Your clothes are communicating about you whether intended or not. Decide what you want to communicate about yourself through your clothes first, then choose looks and pieces accordingly.
You don't dress with an intention to “impress.” You have nothing to prove. Aim to dress to communicate the real you.
Your clothing can elevate your mood, boost confidence and positively hack your self-perception. Good style is a form of positive self talk. Poor appearance undercuts you.
It's simpler to ruin a first impression with one inappropriate item of clothing or accessory than to enhance it with a single piece. Be mindful of every item on your body.
Don't make physical comfort your main consideration when putting outfits together.
Style Direction Tips
Keep it simple.
You don't need luxury brands.
You don't need a large wardrobe. Most men typically rotate between just a dozen base items.
Get mileage out of wardrobe by selecting pieces that are interchangeable. I.e. go classic.
You don't need "statement" pieces in eye-catching colors or wild prints. A little bit of texture or fine-scale subtle patterns go a long way.
Got a wild side? Cool. Let your personality show how funny and off-beat you are. Not your clothes. And definitely not your socks.
If in doubt, stick with a neutral color palette. Red & yellow get into clown territory. Avoid.
Always be dressed well. You never know when you you'll meet someone for whom it matters. "Dress well" doesn't mean "dress fancy". Example: casual doesn't have to be sloppy or drab.
Don't want to think about what to wear every day? Consider a minimal Personal Uniform. A common example is dark jeans and dress shirts as a go-to base. Get a number of pairs of dark jeans and then just rotate the shirts -- white, navy, black, light blue. They'll all work together.
Embrace your age as a mature man. Avoid trendy or street looks if over 25.
Be skeptical of trends. Don't chase them. Classic looks are more masculine.
Items in black visually slim the body; items in white visually broaden the body.
Nothing you wear should draw attention away from your face.
Since the average guy dresses without much thought, it is super simple to be considered stylish: e.g. go with jeans that fit, solid color shirts, all white leather sneakers or nice boots, real sunglasses not Oakley's and a legit watch.
Does it make sense that you want a pretty girl, but you wear ugly clothes?