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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.
Honestly though I'm 40 and I wear jeans and a t-shirt. I've been working as a developer for 20 years. When I started the jeans and a t-shirt thing was not accepted like it is now.
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…
(1) If you go to a nice department store like Nordstrom, I believe you can still make an appointment with a personal shopper. That might be the best way for you to try new styles while also getting to feel the fabric in advance and get clothes that fit you well.
(2) If there are people you think dress nicely in a way you'd like to emulate, compliment them! They'll appreciate it. They might tell you where they got the outfit. And if not, you can ask.
(3) If you go to a clothing company's website like JCrew.com, they'll have a lot of pictures of people wearing full, stylish outfits, that might start to give you ideas about how to put your own outfits together. On JCrew I believe they even have a page called "What to wear" with links to all the items in each picture.
Good luck out there!
- Look at what people wear when you walk around the street. Who dresses well? What do you like about their style?
- Try on lots of different clothes, including stuff that you wouldn't normally wear. What works? What doesn't? Why?
- Get a full length mirror. Look at yourself before you leave the house everyday. Take some time to try on outfits, how can you combine clothes you already have into new outfits.
- Most important -> Have fun, and dress for your taste not what you think others want to see.
Take cues from how most people dress in the office and target that level of formality. If most people are t-shirt and jeans, just stick with what you're comfortable in. If most are jeans and a button-up shirt, do that.
Yeah, it's conformity, but if you're concerned your attire is affecting your perception, the easiest way to fix it is to match everyone else.
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.
The only downside is you will often end up with sets of clothes that can't be mixed and matched well.
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.
Looking at most husbands I would disagree with this statement :p
Find "your colors" - i.e. general color directions that look good on you. Ask people (typically women because they tend to be interested in such topics) what colors they think would suit you.
I made a decision a long while back to never wear tshirts again. After a certain age they look sloppy, not cool. I always wear a collared shirt. Equally I never wear short sleeved shirts - I roll up the sleeves of long sleeved shirts on hot days.
Get some nice brown leather shoes and some nice black leather shoes.
If you live in a cold climate buy several smart jackets including some leather jackets.
Other people here have suggest flicking through mens fashion magazines like GQ for ideas.
Start noticing what smart looking men are wearing.
Get several high quality white collared shirts and several high quality black collared shirts, these will go with a nice pair of slacks.
Buy a suit and not a cheap one - get it properly fitted and try on at least six suits before you buy one - wear it without a tie when you are going out with one of the white or black shorts mentioned above.
Accessorize - get a nice watch and belt.
Keep your hair regularly cut.
Don't buy cheap clothes - this is important. Having said that, do buy quality clothes that are on sale, or find factory outlets that sell the high quality brands at lower cost.
Fashion changes a lot from one group of people to another. That's why it is important to emulate someone from the same group.
Emulate is important, as you don't want to copy and look exactly the same.
That you like is important, because it shows when you are not comfortable on some clothes. Wearing something you don't personally like would be "trying too hard".