I’m not so familiar with the chukkas, but they seem to split pretty evenly into ones that are pointier (eg Tetbury) and rounder shapes (eg the Chiltern). I’d stick to the rounder end probably

Sorry, I was still referring to the chukka boots. I see four models the Chukka, Chiltern, Tetbury and Upton.

It depends on the style – usually Boston or Harvard, but that is a slightly more casual, preppy style. Otherwise something longer like Sydney

Cheers! Which C&J dark brown suede model do you prefer?

No problem.

In that case I’d look at Crockett & Jones, or one of the Spanish makers like Carmina

In regard to Chukkas, where would you suggest looking? Edward Green is far too much for my wallet, something in the £450 and under range ideally.

Thanks in advance.

Well, I’d pick the Piccadilly, but I wear them with tailoring a lot too. For your lifestyle I’d say probably the Boston would be the best choice…

Looking to replace my old brown suede loafers with something new and better quality (they have also fallen apart).

I am thinking of going either with the EG Piccadilly or C&J Boston. Based on my lifestyle (mainly straight denim / straight rubato chinos) – I feel the C&J would be more versatile… but I do have the C&D Harvard in Dark Brown Cordovan which makes the Piccadilly more attractive.

If you could only pick one brown suede penny loafer, which would you pick?

Well, it would of course depend on your lifestyle and work, to the same extent. Eg for me it would be:
– Black calf or grain
– Dark brown suede
– Col8 cordovan
– Tobacco suede
– Dark brown calf

Curious if this is instead the 5 loafers capsule wardrobe, what would the 5 be?