Some feedback on this based on my reading around and my engagement with a solicitor specialising in trademark agent work.
Firstly, he strongly warns against confusion of registering a trademark and registering a company name or a business name used by its owning company. AAM forums has been through this discussion before so I won't labour it. Suffice it to say that company names belong exclusively to you, business names only if they are trademarked and success in getting a business name mark (i.e. stylised business name with or without a logo) straight off, as opposed to getting it after years of trading and establishing a reputation and public association, precludes you selecting anything generic in text description, e.g. Irish Footwear, or graphically, e.g. an orange circle. Referring to my initial hypothetical example of Woulfe Footwear: this should be okay and receive an Irish trademark if no other Woulfe Footwear exists in Ireland prior to application and sufficient graphical distinctiveness is present.
As to any extraction of the stylised "W" graphic from the trademarked "Woulfe Footwear" wordmark, Mr Woulfe would not have got an Irish trademark for Wolfe Footwear in the first place if there wasn't something distinctive about his design and the stylised "W" would be an integral part of that. So the use of the stylised "W" on boxes would be okay provided that part of the logo was itself distinctive enough among other stylised "W"s already trademarked.