October (and fall) snuck up on us real fast. And what that means is slightly chilly days lie ahead of us and it is also time for me to write a follow up on my what shoes to wear this summer post from earlier this year.

The nip in the air means that you can no-longer wear your flip flops or your slip-ons. The sneakers are nice, but it is time to rethink your shoe options. Here are my criterion for making decisions about autumn shoes:

• They should envelope the foot and ankles nicely. On a laced boot, six eyelets are the most you need during fall months.
• They should be made of natural materials. Suede is my recommendation, but again, it is a highly personal choice.
• They shouldn’t be heavy and comfortable to walk in. Lighter weight means you can get more use for them during the pleasant spring (April-May) season.
• Since most places in the US (an Europe) don’t really get snow during this time of the year, I prefer that you buy shoes with leather soles.
• They should match fall colors such as pastel colors or some shade of brown.
• They should fall somewhere between casual and formal, so you can wear them not only with your jeans, but also with corduroys, heavy twill pants and formal trousers. I wouldn’t be fashion forward, but still suggest something trendy: get wingtip boots. There are many options this seasons.
• They should be well priced. The type of shoes I like for fall are not cheap, but if you buy the right pair, they last for quite a few years.

Here are my top five picks for this season.

1. Alden’s unlined suede Chukka boots are my top recommendation. They’re not cheap by any stretch of imagination, but I am in my second year of owning them and they look brand new. They meet all the aforementioned criterion and they are actually very good during spring months as well. I would buy this style, any day, any time. It is the best pair of shoes I have ever owned. Here is my review from a year ago.
2. Clae Strayhorn Chukka Boots: For about $120 you get a sporty-meets-formal shoe that works really well with jeans and other casual trousers. The only downside: it is in black, but the crepe sole gives it a fall like feel.
3. Oliver Spencer Suede Chukka Boots: These are like Clae Strayhorn but from the house of Oliver Spencer who is one of the more eclectic British designers. So not surprisingly they are more expensive – about $210 a pair. The blue suede model that is being sold by Mr. Porter is the best of its kind. They are also available in red/rust color but are damn hard to find. Other colors are brown and black.
4. SeaVees 2 eye floater: This is one of the best casual shoe on the market. Made of suede it comes in two colors, gray and black. I don’t particularly like those colors, but if you do, then you couldn’t go wrong with this shoe. It is particularly awesome for folks who live in the Bay Area and wear jeans to work. Cost, about $128 a pair but you can find bargains on the web.
5. Allen Edmonds Haight Chelsea Boots: I don’t particularly like lace-ups so I always end up wearing the chelsea design of boots that are more equestrian in nature. I saw this at a store recently and found them quite attractive and well made. These have a slight wingtip design and are more formal. The shoe is a little heavy but it will also last well into the winter months, especially if it doesn’t rain or snow too much where you live. They are on sale right now for about $275-a-pair.

Now there are a whole bunch of other shoes that I like. For instance, I love the Camper Woody ($200-a-pair) or Tod’s Chelsea leather ankle boots ($765), but as far as I am concerned, if you have the money and like timeless classics, then go with the Alden Chukka.

PS: These prices and models are all US-centric. There are other excellent options in Europe and Asia, that might cost less or more, but there is no way for me to know.