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Pocket slits in the skirts were not uncommon, as old-fashioned pockets were often worn under the habit (as riding made carrying a reticule difficult). In Figures 2 and 8 you can see the pocket holes which have been decorated to match the rest of the habit. The habit skirt had a train that ensured the legs were completely (and modestly) covered when riding side saddle. The jacket and skirt were made of sturdy fabrics, most often wool, and most often in either blue or green.

Figure 1
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Lady's Monthly Museum
July 1799
"Fashionable Riding Habits for July 1799"
Magazine text:
"Round beaver close cap, and feather in front, with gold chain-band round the crown. Gold band or muslin cravat round the neck. Blue, green, or corbeau jacket and petticoat, with black velvet collar, and double rows of Nelson's Ball, gilt buttons, fine tan leather gloves; half-boots of black Spanish or Morocco leather; a small quantity of hair appearing at the cap."
As with many prints in the early years of the Lady's Monthly Museum, the print depicts the same costume from two differnt angles and in two differnt colors. The description refers to both habits shown.
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Under the jacket, the habit shirt was generally made of muslin or cambric. They often followed the style of men's shirts, with high standing collars and a ruffled front. The shirt was tied beneath the bosom. Long sleeves might have lace cuffs to show beneath the jacket sleeves, as seen in Figure 7. The shirt might also be sleeveless. That style was sometimes called a chemisette and was worn to "fill in" the bodice of a day dress. A cravat was sometimes tied around the high collar, as seen in Figures 5, 6, and 8. The shirt became more frilly and feminine in the second decade of the 19th century, and ruffed collars were common, as seen in Figures 4 and 7. Figure 5 shows a combination of ruff and standing collar, with a blue cravat.
The habits of the first years of the 19th century still retained a tailored, masculine style, often adopting a military look (incorporating piping, braid, epaulettes, etc). Ornamentation increased over the years, just as it did for other types of women's fashion. This is clearly seen in the change from the plain cuffs on jackets to the embroidered cuffs of Figure 4, to the elaborate cuffs of the fabulous Glengary Habit in Figure 8. Hats continued to pay homage to male costume, as in the simple top hats shown in Figures 5 and 6, but just as often added a decidedly feminine plume or other ornament.
La Belle Assemblée
March 1807
"A French Lady on Horseback in the fashionable stile of riding in the Long Champs d'Elisée at Paris. Engraven from an original drawing taken on the spot for La Belle Assemblée or Bell's Court & Fashionable Magazine for March 1807."
Not to put too fine a point on it, but this print appeared earlier in the French magazine le Journal des Dames et des Mode, so the original drawing was not "taken on the spot" for LBA, but was engraved for LBA from the other publication's original drawing. This is one of the rare instances of a woman shown on horseback in a fashion plate. Note how the feet are completely covered by the train.
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Figure 2
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Note that in each of the fashion prints shown, the lady carries a riding crop. This prop was likely a convention used to easily identify a costume as a riding habit, since similar styles were used for carriage and traveling costumes. As a matter of fact, riding habits sometimes doubled as traveling costumes, as the sturdy fabric held up well over the dusty roads. The magazine commentary accompanying Figure 4 says the habit can be "happily adapted for travelling." It is possible that a different skirt, without the long train, would be substituted for a long carriage ride.
Some of the fashion prints identify the maker of the habit, and in almost every case it is a female dress-maker, such as the ubiquitous Mrs. Bell. It is likely that as riding habits became more feminine and more elaborately ornamented that the male tailor no longer seemed the appropriate designer. Since female dress-makers had been creating short, close-fitting spencer jackets for some years, it must not have been that great a leap to create a riding habit. However, male tailors still offered their services to ladies who wanted habits, as evidenced in various advertisements in the ladies' magazines of the day. Mr. G. Fox advertised in an 1817 issue of La Belle Assemblée: "Those Ladies who are very nice in their Dress are acquainted, that he employs particular workmen, who have for years constantly made up nothing but Woolen Pelisses and Habits, and therefore do form them into the most becoming and fashionable shapes, and much superior to any dress-maker." Sounds to me like a disgruntled man who did not appreciate women doing what had long been considered a man's job.
Click on any print to see a larger version

Figure 3
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Ackermann's Repository
December 1811
"Riding Habit "
Though this habit shows the narrowing of the silhouette seen in other garments of the day, it would not have been a slender skirt. There would be voluminous folds to allow for sitting upon a horse.
