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If you'd still like to dress "better" in general, the /r/malefashionadvice subreddit has some solid resources on the sidebar that you should check out.
I am not affiliated with her or whatever, just follow her advice myself and enjoy her content.
Man or woman, I'd ask a female friend for help. In my experience women have much better eyes for dress than men, for either men or women actually. See if you can't convince someone to come along shopping with you, the second opinion is very valuable.
He does this once every year now. The difference is amazing. Caveat: she actually looks better dressed than most women.
For example -- keep wearing jeans, but buy a couple pairs of nice, dark/black well-cut jeans.
Instead of wearing a sweatshirt hoodie, wear a nice pullover sweater (H&M sells a nice waffle-texture sweater for fairly cheap, I got mine on clearance for $5 and I've worn it for years now).
Button-ups can easily look too formal, but flannel is a good middle ground.
Some nice-fabric solid-tone tshirts are a good basic, as well.
Now that you have a few pieces, you can mix-and-match as well. Sweater + flannel underneath, unbuttoned flannel with tshirt underneath, etc.
For shoes, instead of wearing cheap running shoes, find some nicer-looking neutral-color sneakers (might be worth looking thru https://www.reddit.com/r/Sneakers/comments/2e9b1o/we_should_..., but I can't vouch too hard for it). Depending on your style, you might also want some boots -- I have some big black Doc-esque boots that I love, but brown is a less-punk choice that's a classic.
FWIW: I'm not a guy, but this advice is pretty gender-neutral.
Good luck!
Unless you want to put a lot of effort into this then just buy clothes with the best quality fabric you can find (you can tell quality fabric just by feel). Not only will your clothes feel great, as a side effect you will be stylish without being fashionable. Quality never goes out of style. Edit. I should add that top quality fabric is never wasted on "fast fashion" so the clothes will always be a bit more conservat…
How do you define best quality fabric?
Edit. A lot of designers will make a limited number of items with fabric that is much better than the pricing point would suggest. My guess is they have dreams of being in Paris or Milan and so sneak in more quality than the collection calls for on a few items - the "yes most of my designs are compromised by commercial concerns, but look at this one shirt" effect.
Then, clothing is a form of expression. It expresses an intention on how you want to be perceived (at a superficial level at least).
Regardless of style:
- Pick clothes that fit your size well.
- Some clothes may require some extensive ironing, especially shirts. If ironing is not for you, our you want to minimize your time ironing, have this in mind.
- Some clothes may not be able to be washed using home appliances and may require dry cleaning, etc.
- Colors and patterns matter can affect your perceived weight.
This worked like a charm for a friend of mine in college: Go to a clothing store and buy exact sets of clothing off of the mannequins that you see. He knew literally nothing about fashion, but was consistently complimented on his clothing.
This is a surprisingly good approach especially at stores where the person dressing the mannequins has some sort of clue. The only downside is you will often end up with sets of clothes that can't be mixed and matched well.
Yet another one is that you will often buy clothes very specific to that year's collection and will look outdated soon.
Mannequins rarely are with the cheaper and/or classic clothes.
Earlier quoted context omitted.
This is a surprisingly good approach especially at stores where the person dressing the mannequins has some sort of clue. The only downside is you will often end up with sets of clothes that can't be mixed and matched well.
Another downside is that you will mostly buy the most expensive clothes in the shop. Yet another one is that you will often buy clothes very specific to that year's collection and will look outdated soon. Mannequins rarely are with the cheaper and/or classic clothes.
My actual advice is buy the clothes with the best quality fabric.