The brown suede shoes that Sean Connery wears with his hacking jacket and cavalry twill trousers in Goldfinger and Thunderball are something people often ask me about. Thy are two-eyelet derby shoes in what essentially looks like a short chukka. The soles are dark brown rubber. The suede uppers, rubber soles and thicker laces make these more casual—but also more versatile—shoes. They work well with informal country wear like in Bond’s case, but they could just as easily be at home with a pair of jeans. They have a slight edge of formality over chukka boots, which allows them to be dressed up a little more whilst at the same time they can still be relatively casual shoes.

John Lobb Ltd, who made some of Sean Connery’s shoes for the Bond films, may have made this shoe, though this is a fairly common type of shoe amongst English shoemakers. Lobb calls this style the Plain V-Front.
Daniel Craig wears very similar shoes with his grey linen suit in Casino Royale.
Matt,
Nice feature on the shoes. I have a pair very similar to these and like them very much. They go very well with chinos or jeans. Are the shoes that Daniel Craig wears with the Grey linen suit in Casino Royale similar to these?
Yes, the shoes in Casino Royale are very similar, and I meant to mention that here.
Alfred Sargent do two eyelet derbies in suede but not so much of a chukka. The William model with leather sole. Very nice indeed
Hi Ryan,
I am still unclear on the difference between derby shoes and chukka shoes. Are short chukka boots the same as derby shoes?
A chukka is a type of derby boot. A chukka is a specific type of boot, often in suede, and derby is the open lacing style. Connery’s shoe brings elements of the chukka boot to a shoe.
Right. Thanks for the info Matt!
I have seen these around recently at shops liken Bostonian and even a retro pair at Aldo, attractive to say the least, I agree completely with the above remark in regards to wearing them with chinos, classic and modern at the same time.
I think there is even a more accurate Alfred Sargent model, this special Pimlico order: http://www.nomanwalksalone.com/index.php/footwear/shoes/holborn-suede-pimlico-two-eyelet-derby-2151.html
As a matter of fact I find their design quite similar to the Lobb shoes Craig wore with his dinner jacket in Casino Royale, and obviously quite similar to Connery’s black derbies shoes too.
John Lobb has several two eyelet derby’s that look very much like the ones Sean Connery wears in Goldfinger:
1. Tiverton: http://www.barneys.com/on/demandware.store/Sites-BNY-Site/default/Product-Show?pid=501587446
2. Luffield (Can be MTO in brown suede. Just call up any John Lobb store in the USA): http://www.jamesbondlifestyle.com/product/john-lobb-luffield
and many more if you search the Internet
The Luffield is no long made.
True, its not currently on JL’s website but if you call up any John Lobb store (I recommend Costa Mesa, CA), they can do a MTO for you.
I did a bit of searching and I found some shoes similar to the ones described above.
http://www.sidmashburn.com/shop/footwear/chocolate-suede-sid-mashburn-two-eyelet-gibson.html
These ones look more like the ones in your illustration. They are quite expensive.
http://www.houseoffraser.co.uk/Roland+Cartier+Coastal+suede+gibson+lace+up/D426730,default,pd.html
These ones have the same two-eyelet design but the cut on the side looks different. I’m not sure how to describe it but it looks like the cut goes further back toward the heel. This one is significantly less expensive though.
Hi Matt,
Sorry for coming back to an old post but I have a question regarding these shoes. Connery wore them with his hacking jacket and Craig wore them with his linen suit. Now, is it considered appropriate to wear these suede shoes with a worsted wool suit? Not a charcoal suit, but a suit in light grey or cream?
Always feel free to revisit and old post. These shoes would be okay with a light-coloured worsted suit. But suede oxfords would be even better. I’d save the suede derbies for sports coats, linen suits and tweed suits.