How to say his shoes were so old that his toes were sticking out of them. in Japanese

1)彼の彼の(kano) (adj-pn) that靴(kutsu) (n) shoes/footwearは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sighとてもとても(totemo) (adv) very/awfully/exceedingly/ at all/by no means/simply古(ko) (n) antiquity/ancient timesか(ka) (prt) indicates question/indicates choice, doubt, etc.ったno dictionary result, likely a conjigated verb(prt) indicates possessive/nominalizes verbs and adjectives/substitutes for "ga" in subordinate phrases/indicates a confident conclusion/ indicates emotional emphasis/indicates questionで(de) (prt) indicates location of action/at/in/indicates time of action/indicates means of action/cause of effect/by/and then/so/indicates continuing action/ indicates certainty, emphasis, etc.足(ashi) (n) foot/leg/gait/pace/bottom structural component of a kanji/means of transportation/money/coinの(no) (prt) indicates possessive/nominalizes verbs and adjectives/substitutes for "ga" in subordinate phrases/indicates a confident conclusion/ indicates emotional emphasis/indicates question指(yubi) (n) finger/toe/digitが(ga) (prt) indicates sentence subject/indicates possessive/but/however/still/and靴(kutsu) (n) shoes/footwearか(ka) (prt) indicates question/indicates choice, doubt, etc.らはみno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb出てno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbいたいた(ita) (int) ouch/ow。(。) Japanese period "."    
kano kutsu hatotemo furuka ttanode ashi no yubi ga kutsu karahami dete ita 。
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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2)彼の彼の(kano) (adj-pn) that靴(kutsu) (n) shoes/footwearは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sighとてもとても(totemo) (adv) very/awfully/exceedingly/ at all/by no means/simply古い古い(furui) (adj-i) old/aged/ancient/antiquated/stale/threadbare/outmoded/obsolete articleのでので(node) (prt) that being the case/because of .../the reason is ..../given that...足(ashi) (n) foot/leg/gait/pace/bottom structural component of a kanji/means of transportation/money/coinの(no) (prt) indicates possessive/nominalizes verbs and adjectives/substitutes for "ga" in subordinate phrases/indicates a confident conclusion/ indicates emotional emphasis/indicates question先(saki) (n,adj-no,n-suf,pref) previous/prior/former/some time ago/preceding/point/tip/end/nozzle/head/front/ahead/the other side/the future/hereafter/destination/the other partyが(ga) (prt) indicates sentence subject/indicates possessive/but/however/still/and出てno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbいたいた(ita) (int) ouch/ow。(。) Japanese period "."    
kano kutsu hatotemo furui node ashi no sakiga dete ita 。
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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