English arms : gallery
Three of them Robert's, Sir Leonard's, and William's are evidently authentic. Most of the others, including the versions with gold borders, appear to be the results of transcription and printing errors.
Please note that these arms are not freely available to anyone of English descent who happens to be named Halliday or Holliday. Only the College of Arms in London can determine who, if anyone, has a rightful claim to any of them.
You'll find a broader overview, placing these arms and sources in context, here.
Robert's daughter and sole heiress Agnes married Robert Massingberd (d 1459). These arms appear as a quartering in the arms of Agnes's grandsons Sir Thomas Massingberd (d 1552) and Archdeacon Christopher Massingberd (d 1553), on their tombs in St Peter's church in Gunby and Lincoln Cathedral respectively. From this, we can deduce that they were Robert Halliday's arms, and that they date from the late 14th or early 15th century, if not earlier.
Listed in Edmondson's Complete Body of Heraldry (1780), Berry's Encyclopaedia Heraldica (1828) and Robson's British Herald (1830) as 'Halyday or Holyday'.
ECBH Vol 1, HBSB, PECF, RBH Vol 1
Unidentified Sable, three helmets within a bordure engrailed Argent.
These arms, captioned simply 'Stokes Chlr', are shown in a manuscript roll of English arms known as the Insignia Anglica, which appears to date from c1551. As 'chlr' is the abbreviation for 'chevalier', this Stokes was apparently a knight. The 2nd and 3rd quarters suggest that his mother, or an earlier female ancestor, was a Halliday heiress.
Who was he? There is no Stokes, or similar surname, in published lists of knights of that period and, according to Burke's General Armory (1884), the arms in the 1st and 4th quarters are those of Waffer, not Stokes.
Sir Leonard Holliday (d 1612) of London (originally of Gloucestershire)  Three helmets.  Sable, three helmets Argent garnished Or all within a bordure engrailed Argent. Crest : A demi-lion gardant Or supporting an anchor proper.
Sir Leonard evidently used two versions of the arms. Version , together with his initials, was stamped on the bindings of some books which he presented to St John's College, Oxford, in 1600. How he acquired the arms is unclear.
Version  was authorised by the Clarenceux King of Arms on 21 September 1605. Clarenceux confirmed these as Sir Leonard's arms, and granted him the crest to go with them.
Sir Leonard was a wealthy businessman and a director of the East India Company, and was about to serve a term as lord mayor of London. Might the gold trimming on the helmets have referred to his wealth, the lion ('leo' in Latin) to his name, and the anchor to maritime trade? We can but speculate.
Listed in Morgan's Sphere of Gentry (1661) and Mackenzie's Guillim's Display of Heraldry (1724); by Edmondson, Berry and Robson; and in Burke's General Armory (various editions).
As Sir Leonard's son died before him, the arms  and crest were inherited by his grandson John (b 1610). John recorded the arms and crest under his name at the heralds' visitation of Middlesex in 1664.
Sir Leonard's granddaughter Elizabeth (1608-31), who married John Jacob, had courtesy use of the arms but not the crest for her lifetime. The arms were depicted on a Jacob family monument in St Leonard's church, Bromley (Middlesex). Lyson's Environs of London (1795) gives the blazon as Sable, three helmets Argent within a bordure engrailed of the second, which is not quite correct as the helmets should be garnished in gold.
Ashbee's Survey of London (1900) gives the field of the arms on the monument as blue, the helmets as gold, and the bordure as silver, which is clearly wrong. Perhaps the monument had discoloured over time, or been repainted in the incorrect tinctures.
MGDH, MSG, RBH Vols 1 & 2, RGA Vol 1, UBAB
Alderman William Holliday (1566-1624) of London (originally of Gloucestershire) Sable, three helmets Argent, a bordure of the same Crest : A demi-lion Or armed and langued Gules supporting an anchor proper.
These arms were granted to William Holliday (or 'Hollidaie') by the Norroy King of Arms on 13 February 1624 (or 1623 by the Old Style calendar in use at the time). Clearly, they were based on his cousin Sir Leonard's arms. As William had no sons, his arms but not the crest were inherited by his daughters Anne (1602-57) and Margaret (1603-73).
Anne married Sir Henry Mildmay. Their children would have inherited William's arms as a quartering.
