I'd have to say my favorite article of clothing is the jacket. Always has been, likely always will be.
Why do I have such a fascination with jackets? Because they not only keep me warm, but they also are the most noticeable article of clothing one puts on. I mean seriously, a jacket goes on TOP of everything else, covering any clothes you are already wearing. It's also one of the only articles you can take off or put on multiple times in a day. It allows you to effortlessly change your look whether you're outside or inside. Make sure you have an awesome one in your wardrobe.
Here are some jackets that I personally like, all different styles:
Just quick comments on the photos above.
Trenches make you feel boss, and will never go out of style. This is especially true for Burberry , since they invented trenches. Stick with tans, greys, blacks and navys, and make sure to find the right fit, since they'll last you a lifetime.
Parkas, like the wings + horns one above, are extremely versatile, and can be dressed up or down effortlessly. They protect you from the rain, and are quite utilitarian, with the pockets and all.
Matt Bomer from White Collar pulls this jacket off awesomely (is that a word?). I've always had a hard time finding leather jackets that fit me well, but the day I do, I hope it looks like the one above, simple and slim.
Lastly, I think John Varvatos makes some really creative, and quality jackets in his mainline collection. If you've got some $, or rather, $$$, I would take a peak; you might find one that sings to you.
In terms of brand recommendations for jackets, it really depends on the price range you're looking at. Jackets can get astronomically expensive, because designers know they can charge a hefty fine on them. They usually are constructed with thicker fabrics, have a lot more variance in design, and are bought more sparingly, thus people are willing to splurge more.
I recommend spending a bare minimum of $50 on a jacket. I don't think that's unreasonable, because it will last you a long time if you buy the right one.
At the $50-$100 range, I would probably recommend Land's End or Banana Republic with a coupon (easily accessible). Many snobs will gawk at anything from GAP Co., due to their mass production and inconsistency of quality. However, I think that you can get some great jackets here that are stylish and will last. I have a jacket from BR that looks like the parka above, and I love it. People compliment this jacket all the time, and I got it for around $80 bucks.
At the $100-$200 mark, I like Topman and Diesel. I am going to say that these two recommendations are mainly based on look, rather than quality. Not saying that the quality is bad by any means, but just know that I put a bit of weight towards design. I also have to plug in The North Face & Patagonia, where it's function rather than fashion.
When we get to the $200-$400 range, this is where I think one should spend to get a quality jacket that will last. Brooks Brothers and Polo Ralph Lauren have very high quality jackets, and have obviously been in the business forever. In this range, my highest rec goes to Barbour since they make a damn solid jacket, and you'll notice the quality is exceptional.
Between $400-$1000, many jackets start to look absolutely amazing. However, you are now heading into brand name snobbery territory, so watch out! Brooks Brothers Black Fleece and Ralph Lauren Black Label are two of my favorites.
$1000+: My favorite looking jackets come from John Varvatos Collection, Dior Homme, and Paul Smith Main Line. All three make very sleek, trim, European style jackets that I think can elevate your look. Be careful, as clearly you're spending a lot for the brand name, rather than the pure functionality of the jacket. Hey, but if you have the cash, why not right?
I'd recommend picking up a solid jacket for the fall. Whether you buy a parka, trench, leather, or wool jacket, find one that helps identify your image. It will get noticed.