i do think that dressing well in some ways is determined by the type of body shape you have.
and i can see why models are models because clothes simply look better on skinnier people.
i am definitely not skinny so hedi's period dior homme clothes are not so much for me, i do often wish i am waifish though, tall lanky hands and legs.
and i do admire people for looking 'effortlessly chic' although i sometimes wonder if there is such a thing?
i also dont agree with not having enough money as a reason for not being able to look good.
i have seen many students who often shop at second hand thrift shops, vintage shops and turn out looking very good.
maybe they will wear a pair of old chinos with a jacket from old french army or something, probably not costing more than $20 for the whole look and they still look cool.
sometimes i think is also the attitude, certain clothes needs a certain attitude to look good in.
for myself, i sometimes note down the combination of what i think is good and repeat on other days. for eg. a certain sweater should just go with a certain tshirt cos the tshirt has the exact enough length to 'peep' from the sweater. if i dont do this, and if i am in a rush, i may not have time to dress properly, and i seem to be always in a rush