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Few reasons why Chelseas work so well:
Originally Posted by Impulse
-Seamless, smooth transition between shoes and jeans, when wearing slim/skinny jeans. Most other popular designs, like sneakers, create an angle that makes them visually "stick out", it's a lot smoother with Chelseas.
-Highly versatile in terms of images that you can create with your outfit. They work with both dressier and edgier styles.
-Just simply looks great (though I recommended avoiding designs with round toe)
-I actually own that first pair and what I love to do is match the navy panel on the shoe with a navy scarf, little details like that make all the difference.
In terms of colors: black, brown, grey - all solid choices.
Just keep in mind that if you're going for suede (as your second example), they can be a bit a pain to look after and not suitable for wet weather (might be an issue in UK )
Counting by compliments that a pair got me:
Chelsea boots >> Grey biker suede boots > Red & white converse > Dark brown combat boots (I think combat boots could be close to the top too, but I just hadn't had really great designs myself) > Others