If you're like me and you suck at anything creative (I consistently failed Art in school), I'll give you another option...
1. Find a look on the following site that you would like to copy. Save the photo, because you'll use it as a reference when shopping for clothes. If you have a woman whose advice you trust, it wouldn't be a bad idea to get her to choose a look for you:
http://propercloth.com/collections
Order shirts to match whatever look you like from Proper Cloth, made to measure in your size. You'll get a better result if you can get to their store for a fitting. Order one shirt at a time so you have an opportunity to make adjustments.
2. buy chinos from Gap or Banana Republic - they both have safe, classic styles. You can take your reference photo and get the sales girls to find something which matches. Try 'slim' leg first. If they look or feel tight on you, go one step wider ('straight leg'). 'Relaxed leg' doesn't give a sharp look. Avoid anything with the word 'skinny' on it - they're for homosexuals.
I personally avoid jeans because they're too complicated. Gap and BR stores have maybe five styles of chinos, where as Levi's stores have probably 30 different jeans.
3. find shoes and a belt similar to your reference photo. If in doubt, post a photo of the shoes and the look you're trying to match here for advice. It's best to buy shoes and belts at the same store so the leather matches. WIA might know a good place to buy your leather in the US. I don't know because I'm in Europe and I order online.
4. the last step is the jacket.. it's the hardest part because jackets are a complicated piece of clothing and there are many aspects of the fit and style. By purchasing your jacket last, you can wear the rest of your outfit when shopping. That makes it easier to find something that matches. Again, don't hesitate to take your reference photo and ask the sales girls to suggest something similar.
I'll be the first to admit that I struggle with jackets, which is why I stopped buying them off the rack and went to a tailor.
By following these rules, you don't need to build up your fashion skills - you're basically just plagiarising someone else's creative work. Do it shamelessly.

You don't have to use Proper Cloth's catalogue, but since they are a shirtmaker, ordering one of their styles saves you having to learn about collars, plackets, cuffs, and all the other details of shirt construction.
In general, spend a lot on your jacket and shoes. Spending more on chinos doesn't make much difference. For shirts, it's all about the fit.
The last tip is optional... I print out my reference photos so that when I'm getting ready to go out I can just flick through my 'catalogue' and choose a look.