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Figure 4
La Belle Assemblée
October 1815
"Ladies Riding Habit"
Magazine Text:
"We are indebted this month to the fertile imagination of Mrs. Bell for a most elegant and useful novelty -- we mean the riding habit which she has just introduced. Habits have, ever since they were first brought into fashion, been considered as decidedly calculated to give even the most delicate female a masculine appearance, and the wits of our grandmothers' days were unmercifully severe on the waistcoat, cravat, and man's hat which were then the indispensible appendages to a habit; nor has the modern style of habit making, though less masculine, been more becoming. In the one now before us we are presented with an elegant and feminine dress, which is at once happily adapted for travelling and calculated to display to advantage the fine proportions of an elegant form, while a strikingly tasteful hat adds an air of smartness, without taking from the delicacy of a handsome face.
"The habit from which our print is designed was composed of the finest pelisse cloth, the body is formed in a most novel style, and the front and cuffs embroidered with much taste and originality; a very rich lace ruff of a new and peculiarly becoming form completes the habit. The hat is composed of moss silk, and ornamented with feathers to correspond; gloves and half-boots also to correspond. The tout ensemble of this dress is striking and tasteful beyond what our descriptive powers can portray, and we have no doubt that its striking utility as well as elegance will very soon render it a general favorite. At present it is adopted by some of the most distinguished fashionables of the haut ton."
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Figure 5
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La Belle Assemblée
June 1816
"Riding Dress, Invented by Mrs Bell"
Magazine text:
"Of fine blue Merino cloth, embroidered and ornamented round the bust and cuffs in a novel and unique style. This new equestrian costume, by fastening on the back of the shoulder, preserves all the contour of the form, which habits, in general, are apt to destroy. A full double ruff of fine Vandyke lace is separated from the shirt collar by a Chinese silk handkerchief of blue and white. Small round hat of fine beaver or of moss silk. Half boots of blue kid; with Limerick gloves worked and seamed with blue."
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La Belle Assemblée
July 1817
"Equestrian Costume, Invented by Mrs. Bell"
Magazine text:
"Habit of fine Merino cloth, of the Florentia blue colour, finished about the bust and cuffs with Peruvian trimmings. Blue military cap. ornamented with plumes of feathers and rich silk cordons. Ruff of fine Mechlin lace. The hair arranged in the Grecian style. Blue kid half-boots, and lemon-coloured gloves."
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Figure 7
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Figure 8
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Ackermann's Repository
September 1817
"The Glengary Habit" invented by Miss M'Donald.
Magazine text:
"It is composed of the finest pale blue cloth, and richly ornamented with frogs and braiding to correspond. The front, which is braided on each side, fastens under the body of the habit, which slopes down on each side in a very novel style, and in such a manner as to define the figure to considerable advantage. The epaulettes and jacket are braided to correspond with the front., as is also the bottom of the sleeve, which is braided nearly half-way up the arm. The habit shirt is composed of cambric, with a high standing collar, trimmed with lace. The cravat is of soft muslin, richly worked at the ends and tied in a full bow, and there are narrow lace ruffles at the wrists. The headdress takes the form of the Glengary cap, composed of blue satin, and trimmed with plaited ribbon of various shades of blue, and a superb plume of feathers. Blue kid gloves are worn and half-boots."
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For more information on fashion prints, see these sources:
Alison Adburgham, Women in Print: Writing Women and Women's Magazine from the Restoration to the Accession of Victoria, George Allen and Unwin Ltd., 1972.
Irene Dancyger, A World of Women: An Illustrated Hisotry of Women's Magazines 1700-1970, Gill and Macmillan, 1978.
Madeleine Ginsburg, An Introduction to Fashion Illustration, Victoria & Albert Museum, 1980.
Vyvyan Holland, Hand Coloured Fashion Plates 1770-1899, Batsford, 1955.
Doris Langley Moore, Fashion Through Fashion Plates 1771-1970, Clarkson N. Potter, Inc., 1971.
Sacheverell Sitwell and Doris Langley Moore, Gallery of Fashion 1790-1822, Batsford, 1949.
Cynthia L. White, Women's Magazines 1693-1968, Michael Joseph, 1970.
Alison Adburgham, Women in Print: Writing Women and Women's Magazine from the Restoration to the Accession of Victoria, George Allen and Unwin Ltd., 1972.
For more information on riding habits, see these sources:
Jane Ashelford, The Art of Dress: Clothes and Society 1500-1914, NAtional Trust, 1996.
R. L. Shep, Federalist and Regency Costume: 1790-1819, Shep publications, 1998.
Norah Waugh, The Cut of Women's Clothes 1600-1930, Theatre Arts Books, 1968.
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