Do I need a waterproof shoe for travel, or is a regular sneaker fine?
It depends on the itinerary. If rain, snow, or uneven trail is likely, the waterproof mid-cut hiker is the only shoe on this list built for that. For dry, paved city travel, any of the casual sneakers or flats will hold up fine without the added weight of a waterproof shoe.
Which of these packs down the smallest for carry-on luggage?
The pointed-toe flat and the boat shoe both have low-profile, slip-on constructions that take up noticeably less suitcase space than the mid-cut hiker or the walking sneaker, which have more structure and bulk.
Is a walking shoe necessary if I'm only doing light sightseeing?
Not necessarily. A dedicated walking shoe earns its keep on high-mileage days, but for lighter itineraries a casual sneaker, boat shoe, or flat from this list will be plenty comfortable without the more sporty look.
Can any of these double as a work-travel shoe for meetings?
The stitchlite oxford is the most meeting-appropriate option here given its lace-up dress styling, with the pointed-toe flat as a close second. The clog-style professional shoe leans more toward standing-shift comfort than boardroom style.
What's the best option for a warm-weather or beach trip?
The wedge sandal and the leather boat shoe are the two warm-weather-oriented picks on this list, with the sandal being the only fully open style and the boat shoe offering a bit more coverage.
How do I choose between the three sneaker-style options?
The washable knit sneaker prioritizes easy care, the Go Walk model is built specifically as a walking shoe for high mileage, and the running-style sneaker is the most general-purpose, casual option of the three — none are marketed as waterproof or technical hikers.