and-take.
You’re always juggling these different factors. For instance, you can swap a hoodie for a chore coat to make an outfit look a bit nicer. Or, you can put a t-shirt under your shawl collar sweater instead of a dress shirt to make it more casual. Switching jeans for chinos can add classic polish without making you feel overdressed.
Comfort isn’t just physical, though. Sometimes an outfit technically fits perfectly, but it just doesn’t feel right to you that day. If you find yourself fidgeting or doubting your clothes all day, that’s a valuable piece of information. Feeling confident in what you’re wearing is a huge part of being truly comfortable.
And sometimes, your desire for physical comfort might clash with how you want to present yourself. You might reach for something familiar because you’re tired or anxious, but it doesn’t always help you fully engage. Other times, wearing something slightly outside your usual comfort zone can actually help you feel more put-together, much like how good posture follows a well-fitting jacket. This tension is also part of the decision-making process.
You don’t have to choose between dressing well and feeling comfortable. You can have both when you learn how to mix and match different pieces to create a balanced look. That’s the real benefit of dressing intentionally: it gives you more options, not compromises.
Dressing intentionally simply means you’ve thought about all these different elements. This framework helps you understand what those elements are in the first place. That’s what brings you freedom, not limits.
Because ultimately, how you choose to get dressed is how you choose to present yourself to the world. And showing up with intention, quietly and consistently, is what makes your style uniquely your own.