Though years had passed and I was no longer a city-hopping student, I figured my best bet to enjoy my time in Portugal was to look to that era for inspiration. The strategy was simple. I packed two T-shirts (black and white, of course), one long-sleeved shirt, one pair of wide-leg pants, two jackets (one denim and one leather), and a pair of dark wash jeans. I also brought two blazers for warmer days, as well as accessories that would enhance the otherwise boring outfits, including a velvet hair bow. For shoes, sneakers were my go-tos, bringing with me one pair for long walking days in nature settings and another for city adventures.