Margaret married Sir Edward Hungerford. They had no children, but nevertheless Margaret left an heraldic legacy. The arms were displayed at St Bartholomew's church in Corsham (1631) (Wiltshire), on a portrait of Margaret (1633), at Farleigh Hungerford Castle (Somerset), on the Hungerford Almshouses in Corsham (1668), on silver plate presented to the church at Kings Stanley (Gloucestershire) (1673), and on a monument in St Lawrence Jewry church in London (1687). The monument was destroyed in an air raid in World War II. Not all these displays are correct. Some confuse William's arms with Sir Leonard's.
The motto 'Quarta salutis' ("the fourth of salvation") appears on some of these displays of the arms. It's been interpreted as a reference to the Helmet of Salvation mentioned in the New Testament. The idea is that there are three helmets visible on the shield, and a fourth, unseen, helmet which is the Helmet of Salvation.
LIW, NLP, PHUF, RGA Vol 1, SCHNW, WPMH
Archdeacon Barten Holyday (1593-1661) of Oxford Sable, three helmets within a bordure engrailed Argent, a fleur de lis in fess Or for difference.
According to Mackenzie's Guillim's Display of Heraldry (1724), these were Barten Holyday's arms.
Did he really use them? He was Archdeacon of Oxford 1626-61, but yet he was not listed in the heralds' visitation of Oxford in 1634 as using these or any other arms. If he did use them, from whom did he inherit them?
Listed by Robson and in Burke's General Armory but without the fleur de lis.
'Hollyday (London)' Sable, three close helmets Argent garnished Or two and one.
These arms are listed by Edmondson (1780) as 'Hollyday (London)'. Both Berry (1828) and Robson (1830) list them (i) as 'Halyday (London)', (ii) as 'Holliday (London)' with a crest of a demi-pegasus, and (iii) as 'Holliday (London 1605)'.
According to the unofficially published edition of the Visitation of Middlesex (1820), these are the arms and crest recorded by John Holliday in 1664. However, the blazon is evidently incorrect. As John was Sir Leonard's grandson and heraldic heir, the bordure should be Argent.
Bluemantle Pursuivant's report on Halliday arms (1975) refers to the (official) visitation record held by the College of Arms, but does not mention any change in tincture. The change is very likely a printing error : 'ar' (for 'Argent') is easily misread as 'or'. The blazon of the crest too is muddled, as 'Or' should follow 'gardant', not 'anchor'.
'Holliday' Azure, a fess between three helmets Or. Crest : A grenade fired proper.
These arms are listed by Berry (1828) and Robson (1830), without further details. Both authors also list the arms under 'Coveley'.
Clearly there was some some confusion. Was a Holliday actually using these arms, or did Berry make a mistake, which was then copied by Robson? These arms were evidently not officially granted to any Halliday/Holliday.
'Halliday' Or, three saltires couped.
These arms are listed by Robson (1830), without further details. The blazon is incomplete : what colour are the saltires?
Where Robson found the blazon, and why he attributed these arms to Halliday, is unclear. Was any Halliday actually using them? They do not appear to have been officially granted to any Halliday.
Simon Welman Halliday (d 1842) of Brompton, Middlesex, and John Halliday of Chapel Cleeve, Somerset Sable, three helmets Argent garnished Or, within a bordure engrailed of the second [Halliday] quartering Or, on a bridge of three arches in fess Gules masoned Sable the streams transfluent proper, a fane Argent [Trowbridge]. Crest : A demi-lion Or holding an anchor Azure. Motto : Quarta saluti.
According to Burke's Commoners (1836), Landed Gentry (1847, 1852, 1875) and General Armory (1847 and 1884), these arms were borne by Simon Welman Halliday and, later, by John Halliday, as heads of the Wiltshire/ Somerset branch of the family. The Trowbridge quartering evidently represents their ancestress Mary, who was the daughter and heiress of Edmund Trowbridge.
These books state that the Halliday arms were granted in the time of King Edward IV (1461-83), but do not say to whom. This information probably came from Simon. However, the College of Arms has said that it has no record of any such grant.
The arms are actually Sir Leonard's, dating from 1605. The crest is actually William's crest (dating from 1624) with the anchor changed to blue. The motto is that used by William's daughter Margaret, with the final 's' missing (which changes the meaning). However, Simon and John were not descended from Sir Leonard or from William.
