Button Boots Through Time: Heels, Toes and Flys, Oh My

Hello lovelies, and Happy New Year from American Duchess! In our last blog post of 2023, we explored ladies’ Victorian/Edwardian lace-up boots and spring heels. As we are going into our twelfth (!!!) year of producing functioning button boots, we thought it most appropriate to make our 2024 blog debut with a topic near and dear to our hearts: button boots, and the variety of shapes and styles they could be found in.

Button boots were preceded by buttoning gaiters, which were worn over one’s shoes, in the early 19th century- think c. 1805-1810. By the late 18-teens, gaiters and shoes had evolved into more convenient all-in-one shoe and gaiter combinations. Gaiters and spats with buttons would continue to be worn all the way through the early 20th century for a variety of uses. However, all-leather boots gained popularity through the 1840s; they were drier and warmer than cloth and leather combinations.

This 1850s/1860s boot is particularly interesting because it features a button fly (with 14 buttons!) AND an elastic gore.

Boot trends in the 1830s-1850s were all about side closures. Front-lacing was not at the height of fashion, and front-lacing boots were considered common (for more info about this, check out our blog post One Boot to Rule Them All). Congress boots with elastic gores on the sides, side-lacing boots like Keckley, and towards the end of this time period, side-button boots, were much more en vogue.

Square toes, scalloped flys, and lower heels are generally a good indication that button boots are from the very late 1850s to the early 1870s. For example, we replicated these features in our Renoir button boots.

Pink leather boots, 1868, from the LACMA collection. Note the lovely scalloped fly and scalloped top!
White leather boots from the Met Collection, c. 1863.

These leather boots from the Metropolitan museum have a curvy knock-on heel- in addition to the scalloped fly and soft, square toe, this heel shape helps date this boot to the 1860s.

We actually have quite a similar boot in our collection, which we used as the basis for our very first iteration of Renoir. Check out how the toe is super square- this strongly suggests that this boot is from 1865-1870.

Button boots c. 1867, from the collection at the Met Museum.

Another gorgeous pair from the Metropolitan Museum! These textile and leather boots can be dated to the late 1860s by the heel height and shape, scalloped fly, shaped top, and shaft height.

Boots with scalloped flys could be found through the 1890s, but their sweet spot for popularity was really centered in the very late 1850s through 1870s. Straight flys, which were found alongside scalloped flys throughout the mid-Victorian era, were the norm by the 1880s.

We designed our Tavistock Boots to reflect this fashion, with a straight fly and more pointed toe.

In the later decades of the 19th century, the toes on button boots changed shape. The previously popular square toe gave way for a more pointed toe through the 1880s, and by the 1890s, one could find button boots with very elongated, exaggerated pointed toes.

Heel shapes also began to change. More curvaceous French heels replaced kidney knock-on heels as the popular choice for button boots, and higher heels became more in style as well.

These button boots from the collection at the Metropolitan Museum are an excellent example of styles transitioning. They have a scalloped fly, but the toe is more tapered than a typical 1860s square-toed boot, and the heel is a higher, curvaceous French heel. They date to c. 1883.

This page from the spring 1896 Sears Roebuck catalogue demonstrates how the trends we’re discussing are just that- trends. You can see here a variety of heel heights and shapes, button boots and lace-ups, scalloped flys and straight flys, and congress boots. Note how very popular the pointed toe was!

These gorgeous white leather boots are super 1890s. The 2″ high spool heels, taller shaft with 13 buttons, straight fly, and pointed toe were all on trend for that decade.

These boots from the Metropolitan Museum date to right around the turn of the century. The straight fly, French heel, and pointed toe all suggest they are from the late Victorian/early Edwardian era. The foxing and toe cap indicate that they are probably from the later end of that time period, c. 1900-1910.

Remember how we discussed gaiters and cloth-and-leather boots from the earlier 19th century? Well, as fashion is wont to do, this sort of style came back into fashion in the 1890s with cloth-top button boots (like our Manhattan Boots). With the popularity of menswear-inspired fashions for ladies and the rise of sporting culture, spats-inspired cloth-topped button boots came into fashion in a big way around the end of the Victorian era and persisted through the 19-teens. We have another blog post specifically about the history of cloth-top button boots, which you can read here.

This photo from the V&A Museum shows a men’s cloth-top button boot (in the background) and a woman’s cloth-top button boot (in the foreground), c. 1890-1900. The toe cap also points to the late Victorian/Early Edwardian era.

These typical cloth-top button boots from the Manchester Art Gallery date to around 1900-1910.

If you see a button boot with a bulbous toe, like these from the Metropolitan Museum, you can bet it’s from the swan song era of button boots, around 1910-1920. Inspired by menswear, a high and knobbly toe is distinctive to this time period.

This two-tone leather pair of Bally brand boots from the Manchester Art Gallery is from around 1900-1910- the rounded, but not totally bulbous, toe is pointing towards this toe trend.

Oh- and we would be remised if we didn’t mention the fancier side of the button boot universe! In addition to daywear boots, the late Victorian/Edwardian era saw the rise of very sexy, evening-wear button boots. The 1890s was a particularly rich decade for high French heels, vivid colors, intricate cutouts, and major charisma for boots.

These beauties from the 1890s are the inspiration behind our Colette boots.

Some more gorgeous 1890s pair of cutout boots from the collection at LACMA. See the little bows? Swoon!

Be still my heart- beads. These boots are likely dated to a bit later in the Edwardian period, closer to 1910 or the 19-teens.

Regardless of what time period and trends you most desire in a pair of functional button boots, we have something to fit! If scalloped flys make your heart flutter, go for Renoir. If you love pointed toes and a straight fly, Tavistock is the boot for you. If you love the cloth-topped styles of the late Victorian/early Edwardian era, choose Manhattan. Don’t forget your button hook!


  • bahnwärterin

    January 24, 2024 at 10:04 AM

    hello duchess!
    i was reading your blog regularly ages ago and then lost it somehow…….
    today i found you again while searching for inspiration how to wear a high waisted, vintage pair of wool/loden trousers…..
    you did not disappoint 😀
    i´m very impressed by the boots you´ve designed – they all look gorgeous!

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