Will at A Suitable Wardrobe once commented that when he first started learning about clothing, he learned by observing others. Which is exactly how I’ve learned as well. Unfortunately, it’s difficult to find stylish men these days, both in our daily lives and among celebrities.
One of the best sources for inspiration, I’ve found, is online at sites such as StyleForum, where menswear enthusiasts post pictures of their daily ensembles. There are three main threads for such activity – one for traditional men’s clothing (suits and the like), casual clothing for men who typically wear suits on weekdays, and streetwear for those who don’t work in traditional business environments. All three are pretty active, so unless you’re checking them often, you can easily miss some of the better posts (such as yesterday’s post by member maomao).
If you’re just a casual observer, you can view some of the “best of” threads that people have put together. These are typically put compiled by highly active posters, and are of course subject to their taste. Still, they’re pretty good for the most part. The most celebrated of these is a digest by member Voxsartoria. Unfortunately, it’s no longer active, but the digest is still very fun to review. There have also been “best of” threads started by members gdl203 and Trini at the traditional side of the forum, as well as one by Lel on the streetwear side. Lastly, some of my favorites have been collected at the blog Stulen stil. Not every picture on there is from StyleForum, but many of them are. Comb through these threads to find what you like.
Learning how to dress well typically starts by figuring out who inspires you. Ignore fashion street style shots that seem to focus more on products than ensembles. Once you find a few inspirational figures, pay attention to how their clothes fit and how they coordinate and harmonize the pieces they wear. Emulate them until you can confidently do the same with your own sense of style. This may take a few years’ time, and perhaps a few rounds of clothing purges and acquisitions (good fits are hard to achieve), but you’ll get the hang of it soon enough.