from the guy who began with no knowledge at all.
Dressing well, being stylish, taking time to craft a personal style— it’s all worth the effort, and I will take that to my grave. Turning the act of wearing clothing (something we already do, literally, every day) into a tool and brand that exudes confidence has noticeably changed my life. While the upsides are obvious, the truth is it starts out as something that takes mental effort to overcome. For some, it’s the idea of showing publicly that you’re learning and not necessarily where you’d like to be, and for others it’s the idea of making it seem to others like they’re “trying too hard.” Not only that, but it usually means shelling out hard-earned money to buy clothes that you’re not even one-hundred percent positive you’ll end up wearing. Whatever the reason or hesitation, it’s an exercise I feel can yield valuable return on the investment of time and money. I’ve outlined a framework for beginners below, and this is by no means comprehensive — that’s intentionally so. It is, however, what I found to be helpful in learning how to successfully project my confience and create a personal brand with my outfits. Keep in mind, too, that this is not a guide — this is too broad a subject to condense into a guide to follow. This framework, though, seeks to minimize cost while maximizing evolution.
A little disclaimer: I reject the idea that there is a universal “right” way to dress. Whatever you enjoy, whatever your style is — that’s the right way for you. I have nothing against sweatpants and baggy shirts, and there’s nothing wrong with a tailored suit and crisp tie. With that being said, they can be executed well, and they can be executed poorly.
Second disclaimer: this guide also appeals to no gender and no idea of gender.
Without further ado…
1) Know what you‘ve got (and what you like) before buying anything new
It’s tempting to feel like your current wardrobe is not enough and that “everything must go.” That’s moderately expensive, and works for some people. For most, this isn’t the time to think about what you need to add. That comes later. This is instead the time to instead take a step back, refrain from impulse buys, and look what your current style really is. How would you describe it? It doesn’t need a name, either — when I started getting interested in fashion, I could best describe my wardrobe then as graphic tees, plaid cargo shorts, jeans, and a dress shirt or two for special occasions. There’s a beautiful portrayal of it further down the page.
Defining your style, even in the simplest way, is crucial because understanding your personal style and how it fits in to your life can help you understand what to start wearing. Do a lot of networking? Make sure your business-casual attire is strong. College student? More of the basics. Making note of this will save you a lot of time later, and help you visualize what your ideal style is going to look like.
From there, take a look at an item or two what you really like. For me, it was one specific pair of cargo shorts. It wasn’t the cargo part that appealed to me, but rather, the pattern. I found myself wearing that specific pair a lot. Once I had found my favorite thing, the one “staple” I kept coming back to, I realized that’d be the easiest thing to branch out from, because I already enjoyed wearing it. Eventually, your wardrobe will only consist of things you love to wear — items that give you a massive confidence boost whenever you wear them. It would be easy (and expensive) to throw out everything that doesn’t fit that criteria, but for now, let’s just note what we love.
2) Take a half -hour or so and browse the website of the item you picked
The goal here is not to get lost in the endless depths of internet forums, shopping websites, and albums of inspiration. While that does help, it’s easy to get distracted or overwhelmed. Take a bit, browse around, note what you like and don’t like. Get an idea of what the brand’s stuff looks like, and whether or not that’s something you could see yourself wearing. When I was getting started, I ended up trusting the outfits they showed more than I trusted myself. It also helped me at the start to bookmark photos of style influencers who I though had great outfits. I kept the one thing I picked in mind — would that new item of clothing work with that thing? Would it work with what I ideally wanted my style to be? Making it something that gels well with your favorite pieces now is great, but make sure it also looks forward. The good news is that you’re still just researching. But…
Getting too invested in just the research is a rabbit hole you don’t want to go down. All of this valuable knowledge you’re getting about your style and preferences is useless if you don’t act on it. This is a great time to dream, to visualize — to close your eyes and think about what you’d like your style to look like in a month or a year. Placing yourself in the shoes of your future self can be one of the most powerful compasses for what you end up purchasing. Just so you know…it doesn’t have to be perfect. What I wanted my style to look like by senior year of college and what it ended up being are two completely different things, and I couldn’t be happier because of it. But I still took that important step of beginning with the end, the goal, at the front of my mind.
3) Act on your newfound knowledge: go to a store, and try on what you like
Learning to dress well on your own is truly a marathon, not a sprint. With that being said, true progress starts outside the comfort zone. You’re not going to make the real progress by just reading fashion blog posts (like this one!) or looking at pictures of what you want your style to be. You’ve got a sense for what you like, and now it’s time to act on it. The crucial, continuous step involves stepping outside your comfort zone and getting out to where you can make actual decisions about your wardrobe evolution. Get out to a store (ideally, one you’ve got easy access to, or has clothing you like, or both) and look around. See what might go well with your personality and current style, or what might help you get to where your style wants to be. Fit is important here, because how you want your clothes to look on you is entirely up to you. Baggy, tight, mix of both, looser, whatever you like. If you see something that you think fits the definition of what you want your style to be (and fits with what you’ve got now) then pull the trigger. Again, don’t buy ten things. One or two to start is good. I almost never buy more than three items at any time, no matter how cheap they are.
4) Slowly work the new item into your wardrobe
Wear it, get opinions, lather, rinse, repeat.
At this point, outside of your gut, your number one resource will be the opinions you value — friends, coworkers, and in my case, family members. You’re going to wear the new outfit, and, inevitably, people will comment on it. Own it, whatever they say. No one really paid attention to what I started wearing (well, besides my lovely mother) so I really had to base it off of what I felt confident wearing. Some people will be honest, and that’s great. Those people are your harshest critics and the most valuable input you can get. Seek as much advice as you can, including asking yourself the hard questions. Does it feel like what you’re wearing is truly something you can fit into the style you’d like to have in a month or a year? Or is this a placeholder — something to get you there. Think about this carefully. Once I felt confident (and it can take time) I safely placed the item in my wardrobe. On to the next one. Above all, you need to accept that you might, and probably will, be wrong. “Failure” will happen. And that’s okay. That’s how we learn. How is failure even defined when you’re learning to dress well? For me, it was buying clothing that was too small because I thought that was in-style, and buying the wrong cheap stuff. Those were expensive failures comparatively, but I still learned because I found out what I did and didn’t like. By taking a methodical approach, the cost of that failure is minimized, while learning is maximized.
Ultimately, it’s going to take a while to master your own style.
It took me about half a year to be truly more confident. Blogs, fashion magazines, friends — they’re all good outlets and inspiration, but the true change and direction is going to come from within eventually. I’ve included a few helpful links below that helped get me started, and future pieces are going to include guides on specific styles for men, but taking the framework above and applying it to how it fits into your life, budget, and lifestyle can get you on the right track. As always, feel free to reach out to me with any questions — I would be happy to give outfit advice and feedback.
/r/malefashionadvice: Where I started, they offer great, anonymous feedback and their biweekly “What Are You Wearing Today” posts are where I first got my inspiration
/r/femalefashionadvice: Same as above, but for those who identify as female
dressed.so: Anonymous fashion advice in one website. Essential resource for second opinions. Really helped accelerate my styles
“Looking Fly On A Dime”: one of the best frugal female fashion blogs out there
brokeandbespoke: similarly for men
putthison: just check it out