A new class of non-ionic amphiphiles have been synthesised using a combination of polyethylene glycol (PEG) and oligoglycerol dendrons as hydrophilic units and an alkoxy aryl moiety as hydrophobic unit. The resulting amphiphiles were found to aggregate in aqueous medium. Their aggregation behaviour was studied using dynamic light scattering (DLS), fluorescence spectroscopy, and cryogenic electron microscopy (cryo-TEM). The inner hydrophobic core of these aggregates in aqueous medium is capable of encapsulating lipophilic guest molecules. The encapsulation behaviour was studied using Nile red as a hydrophobic dye as well as Curcumin and Dexamethasone as hydrophobic drug candidates. Furthermore, for biological evaluation, cytotoxicity and cellular uptake was studied using different cancer cell lines. The biomedical application of synthesised amphiphiles was further investigated for dermal drug delivery on excised human skin using Nile red encapsulated in the nanocarrier. The release profile of drug/dye encapsulated amphiphiles was studied under physiochemical conditions in the presence of immobilized lipase Novozym 435.