To dip one's foot in oil/ to live luxuriously/ "to dip one's foot in oil
Metaphorically: to live in great wealth and comfort, with no financial worries.
("And of Asher he said: Blessed above sons is Asher; let him be favored by his brothers, and let him dip his foot in oil" - Deuteronomy 33:24 (Moses' blessing for the tribe of Asher), and likewise: "Our rabbis taught: 'And he dipped his foot in oil'—this is Asher's portion, for he draws oil like a spring" - Tractate Menachot 85b)
Translation
Expression (Hebrew)
טוֹבֵל בַּשֶּׁמֶן, טוֹבֵל בַּשֶּׁמֶן רַגְלוֹ
Definition (Hebrew)
בִּמְלִיצָה: חַי בְּעֹושֶׁר רַב. חַי חַיֵּי נַחַת לְלֹא דְּאָגוֹת כַּסְפִּיּוֹת.
(" וּלְאָשֵׁר אָמַר בָּרוּךְ מִבָּנִים אָשֵׁר יְהִי רְצוּי אֶחָיו וְטֹבֵל בַּשֶּׁמֶן רַגְלוֹ"- דְּבָרִים לג כַּד (בִּרְכַּת מֹשֶׁה לְשֵׁבֶט אֲשֶׁר), וְכֵן:"שְׁנוּ רַבּוֹתֵינוּ:"וְטוֹבֵל בְּשֶׁמֶן רַגְלוֹ", זֶה חֶלְקוֹ שֶׁל אָשֵׁר, שֶׁמּוֹשֵׁךְ שֶׁמֶן כְּמַעְיָן"- מַסֶּכֶת מְנָחוֹת פֹּה ע"ב)