Jack Classic Gusset Boot

The Story:


Introducing the Jack Classic Gusset Boot. This wholecut Chelsea Gusset boot is made from one piece of locally tanned Victorian bovine leather. This thick yet supple leather makes for a durable and comfortable boot that will mould and age with the wearer. The leather is hand finished in house. The Classic collection offers you a choice of five classic colourways for the boot and two choices of sole material (leather and rubber), edge finish (raw, brown or black), size range and toe shapes (chisel or almond).

The Jack Classic Boot offers more options across the board than our Jack Original Boot:

TOE SHAPE: Choose between the Stanley (tapered toe) dress last or the Cambridge (almond toe) dress last

OUTSOLE: Choose leather or choose Starr rubber black

UPPER COLOUR: Choose between Saddle Tan, Whisky, Teak, Cocoa or Black

SIZING: Available from sizes 6-13 in two different width fittings (see size chart for width and toe shape availability). Stanley toe shape available in the narrow D fitting from size 6-13AU. Stanley toe shape only available in the wider E fitting from size 7-12.5AU. Cambridge toe shape available in the wider E fitting from size 6-13AU. Cambridge toe shape only available in the narrow D fitting from size 6, 7-12AU.

Please note that colours pictured will vary from hide to hide. We try to give as close a representation of each colour as possible. Cocoa is the darkest brown and is tanned a dark brown hue all the way through the leather. Teak is a milkier chocolate brown hue with some mottling to its colour and finish. Whisky is a very dark tan/reddy brown. Saddle tan is our lightest tan hue.

Please note all our current boots come with branded Wootten pull tabs.

Please note that this Classic Boot is part of our Made-To-Order footwear range. Lead times can be found in our footer below for leather goods and footwear.

Sole Types

Fitting Guide:

Made on our Cambridge (almond toe)  or Stanley (tapered) lasts for a dressier look.

Please refer to our ‘Size Guide’ below for information on the fittings of these two lasts. The Cambridge is an E fitting whilst the Stanley is a more narrow D fitting. Fitting stock is available in store to test the fit before purchase.

Size Guide

By Request:

If unsure about your size, please get in touch via email and we can help guide you. Please contact us with your measurements as per the FAQ Size Guide, and let us know what size you otherwise wear in dress boots (RMs), dress shoes, runners and other brands (please double check the size region and whether you're quoting in AU, US or EU so as to avoid confusion).

Fitting Availability

Samples available to try on for sizing at our Ballarat store. From size 6 to 13 in Cambridge and Stanley toe shapes.


Boot Size:

Toe Shape:

Width Fitting:

Sole Options:

Edge Finish:


Total (per item):