Oakeshott became interested in arms and armour as a boy. He started collecting swords while he was still a boy at Dulwich UK school, building up a significant collection. In addition he was an artist and illustrated most of his books, and was also a speaker.

Main article: Oakeshott typology

Oakeshott's typology of medieval and early renaissance swords is among his most influential and most lasting works. Though his work was not entirely original, it was certainly groundbreaking. Dr. Jan Peterson had previously developed a typology for Viking swords consisting of twenty-six categories. Peterson's typology was simplified by Dr. R.E.M. Wheeler in short order to only sevencategories (Type I-VII). This simplified typology was then slightly expanded by Oakeshott by the addition of two transitional types into its current nine categories (Type I-IX). From this basis, Oakeshott began work on his own thirteen-category typology of the medieval sword ranging from Type X to Type XXII.

What made Oakeshott's typology unique was that he was one of the first people either within or outside of Academia to seriously and systematically consider the shape and function of the blades of European Medieval swords as well as the hilt, which had been the primary criteria of previous scholars. His typology traced the functional evolution of European swords over a period of five centuries, starting with the late Iron Age Type X, and took into consideration many factors: the shape of blades in cross section, profile taper, fullering, whether blades were stiff and pointed for thrusting or broad and flexible for cutting and etc. This was a breakthrough. Oakeshott's books also dispelled many popular cliches about Western swords being heavy and clumsy, he listed the weights and measurements of many swords in his collection which have become the basis for further academic work as well as templates for the creation of high quality modern replicas.

• The Archeology of Weapons: Arms and Armour from Prehistory to the Age of Chivalry Boydell Press, 1960. ISBN 0-486-29288-6
• The Sword in the Age of Chivalry Boydell Press, 1964. ISBN 0-85115-715-7
• Records of the Medieval Sword Boydell Press, 1991. ISBN 0-85115-566-9
• European Weapons and Armour: From the Renaissance to the Industrial Revolution Boydell Press, 2000. ISBN 0-85115-789-0
• Sword in Hand Arms & Armor, Inc. 2000. ISBN 0-9714379-0-4
• A Knight and His Weapons Dufour Editions 1964, 1997. ISBN 0-8023-1299-3
• A Knight and His Armor Dufour Editions —, 1999. ISBN 0-8023-1329-9
• A Knight and His Horse Dufour Editions 1962, 1995. ISBN 0-8023-1297-7
• A Knight in Battle Dufour Editions —, 1998. ISBN 0-8023-1322-1
• A Knight and His Castle Dufour Editions 1965, 1996. ISBN 0-8023-1294-2
• Swords of the Viking Age Boydell Press 2002. ISBN 0-8023-1294-2
• The Sword in Anglo-Saxon England Boydell & Brewer 1962. ISBN 0-85115-355-0

http://uk.youtube.com/watch?v=Pe3NhaR-fSw