For most of my life, I wore poorly fitted jeans and graphic tees (for me, t-shirts with a big video game logo or design on it). I don’t remember what shoes I preferred before I switched to Vibrams but I’m sure I grabbed whatever looked interesting and was cheap. I didn’t put any thought into my looks (check out My Story post) and you know what?
That’s okay.
What I didn’t like was never knowing my jean size or what fit I needed. Every time I went into the store I had no idea what I was doing and just bought something, maybe tried it on, and walked out with it. Sometimes they would be longer, or shorter and I wouldn’t really know what I was supposed to do.
Today, I want to put in more effort because I think I’m worth the effort. Also, I hate not being informed about something. I used to think clothes weren’t worth my time. Now, I want to find the perfect fit as well as something that is affordable but will last and look good.
So what do we do? Let’s start with the basics of casual style.
Casual vs. Relaxed
First of all, I want to differentiate between what I call casual and relaxed. Relaxed is sweat pants, and a Power Rangers shirt; this is stuff you would put on to lounge around the house or with friends, which I have nothing against.
Casual is a step above, where maybe you replace that tee-shirt of a nostalgic children’s show with a plain tee and put on some real pants (instead of just wearing shorts 100% of the time). You could go out and actually appear like you put a ton of effort into your look if you put together the right pieces.
Here is an example of a casual outfit of mine (that I wear for winter, hence double-coats):
I generally wear a collared shirt, button-down is good, polos or even nice plain tee-shirt. Jeans have been my go-to for awhile, but a new type of pant I never heard of has captured my attention: the chino. Honestly, it’s hard to tell the difference of the many kinds of pants out there. The wool chinos I wear (more dressy actually), are the most comfortable pair of pants I own so I challenge you to try some out.
Now that we’ve established what I think casual clothes are, let’s break down the basics.
Keep things Neutral and they’ll go with Everything
If you’re new to fashion like I am, there’s no rush to go crazy with style. Find something simple and comfortable and if it matches with everything then you can just choose whatever you want and it will look good. Rotation is important, so you can hang up your clothes in a particular order or just choose randomly. Either way, you want to look good without having to “overthink” it.
Another pro tip, lay out your outfit the night before.
As you build your confidence you can use the “change one item” technique to add additional color and style as you get more comfortable. For example, instead of wearing that plain grey tee-shirt with dark wash jeans and black Vans, try wearing a colorful shirt, or light wash jeans or blue Vans. You don’t have to completely alter your style to change things up. Keep it simple and it will generally match.
But what’s matching?
The Basics of a Casual Outfit
Shoes: could be some boots, sneakers, or loafers/mocs any of these are good for casual settings and can even be dressed up for work. If you stick with brown/black/grey you’re basically always good. Just make sure that your shoes and belt match (watch too if they’re all leather).
Belts: many belts come reversible with brown on one side, black on the other; however, I prefer Anson belts because they don’t use the classic holes; they’re on a track.
Pants: can’t go wrong with dark wash jeans. I am currently wearing Levi relaxed fit, but everyone’s body shape is different. I think I could fit into something more slim fit so I say experiment. Try a bunch on and bring a friend with you. If you go dark wash, it will once again, go with everything.
Shirts: I mostly wear checkered long-sleeve shirts (yes, they have buttons). These can generally be tucked or untucked depending on the situation. You can tell if you should tuck a shirt by the hem. Is it straight (think tee-shirt)? Then don’t tuck it in. If it has a bit of a curve to it it is optional, but make sure it doesn’t hang too low otherwise just tuck it in and roll up your sleeves to maintain a more casual look.
Jackets: There are a ton of jacket styles that seem to be timeless in the fashion world. I am currently rocking a Levi (pictured above in the fashion grid), and I recommend checking out jean, leather, and bomber as a few styles that I’ve seen that I would definitely wear. These are jackets that you can throw on and wear in most moderate weather. The only full coat I own right now is a black peacoat. I love it, especially because it’s black so I can wear it with everything.
Socks: I have heard mix reviews of white socks. Some people are all about them for the spring, some people say never wear white socks or only wear them with jeans. I am currently going all-black all the time, but with jeans any color is fine and if you can match with your pants (not your shoes).
What’s next?
I am currently working on building an interchangeable wardrobe which is: 4 jackets, 4 shirts, 4 pants and 4 shoes that I can mix-and match for 256 different outfits. I want to keep things simple and I enjoy some versatility in my clothing.
I am going to expand my colors to include different shades of green, which I will sprinkle throughout my wardrobe/accessories so that I can add a bit of color as well.
Is there a casual clothing topic you would like me to cover in an update?
Something of mine you want to see?
Any other questions you might have?
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DontCare Lifestyle 