No Halliday appears to have been recorded in any of the visitations carried out in Wiltshire, Somerset and Gloucestershire between 1530 and 1682, as using these or any other arms. Might the arms perhaps have been adopted by John Halliday who married Mary Trowbridge in the early 1700s? Without Halliday arms to quarter with, their children would not have been able to inherit the Trowbridge arms.
There also exists a 19th(?)-century bookplate with the name 'James Holliday' and these quartered arms.
BLG 1875, BGA 1884, BPR, RBC
John Halliday of Rodborough, Gloucestershire According to Burke's Commoners (1836), he used the same arms as Simon Welman Halliday, but the lion in his crest was regardant, i.e. looking back over its shoulder. However, according to Burke's General Armory (1847 and 1884), the crest was the same as Simon's, i.e. the lion faced forward.
Which, if either, is correct? What claim did the Hallidays of Rodborough actually have to these arms? Was it also based on the supposed, but unproven, grant from the time of Edward IV?
This is according to Burke's General Armory (1884), which refers to the 1663 visitation of Middlesex. Evidently this is an incorrect transcription of the already muddled entry for John Holliday in the unofficial published version of the visitation record. Not only has the bordure again been given as 'Or' instead of 'Argent', but the word 'engrailed' has been omitted, which technically makes this a different coat of arms. The omission of 'Or' from the blazon of the lion also changes the crest.
'Edward Holliday' Sable, three helmets Argent, a bordure engrailed Or.
This blazon appears in Weaver's Visitations of the County of Somerset in the Years 1531 and 1573 (1885) as a footnote to the Richmound family tree. One of the Richmounds is shown as having married an unnamed daughter of one Edward Holliday. Weaver's edition of the visitation records is based on unofficial copies of copies of the originals.
As there's no entry under Holliday's own name, and Weaver refers to "Burke's Armoury" (sic), it appears that he added this blazon himself, and that it may not be in the original visitation record. However, it's not in Burke's General Armory either. It most closely resembles the dubious blazon in the published Visitation of Middlesex, without the gold garnishing on the helmets.
'Holladay, Virginia' Sable, three helmets Argent garnished Or, a border of the last. Crest : A demi-lion rampant resting the paws on an anchor Azure. Motto : Quarta salute
This is the blazon given in Crozier's General Armory (1904), which identifies the founder of the Virginia branch of the family as "Captain John Holladay, Spotsylvania County, 1702". He was John 'the Ranger' Holladay (c1676-1742).
Clearly, the blazon of the arms was taken from the incorrect 'Holliday (Bromley, co Middlesex)' entry in Burke's General Armory (1884), and the crest and motto from Burke's entry for 'Halliday (cos Wilts and Somerset)', with 'Or' omitted from the crest (which then makes the lion blue) and the second word of the motto misspelled (which changes the meaning).
According to Crozier, the arms were granted to Walter Halliday by King Edward IV in 1470. This appears to be an elaboration of the claim made in Burke's various books that the arms had been granted in the reign of (not by) Edward IV. However, as already noted, the College of Arms has no record of any such grant, and the story is thus unproven.
Do or did the Holladays of Virginia actually bear the arms in this form? If so, on what basis? For John 'the Ranger' to have had a claim to the correct version of these arms, he would have needed to be descended from Sir Leonard Holliday. Some published American pedigrees (and various family websites) do indeed make out that John's father Thomas was Sir Leonard's grandson or great-grandson. However, no such Thomas is listed in the Holliday pedigree recorded at the 1663-64 visitation of Middlesex.
James Holliday (1696-1747) of Readbourne, Maryland Sable, three helmets Or garnished Or within a bordure engrailed of the second.
According to Bolton's American Armory (1927), these arms are/were on James Holliday's gravestone.
Bolton gives Ridgely's Historic Graves of Maryland as his source, but while that book describes the grave it doesn't mention the arms. The book does however mention that James's brother Leonard Holliday's gravestone bore the "family coat of arms".
The blazon is surely wrong. "Or garnished Or" is redundant, and the helmets and bordure are probably supposed to be Argent. The abbreviation 'ar' is easily misread as 'or'. If so, these would be Sir Leonard's arms.
It appears that the family did indeed use Sir Leonard's arms. But were James and Leonard really descended from Sir Leonard? Some published American pedigrees (and various family websites) make out that their father Thomas was Sir Leonard's grandson or great-grandson. However, no such Thomas is listed in the Holliday pedigree recorded at the 1663-64 visitation of Middlesex.