I agree with you that oyster bands are more casual/sporty and jubilee more formal.
For me I have subs with oyster bracelets, so I would definitely get the DJ on jubilee and wear it when I was wearing a dress shirt and save my Subs for more casual wear.
Since it sounds like it is your only watch, I would base my decision on what you wear on a typical day. Are you normally in a pair of jeans? Then I would do oyster. Are you more often wearing a button down and slacks? Jubilee.
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