If you are in doubt, use the unbound form which is correct in both cases:

l'uomo con il cane = the man with the dog (l'uomo col cane would be the form used in spoken language) la donna con la borsa = the woman with the hand-bag (la donna colla borsa would be correct in spoken language)

5.3 POSSESSIVE ADJECTIVES AND PRONOUNS

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In Italian, possessive adjectives and possessive pronouns are exactly the same. They correspond to the English ones, but while in English possession is expressed by two different forms, one as adjective (my, your, his, her, etc.) and one as pronoun (mine, yours, etc.), Italian has only one form, used in both cases.

mio	my - mine
tuo	your - yours
suo	his/her/its - hers
nostro	our - ours
vostro	your - yours (plural)
loro	their - theirs

But as any other Italian adjective and pronoun, they are gender- and number-sensitive (except one): feminine and plural inflections are almost the same ones used for common adjectives:

masculine singular	feminine singular	masculine plural	feminine plural
mio	mia	miei (irregular)	mie
tuo	tua	tuoi (irregular)	tue
suo	sua	suoi (irregular)	sue
nostro	nostra	nostri	nostre
vostro	vostra	vostri	vostre
loro	loro	loro	loro

Possessive adjectives and pronouns used as subjects

An important difference with English is that either used alone (as pronouns) or followed by a noun (used as adjectives), they always need an article (definite or indefinite), while in English always rejects articles before a possessive adjective or pronoun.

la mia automobile è veloce = my car is fast (here my acts as an adjective for the noun car) la loro è lenta = theirs is slow (here theirs is a pronoun, meaning their car, not mentioned) il suo gatto prese un topo = his cat caught a mouse anche il tuo prese un topo = also yours caught a mouse il vostro albero è alto = your (plur.) tree is tall il loro è basso = theirs is short un tuo parente = a relative of yours (or one of your relatives) uno mio = one of mine

(this last example also recalls the rule for indefinite articles used as pronouns, explained in paragraph 2.4). Only when the possessed noun is a specific family relative the article is dropped, as in English:

mio padre è alto (not "il mio padre") = my father is tall mia madre è giovane (not "la mia madre") = my mother is young mio fratello è pigro (not "il mio fratello") = my brother is lazy

This will be explained again further down in the page, in a more detailed way, with further examples. Another important difference is that while in English the gender of the possessive pronoun matches the possessor, in Italian it matches the possessed subject:

mio padre ha una bicicletta = my father has a bycicle la sua bicicletta (sua matches bicicletta, feminine) = his bycicle (his matches father, masculine) mia madre ha un cane = my mother has a dog il suo cane (suo matches cane, masculine)= her dog (her matches mother, feminine)

Number too must match the possessed subjects (English possessive pronouns do not have a plural):

mio padre ha due biciclette = my father has two bycicles le sue bicicletta (sue matches biciclette, feminine plural) mia madre ha tre cane = my mother has three dogs i suoi cani (suoi matches cani, masculine plural)

The article too matches the possessed subject (noun) for gender and number, but it matches the possessive pronoun for phonetics. If this seems difficult, focus this sample sentence:

la mia automobile è veloce = my car is fast

la is a feminine singular article, since automobile is a feminine singular noun; mia is a feminine singular possessive pronoun, for the same noun. Had the pronoun mia not been there, the sentence would have read:

l'automobile = the car

where the article la would have been shortened in l', phonetically matching automobile. But in the previous sentence, the the word next to the article is not the noun but mia, which has to be phonetically matched. These are more sentences with the same situation.

l'occhio	the eye		il mio occhio	my eye
la casa	the house		la tua casa	your house (singular)
lo studio	the study		il loro studio	their study
un'amica	a friend (feminine)		una mia amica	a friend of mine (feminine)

The definite article is omitted only when nouns indicate a family relationship:

padre = father ; madre = mother ; fratello = brother ; sorella = sister ; marito = husband ; moglie = wife ; figlio = son ; figlia = daughter ; zio = uncle ; zia = aunt ; nonno = grand-father ; nonna = grand-mother ; nipote (both sexes) = nephew / niece / grand-son / grand-daughter ; suocero = father-in-law ; suocera = mother -in-law ; genero = son-in-law ; nuora = daughter-in-law .

Therefore:

il mio amico = my friend (note the use of the article il) .......BUT mio padre = my father (without an article) la madre del mio amico = my friend's mother (with compound preposition del = di + il) .......BUT l'amico di mia madre = my mother's friend (with simple preposition di) regalerò un libro al mio amico = I shall give a book to my friend (preposition al = a + il) .......BUT regalerò un libro a mio zio = I shall give a book to my uncle (with simple preposition a)

If the noun is plural, it requires an article in any case:

mia sorella = my sister (without an article) .......BUT le mie sorelle = my sisters (with an article) la casa di mio nonno = my grandfather's home (with simple preposition di) .......BUT la casa dei miei nonni = my grandparents's home (with compound preposition dei) comprerò un regalo per tuo genero = I will buy a gift for your son-in-law (without an article) .......BUT comprerò un regalo per i tuoi generi = I will buy a gift for your sons-in-law (with an article) (notice that preposition per does not form compounds with articles)

Indefinite articles, instead, are always used, also for relatives:

mio zio = my uncle un mio zio = an uncle of mine (or one of my uncles), with an article mia nonna = my grand-mother una mia nonna = one of my grand-mothers, with an article

Notice that, as for most other nouns, when a family relation name is plural, the masculine form may refer either to masculine gender only or to both genders (meaning masculine and feminine together, i.e. uncles and aunts, grand-father and grand-mother, etc.), while feminine plural only refers to feminine relatives. Instead, when nouns describing different sexes have a different root, both nouns are actually mentioned:

zio	uncle	zia	aunt
zii	uncles or uncles and aunts	zie	aunts (only)
nonno	grand-father	nonna	grand-mother
nonni	grand-fathers or grand-parents	nonne	grand-mothers (only)
	...BUT
fratello	brother	sorella	sister
fratelli e sorelle	brothers and sisters
genero	son-in-law	nuora	daughter-in-law
generi e nuore	sons- and daughters-in-law