The school was founded in 1690 by a Royal Charter granted to the Worshipful Company of Haberdashers to establish a hospital for 20 boarders with £32,000 from the legacy of Robert Aske (equivalent to approximately £5M in 2019).

[2] The school relocated from its original site in Hoxton in 1874, eventually (1961) moving to 104 acres of green belt countryside in Elstree.

The house names in the preparatory and pre–preparatory schools represent the patron saints of the four countries of the United Kingdom – England, Scotland, Wales, and Northern Ireland.

[4] Designed by Robert Hooke, the almshouse comprised a chapel and, at its centre, the school, which provided education for 20 sons of poor freemen between the ages of nine and fifteen.

However, the chaplain, Thomas Wright, was then made master of Bunhill School and was thus unable to teach the boys at Aske's.

In 1697, therefore, John Pridie was appointed to teach the boys English, the catechism, and basic grammar at a salary of £40 a month.

Soon afterward, Pridie secured the right to admit pupils from paying parents, allowing him to increase the amount of money spent on the boys' education.

The school continued to cater to poor pupils, requiring any boy who inherited £100 or more to leave to make way for a less lucky individual.

[6] In 1818, the Charities Commission announced that the school's buildings required repairs that were too expensive for the company's allotted allowance.

The pupil body continued to comprise 20 poor sons of freedmen, and the curriculum consisted of the three Rs (reading, writing, and arithmetic) and the catechism.

The school replaced the former reading, writing, and arithmetic curriculum with Latin (having removed it in 1738), geography, grammar, accounting, and mathematics.

However, the company committee was satisfied that the significant improvement in the boys' education merited an increase in funding to £800 per year.

[9] In 1849, F. W. Mortimer, headmaster of the City of London School, criticized some of the textbooks used and the teaching of Latin, which he thought would be better replaced by French.

[10] In addition, he also recommended the introduction of geometry, business studies, trigonometry, mechanics, and natural philosophy to the curriculum.

The Bourne Building, home to the largest of the school's assembly halls, the library, along with several history, ICT and classics classrooms, is next to Aldenham House at the top of the Quadrangle.

The library was quite recently refurbished by the school and now contains various open and screened seating areas, as well as desktop and laptop computers.

[26] Behind the Aske Building, lies the recently constructed multi-purpose sports complex which was opened in 2016 and formally called the Medburn Centre, the complex boasts a 24.96m swimming pool, climbing wall, gymnasium, the Medburn Hall, squash courts, new changing rooms and Joe's Café in the lobby area.

The new buildings have state-of-the art classrooms and house the subjects: English, Theology and Philosophy and Modern Foreign Languages (in the Taylor) and Maths and Economics (in the Hinton).

The lower floor has 3 distinct DT workshops and 2 DT computer labs for classes to use and the upper floor has four studios for drawing, painting, printing, sculpture, digital design, textiles and ceramics on top of a dedicated Sixth Form studio and Art and Design library.

For the main academic subjects taken by boys to GCSE (which consist of mathematics, the sciences, and English), IGCSE papers are written.

The modern foreign languages department (MFL) also uses Cambridge International Examinations, apart from Spanish, which will start using the AQA specification from the 2024-25 year.

While the school places pupils in tutor groups, these are purely for pastoral purposes and are taught in mixed, or streamed, sets.

[44] Every year, students participate in a variety of interhouse events to contribute to the Crossman and Dunton shields, which are the main accolades awarded in the school.

Several ties are available for participation in extra-curricular activities and contributions to specific areas of school life (such as art).

The arms are blazoned: Barry wavy of six argent and azure on a bend gules a lion passant guardant Or, on a wreath argent and azure colours issuing from clouds two naked arms embowed holding a laurel wreath all proper, on either side a goat of India argent flecked gules and membered Or Motto: Serve and Obey These armorial bearings, including the crest of two arms holding a wreath, were granted to the Haberdashers' Company on 8 November 1570 by Robert Cooke, Clarenceux.

HabsMUN boasts a standalone website, the MyHabsMUN online portal, and a mobile app for delegates and advisors.

Pupils in year 10 have the option to partake in Outdoor Leadership instead of CCF, or SCS (school community service).

Students who do not participate in the Combined Cadet Force or Outdoor Leadership are required to do school community service (SCS) once a week.

In 2020, the former caretaker Justin Terry, 45, mixed cocaine with chemicals before pressing it inside his on-site lodge at Haberdashers' Aske's Boys' School, and was found by police with two kilo (2.2lb) blocks of the drug along with £37,000 cash hidden underneath his bed.

[54] As a result of discussion in 2021, Robert Aske's name was dropped from the boys' and girls' Haberdashers' Schools in Elstree, due to his previous links with the slave trade; although it was retained by their governing body.