So You Want to Dress Better? Here's How.
Why would anyone want to dress better?
There are a multitude of different reasons as to why someone like yourself would want to upgrade their style. Maybe you're trying to impress someone. Maybe you aren't being taken seriously by others around you because of your clothes. Maybe you just want to make a change in your life. Whatever the reason, the simple fact that you're open to change is huge!
We're going to jump into the style advice, but first let's cover a couple things. Chances are, that if you're reading this article, you're male, between the ages of 20-35, and have an average build. I am in no way trying to alienate anyone, I'm just saying that my previous description is statistically the most likely scenario. If you don't fit into that bucket, don't fret, you can still get a lot of value from this post and series, but just know that you may have to adjust some things here or there.
Where do we begin?
You've already taken the first step in your style journey. You're doing some research and reading this article to find out the best way to proceed. But there's a ton of information out there and where do you go from here?
Start with your why.
You have to figure out the reason that you want to dress better. You have to know what the purpose of this style journey is going to be. I can't determine it for you, but here's how mine started:
I grew up in Hawaii. What this means is that I really was never taught a sense of style when I was younger as everyone simply wore a t-shirt and shorts everywhere. The most "dressed up" I ever got was a pair of jeans and an Aloha shirt. I went to college/university in Washington state and my need for a more diverse wardrobe happened immediately. I had no idea where to begin, so I simply grabbed the clothes I wore when I visited my grandparents and thought that would be enough. Boy was I wrong. I looked like a homeless guy mixed with the most confused stylist ever. I had no idea what I was doing. I was never overtly made fun of (being 6'4 helps with that), but I could tell I was getting weird looks. I cared about what other people thought so I decided I needed to make a change.
I googled things like, "how to dress better," "how to look cool," and other silly things like that and I got a whole lot of nothing. I figured there had to be a better way, so I just hopped on google and looked at what movie stars were wearing. They made it look so simple and easy! Hell, I could do that. Then I realized I had the bank account of a broke college kid and realized I had to figure out my own path. That's where my journey started.
I was tired of getting funny looks. I was tired of sticking out like a sore thumb. But most of all, I was tired of not getting girls because of the way I dressed. Shallow, but important to 18 year-old me.
You have to find your why, or else you'll give up.
...Still here? Let's move on!
The Foundation
We're going to really jump into the nitty gritty here so I hope you're ready.
This is the number one rule to better style.
Fit is the most important quality!
What does this mean? Well it means that no matter how great an item may look on a mannequin or on the shelf, if it doesn't fit well, it's going to look terrible. A $2000 suit will look terrible on anyone if the fit isn't right, but a $200 suit that fits like a glove will get far more compliments than the ill-fitted, expensive suit. If you learn nothing else from me, remember this: Fit is the most important quality of any item.
So what's the difference between a "good" fit and a "bad" fit?
A perfect fit is going to be snug but not too tight. It will hug your form perfectly, but it won't suffocate you. It will accentuate your great features while covering up your less than stellar qualities. In essence, perfect fit will make you look perfect!
Building on the Foundation
Now that you know that fit is the most important aspect to bettering your style game, let's move on to the basics.
I have to interject here and say that the advice I'm about to give works for me. It may not work for you. Your body is different than mine. Your taste is different than mine. You're climate is different than mine (probably). Take the principals and apply them to your own situation. That's all this is.
Here's my most basic outfit:
Jeans
T-Shirt
Flannel Shirt
Shoes (we'll get here eventually)
Suuuuuuuuper simple, but it works for me and it's clean.
The best part though? It's relatively cheap depending on how big you go on the shoes.
Let's go over each piece one by one.
- Jeans - I opt for Levi's dark wash jeans. I prefer a stiff denim since it ages better, but it's up to you. (If you want to go super deep, just google raw denim and go down that rabbit hole for a few hours... or days!) I always go with a slim cut, since I'm tall. If I go skinny, my legs look like toothpicks. Baggy went out of style years ago. Who knows if it will return. My go-to: Levi's 511 Indigo Denim Jeans
- T-Shirt - I'm a simple v-neck t-shirt guy. I have tried a ton of different brands, styles, colors and tend to go with solid colored varieties with a modest V (I have a lot of chest hair and nobody needs to see that poking out of a t-shirt). I've even had decent luck with Kirkland brand undershirts if you're not planning on taking off the flannel. My go-to: American Rag Solid V-Neck
- Flannel Shirt - I love flannel shirts. They don't work too well in the summer months, but for the other seasons, they're perfect. I usually go for a classic checkered pattern, but limit the color palette to two or three complementary colors. I've had really good luck with Uniqlo, but their clothing varies wildly in fit among the same size (not all larges are exactly alike). If you're looking for a low cost option, Uniqlo is the way to go. My go-to: Uniqlo Checkered Flannel Shirt
- Shoes - These are their own damn category that we will get to in another installment, as this can dress up or down an outfit. My go-to: Either White Stan Smiths or Black Nike SB Stefan Janoski
So that's it for the first installment of this series. I haven't completely figured out what all the installments are going to look like or what the order is going to be, but I would love to hear your feedback on things you would like to know or learn more about. There will certainly be an entire article dedicated to shoe style, as well as one dedicated to more "work appropriate" attire, but beyond that I'm looking to you folks for guidance.