Saddle fit is widely considered to be a crucial factor for the health and performance of riding horses; however, there have been no studies looking at the agreement between professionals who fit and assess saddles. The aim of the study was to determine the agreement between Society of Master Saddlers (SMSs) qualified saddle fitters when statically fitting a saddle following the SMS guidelines. Twenty SMS qualified saddle fitter volunteers were recruited via social media and asked to statically assess the fit of the saddle following the “7 points of saddle fit” guidelines of the SMS in 10 horses. Descriptive statistics and Fleiss Kappa (as a measure of agreement beyond chance) were used to determine agreement between fitters. Agreement varied from slight to substantial between the different saddle assessment criteria with the assessment of overall saddle fit resulting in a fair agreement of k = 0.32. Substantial agreement was found for saddle clearance front (k = 0.66), top (k = 0.78), and rear (k = 0.81). Fair agreement was found for clearance of the saddle—side (k = 0.28) and how the girth straps line up with girth groove (k = 0.31) and panel contact (k = 0.38). Slight agreement was found for tree width and length (k = 0.12) and tree length (k = 0.12). Horse height in some criteria affected agreement. Agreement varied between the standard criteria. In cases where it was difficult to visually evaluate saddle fit, agreement was lower. Further work should aim to standardize the criteria which had suboptimal agreement.