Urban open spaces have substantially contributed to the development of cities in terms of image, function, form, and social engagement, and thus have been a central concern of urban researchers for several decades. This paper contributes to the contemporary urban discourse as it relates to the city and its users. It demonstrates a mechanism for characterisation and systematic assessment of key urban open spaces in Glasgow City Centre. The mechanism is implemented in three layers of investigation that involve the development of space profiles through preliminary observations, an examination of functional, social, and perceptual attributes through a walking tour assessment procedure with checklists and a scoring system, and an understanding of how users perceive and comprehend these spaces through a photographic attitude survey. The paper places emphasis on key findings by conveying similarities and differences between the spaces in terms of assessment outcomes and users’ perception, while revealing their essential attributes and qualities. Conclusions are offered as reflections on the findings while suggesting possibilities for future research through additional complementary layers of investigation.