Jaunted

Tsubo Shoes for Men and Women: $80-$220.
Although you may be tempted to break out the Ugg boots, that's not something we're recommending here. Nu uh. Instead, look to another of their family of brands, Tsubo, which does something most other shoes have tried and failed at: combining travel-friendly constant comfort with more than a shred of style.

They make lines for both men (see top three) and women (see bottom three), and the women's shoes in particular are designed so as not to get stuck or be unsteady on cobblestones (hello, Italy). We've got the "Peary" wedge (see in the very first picture), and we call them our "Tokyo shoes," since they're perfect for a Tokyo trip, for which we pack far more fashionably but still need the comfort. The men's shoe styles are surprisingly fashion-forward as well, and all work to prevent you from being marked as a white Reebok-wearing, polo shirt-donning sort of culturally indifferent tourist.

Keds Pro, Keds Collective & Keds for the Whitney Museum: $60-$100.
When was the last time you even considered trying on Keds, let along purchase them for travel? Yeah, probably a loooong time ago, maybe never. But in the last couple of years, we've slowly become reacquainted with them and um yea, we've actually started packing them in our luggage.

As a rule, they're unisex and, even better, the most expensive leather pairs usually max out at $100.
We've got the Whitney Museum of Art Keds, by artist Jenny Holzer (shown at right), which we love because 100% of the profits go directly to benefit the museum, which, if you're planning a trip to NYC, you'll probably be visiting. Plus, Keds are thin, light, not so expensive you cry over a ruined pair, and they offer a design-your-own option (itinerary map print, anyone?).

The Fold-over Boot: $85-$250.
Alright, let's talk boots. Whereas over-the-knee was popular last winter for women, it's not back so much and plus, those things are just about the worst shoes to travel with. Instead, it's the slightly pirate-influenced, fold-over boot, which is thankfully pretty easy to slip in and out of at security checkpoint and easy to match to most any outfit.

Whether low-top (like the Keep shoe shown at middle) or high-top (like the Allsaints men's boot at left or the Dolce Vita women's pair at right), the fold-over boot typically looks like you've had them for years, so any travel-induced wear and tear will nicely add to the character of the shoes. And for ladies, they are ideal for tucking in your jeggings & leggings.

[Photos: Jaunted, Tsubo, Keds, Allsaints, Keep, Dolce Vita]