John Lobb City II Oxford vs John Lobb William Double Monk

John Lobb City II Oxford vs John Lobb William Double Monk: which one should you buy?

Quick answer

Buy the John Lobb City II Oxford if you want the reference formal oxford. Buy the John Lobb William Double Monk instead if you want an iconic monk.

By Opulique Editorial Team Updated November 6, 2026 1 min read

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Buy

John Lobb City II Oxford

Best for Benchmark oxford

Typically $1,795–$2,100

Check Price on Amazon Paid link

Buy

John Lobb William Double Monk

Best for Double monk icon

Typically $1,900–$2,200

Check Price on Amazon Paid link

Quick comparison

Feature	John Lobb City II Oxford	John Lobb William Double Monk
Verdict	Buy	Buy
Typical price	$1,795–$2,100	$1,900–$2,200
Best for	Benchmark oxford	Double monk icon
Key feature	Classic cap-toe oxford, Goodyear welted in Northampton	William double monk
Material	Box calf	Calf leather
Sole	Leather, Goodyear welted	Leather, Goodyear welted
Fit	True to size	True to size
Made in	England	England
Where to buy	Check Price Paid link	Check Price Paid link

Main differences

Material

John Lobb City II Oxford: Box calf; John Lobb William Double Monk: Calf leather.

Sole

John Lobb City II Oxford: Leather, Goodyear welted; John Lobb William Double Monk: Leather, Goodyear welted.

Fit

John Lobb City II Oxford: True to size; John Lobb William Double Monk: True to size.

Made in

John Lobb City II Oxford: England; John Lobb William Double Monk: England.

Why buy it

John Lobb City II Oxford: classic cap-toe oxford, Goodyear welted in Northampton; John Lobb William Double Monk: william double monk.

Made for

John Lobb City II Oxford: benchmark oxford; John Lobb William Double Monk: double monk icon.

Usual price

John Lobb City II Oxford: $1,795–$2,100; John Lobb William Double Monk: $1,900–$2,200.

Which should you choose?

Choose the John Lobb City II Oxford if you

you want the reference formal oxford
value superb craft

Check Price Paid link

Choose the John Lobb William Double Monk if you

you want an iconic monk
value superb

Check Price Paid link

If neither feels right

Neither is the only answer. See every piece we would buy (and the ones we would skip) in our list of the best men’s dress shoes.

Not sure about either? Consider these

Edward Green · Men’s dress shoes

Edward Green Chelsea 202

Buy it if you want handmade English elegance.

Verdict: Buy
Best for: Connoisseur pick
Typical price: $1,500–$1,700

Pros

Excellent finishing
Resoleable

Cons

Pricey

Check Price on Amazon Paid linkRead our review

Gaziano & Girling · Men’s dress shoes

Gaziano & Girling St James II

Buy it if you want near-bespoke ready-to-wear.

Verdict: Buy
Best for: Bespoke-level RTW
Typical price: $1,900–$2,300

Pros

Exceptional finishing
Elegant

Cons

Expensive

Check Price on Amazon Paid linkRead our review

Frequently asked questions

John Lobb City II Oxford or John Lobb William Double Monk: which should I buy?

Buy the John Lobb City II Oxford if you want the reference formal oxford. Buy the John Lobb William Double Monk instead if you want an iconic monk.

Is the price difference worth it?

The John Lobb City II Oxford usually costs $1,795–$2,100 and the John Lobb William Double Monk $1,900–$2,200. Pay more only if the differences above matter to you.

Opulique Editorial Team

Part of the Opulique research team. We compare specifications, documentation and real-world trade-offs so you can decide faster.

How we research products Editorial policy

John Lobb City II Oxford or John Lobb William Double Monk: the full reasoning

John Lobb City II Oxford or John Lobb William Double Monk? Both are strong men’s dress shoes, which is exactly why the choice is hard. The short version first: buy the John Lobb City II Oxford if you want the reference formal oxford, and buy the John Lobb William Double Monk if you want an iconic monk. The rest of this page explains why, with usual US prices.

Where they differ

The John Lobb City II Oxford wins on classic cap-toe oxford, Goodyear welted in Northampton. The John Lobb William Double Monk answers with william double monk. Material: Box calf on the John Lobb City II Oxford, Calf leather on the John Lobb William Double Monk. Sole: Leather, Goodyear welted on the John Lobb City II Oxford, Leather, Goodyear welted on the John Lobb William Double Monk. Fit: True to size on the John Lobb City II Oxford, True to size on the John Lobb William Double Monk. Made in: England on the John Lobb City II Oxford, England on the John Lobb William Double Monk.

Reasons to buy the John Lobb City II Oxford

Superb craft, Resoleable, Timeless. What to accept: expensive. Usual price: $1,795–$2,100. Our verdict: buy. Read the full John Lobb City II Oxford review.

Reasons to buy the John Lobb William Double Monk

Superb. What to accept: pricey. Usual price: $1,900–$2,200. Our verdict: buy. Read the full John Lobb William Double Monk review.

Neither one?

Our list of the best men’s dress shoes has every other piece with its own call. Construction: Goodyear-welted and hand-welted shoes can be resoled many times; Blake-stitched shoes are sleeker but resole fewer times.

Also consider the Edward Green Chelsea 202 ($1,500–$1,700): cap-toe oxford on the 202 last. Buy it if you want handmade English elegance.

Also consider the Gaziano & Girling St James II ($1,900–$2,300): sharp chiselled toe oxford. Buy it if you want near-bespoke ready-to-wear.

Buyer tip

Fit shoes in the afternoon, when feet are largest, and wear them with the socks you will use. Shoe trees in cedar double the life of good shoes.

Buying in Europe: Italian and French sizes are used on most designer shoes, and they differ from US sizes by brand. Check the house’s own size chart, and remember that many Italian brands run about half a size small.

Luxury prices move in a different rhythm from everyday shopping. The great houses (Chanel, Hermès, Louis Vuitton, Dior, Rolex) raise prices once or twice a year, often in January and in spring, and almost never discount their icons. Seasonal pieces, colors and many shoes, coats and knitwear drop 30–50% in the end-of-season sales in January and from late June. Watches from brands such as Omega, TAG Heuer, Longines and Breitling, and most fragrance, see the best prices around Prime Day and Black Friday. Judge any deal against the usual price we show.