Freedom in Tradition

[CMcG]

"The Highland dress is essentially a 'free' dress -- that is to say, a man's taste and circumstances must alone be permitted to decide when and where and how he should wear it... I presume to dictate to no man what he shall eat or drink or wherewithal he shall be clothed."
-- The Hon. Stuart Ruaidri Erskine, The Kilt & How to Wear It, 1901.

There are many threads here on Xmarks discussing the 'rules' of THCD; rules can be especially valuable in guiding a beginner through potentially very foreign sartorial territory. In my opinion, finding freedom within rules is where creativity lives...

For someone who already know the rules and has internalized them through experience, where does one find freedom within THCD? How does one express oneself as an individual within tradition?

Or is Erskine wrong, Highland dress is not essentially a 'free' dress, and there is no room for freedom, creativity, or individuality in THCD?