We're previewing the holiday shopping season with a series of articles on how to make the most of Cyber Monday -- online retail's answer to the day after Thanksgiving.

Once upon a time, my holiday shopping was simple. I worked in the town of Boston, where I had a cozy office all to myself. In that cozy office was a large, dark, wooden file cabinet that was nice to look at but rarely used. I started shopping early in the season, buying presents at Downtown Crossing, Boston's big urban retail district a three-minute walk away. I stashed my presents in that file cabinet, wrapped them in bright paper there in my office, and brought them all home a few days before Christmas, ready to stick under the tree.

That was 10 years ago. Fast forward a bit to December 1999. My wife and I aren't living in a tiny apartment too small for gift hiding places -- we've got a good-sized house. And we're about to have babies -- yes, babies: twins, due any moment. I worked in Boston's suburbs, far from big retail outlets. And with my hugely pregnant wife home on leave, extremely uncomfortable, and all but immobile, and with last-minute baby preparations (read: home renovations) in full swing, I wasn't exactly overwhelmed with free time.

So, naturally, I did all my holiday shopping online. Except that back then, it wasn't "naturally" -- it was still something of an adventure. I wasn't new to online shopping, having made my first online purchase in 1997 at Amazon.com (NASDAQ:AMZN), much to the horror of friends who worried that "this whole Internet thing" was in fact a giant credit card fraud. But I was skeptical of the idea that I could get pretty much everything I wanted online. Would everyone end up getting books for Christmas?

The power of "e-commerce"
To my surprise, nearly everything on my shopping list was available online -- at good prices. The digital camera, the cute boots my wife loved (but that never really fit her post-pregnancy feet, alas), beautiful china for my mom, a CD player for my sister, assorted baby supplies -- I ordered all of it online, mostly at the last minute. Some of it even came wrapped. (And the twins? They held off until early January, which cost us a double-barreled tax deduction for 1999 but gave us time to get the house ready for them. Whew.)

It's old news now, of course, but then it was kind of shocking to realize that the transition to "e-commerce" (as we called it back then) was pretty much complete. Many vendors at that point were iffy startups, and many wouldn't survive another year. But established retailers like Nordstrom (NYSE:JWN) and J.C. Penney (NYSE:JCP) embraced the new medium with lavish sites that offered thousands of items -- and a trusted name on the virtual front door.

Even my technophobic friends caught on.

The limits of holiday shopping online
Of course, shopping online has limits. No matter how good the vendor's site is, some things -- the texture of a sweater, the color of a scarf, the size of the gemstones in a pair of earrings -- just can't be communicated perfectly via the Web.

So today my approach looks like this:

  • Clothes. If I know someone's sizes, and I know they generally like things from a certain vendor -- Sears Holdings' (NASDAQ:SHLD) Lands' End unit, for instance -- I'll order with confidence. If I'm less confident, I'll shop the old-fashioned bricks-and-mortar way so I can see the colors and feel the fabrics before I buy. I absolutely hate giving gift cards, so I avoid that route unless I'm completely stuck.
  • Miscellaneous consumer items. Books? Gadgets? Camera supplies for my shutterbug spouse? When I know exactly what I want, I order online. It's usually cheaper and always more convenient. As far as I'm concerned, this is a no-brainer.
  • When I need ideas. I have mixed results browsing for gift ideas online. Many sites have tools for giving recommendations, but none has managed to bottle the browsing experience you get from wandering through a mall, say. On the other hand, if I can come up with a basic idea -- "Dad needs new stereo headphones," for instance -- I can do the research on Amazon or a similar site and find a recommended item that fits my budget.

In the end, it comes down to two factors: How picky are you about the gifts you give, and how crunched is your time? While the online experience continues to improve every year, it's unlikely to replace the bricks-and-mortar-and-huge-holiday-crowds experience for many -- but if you hate crowded malls, or are short on time, holiday shopping has never been easier.

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Fool contributor John Rosevear welcomes your questions and comments. He does not own any of the stocks mentioned in this article. Amazon.com is a Stock Advisor recommendation. The Motley Fool has a beribboned disclosure policy.