I want to just go over the basics such as the fit, the fabric and the colours of pants you should make sure you have in your wardrobe. Remember this is just the essentials, or shall we say the bare minimum guide.
You can always get more pants if you desire, you can even get creative afterwards. For now of course we want to cover the basics.
Now I may not have stressed this point, but I will. The fit of your pants is very important. Not the most important, but it goes a long way for guys. If you must pick between two sizes that don't fit perfectly, choose the baggier pants. It can be tailored in. For future reference you should know your true waist size (I), your inseam (E) and length (F). When shopping at a men's stores you will have a wide selection of pants and the 3 measurements listed above will vary. These measurements are normally not the same as your jean sizes. The final aspect of the fit is the crotch area (D) which measures from your waist button around to the back side. Usually around the 13 to 16 inch area. Ensure the fit is comfortable for you. Higher rise (tighter crotch area) is in style but you should be conservative because you have no idea what the styles will be in 2-3 years. Further expressing my point that your first couple pieces should cover the basics, after that go nuts.
This brings me to one quick point, Our parents may have worn pants at their natural (around belly button, see below) waist but I prefer not to. I have a gut :( and it does't make me feel comfortable. It is up to you. Most men these days seem to wear their dress pants like a pair of jeans.
The second aspect of my guide on pants is on basic fabrics. For the most part you should purchase your first couple pants made out of 100% wool. You can drop the price a bit by buying a wool blend but I don't recommend it. Of course depending on your climate buy wool with the appropriate stitch count. Which by the way is a great question to ask the sales agent to see if he knows what he is even doing. Higher stitch counts are perfect for warmer climates but can be pricey. This is where a blend may be appropriate. Lower stitch counts (80-100) are sufficient to get through the colder climate areas such as Canada! 
Now above I have already shown you which colors are perfect to start off with. A light gray, navy blue and either charcoal or black. I prefer charcoal as it is not as formal. Also a quick point, buy pants that have no pleats on them or are called flat front. Buying pleats these days is unnecessary and I don't see why it will come back into style anytime soon.
Besides these basics there are always those casual Fridays that we need to dress nice for. No offense to Wrangler, Lee or Levi but they just don't accomplish the same level of sophistication as a pair of say diesel or se7en jeans. The color of the denim just looks a bit better and does not fade as quickly. Now as I write this I'm coming off a bit snotty or arrogant, but my logic for spending top dollar on jeans is that we wear our jeans quite a bit. There is no shame in paying a bit more for them. I am proudly cycling through three pairs of jeans for over 4 years now and I'm glad they continue to look and feel the same and they continue to stay in style after all these years.
Finally the Khaki's. I personally would try to stray away from Khakis as much as possible. We are trying to dress as well as possibly can to work and Khaki's are second fiddle to trousers. I highly recommend putting your khaki's away for those cold golfing trips you may go on.
Other Installments of Guide
- The Guide
- Trench Coat & Pea Coats
- Sport Coats & Blazers
- Pants & Trousers
- Dress Shirts & Polos
- Sweaters
- Belts, Shoes, Scarves and Gloves
- Finally, Color Combination
cover photo courtesy of: http://www.nitafashions.com/style_mensuit.htm
body photos courtesy of google images
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