In 1853 the Emigrant’s Guide to Australia advised prospective emigrants that, ‘As regards clothing, the points to consider, for the permanent stock, are utility and durability; anything for mere show would be worse than useless’. This chapter investigates the difference between dress expectations and the realities of colonial life, and shows how fashion not only expressed status and prosperity, but also how settlers actively shaped their dress culture within the shifting boundaries of a colonial society-in-the-making. Private journals and newspaper articles provide an insight into the experience of emigration and buried within the accounts are references to clothing requirements for those venturing to Australia. While emigrants often experienced a mismatch between what they were told about Australian society and what they found, they generally packed garments that they already owned and that conformed to their own experience of everyday dress.