I just pay $12/year and subscribe to "Nylon for guys" magazine (http://guys.nylonmag.com/) - it really does do all the work involved with "staying current" so you don't have to look like this guy: http://yogan.meinungsverstaerker.de/fun/80s1337ness.jpg
Also, I wouldn't consider the last photo of you to be "haute couture": you're just copying Steve Jobs with a little bit of hair gel.
You may be a hipster. http://www.urbandictionary.com/define.php?term=hipster
"Listens to bands that you have never heard of. Has hairstyle that can only be described as "complicated." (Most likely achieved by a minimum of one week not washing it.) Probably tattooed. Maybe gay. Definitely cooler than you. Reads Black Book, Nylon, and the Styles section of the New York Times. Drinks Pabst Blue Ribbon. Often. Complains. Always denies being a hipster..."
Once you have a girlfriend, dressing fashionably is rather easy and mainly because I'm no longer allowed to choose except between Brown Shirt #1 and #2.
Girls like guys who look nice for the same reason guys like girls who look nice: it's more attractive.
It's another set of rules to play with, another system to hack. Learn the game and have some fun, that's what I did.
I live in Vancouver, so maybe that is different from the valley.
Some of my friends are the Yaletown game developer nerds. This probably describes me. I like my Pumas and Lacoste shoes. When Douglas Coupland described the "Nikumas" in his book jPod, I almost fell over from laughing because he described the situation perfectly. The rest of the attire fits the shoes. Think Kanye West's outfit.
I know the Gastown web developer nerds too. They wear their Skechers and other hipster-nerd shoes. The rest of the attire matches.
Unfortunately, reading fashion magazines doesn't really improve a person's style unless you already look like a fashion model. San Francisco is filled with programmers who wear expensive, trendy gear and they don't look much better than the hacker slobs because it doesn't really suit their body shape or personality. In fact, they look like posers who spent $50 on a too-small t-shirt and $200 on sneakers that look like aerobic trainers from a B-movie about the future.
Simple, clean clothes that suit your body shape are a better bet. Most guys would be doing themselves a favor by donating their wardrobe to goodwill and spending a few hundred dollars buying some fresh basics.
Launch and get funded. Then no one will care what you're wearing.
Robert Winston has a piece in his book "Human Instinct" where he was looking at the effect of "funding" on his attractiveness to women. Day 1, he turns up in old clothes, in a clapped-out motor car and generally unkempt appearance. Scores about 4-5. Next day, he's back in a flash car, expertly groomed right down to the manicure, and he gets average 9 out of 10. The most telling part was one of the female test subjects saying "Well, I really liked you better yesterday, but I gave you a higher score today."
So, yes, money is not important and it's all-important. Dressing well shows you have it, but so do other things. It's up to you to decide if you care. Personally, I don't.
What are you going to do when your startup is successful and you're rolling in money? If you want to be out in the world, pursuing varied interests (or women), looking nice helps.
Appearance is continuous with reality. Imbalance in your intellectual life, for better or worse, tends to reflect in the way you appear. Looking nice is an indicator that you value social connection with others.
This is never true. The impact of dress on perception is well studied and it is large. If you're not dressing well, you are foolishly giving up an easy edge.
A somewhat overlooked subject is coworker dress as a workplace quality issue. A lot of geeks don't notice dress, but most other people are sensitive to the aesthetic presentation of the people they have to spend many hours a day with. Going to work with very well presented people is a job perk, and having to interact with slobs is undesirable. Realize that even if you don't care about dress, other very competent people you may work with will care. Tacky clothing and pasty physiques can be like second hand smoke.
But without the cancer risk.
