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For the most part, fleece jackets and vests should be avoided as they are overdone, unstylish, and usually just bought because they are a cheaper alternative. Also try to avoid jackets that are over-designed -- excess of zippers, buttons, or straps; epaulets (unless it's army surplus); several pockets which would likely go unused; unnecessary belt straps; and very flashy designs in bright colors. The style of jacket/coat which you may find yourself using is usually heavily influenced by the style you are attempting to use (e.g., you will not see a man interested in menswear wearing an oversized orange parka). As a general rule of thumb, until you know what you're doing, try to keep outerwear darker than the tops layered beneath.

When it comes to brands, don't be shy to only go for what you can afford as outerwear can easily end up being one of the most expensive pieces in an outfit. Even though you'll find several anons who detest the name, The North Face isn't an entirely bad place to start off with outerwear, so long as you don't mind the obnoxious branding and avoid the over-designed jackets. To find the best, though, you may have to search if you aren't satisfied with the brands in Brand Reviews as most people on /fa/ aren't too knowledgeable on the subject of who makes quality outerwear and what an appropriate price is.

Leather jackets are fine just make sure they aren't complex and that it goes well with the weather and your outfit.