One shoe for a week of city walking

[ezwicky]

In the interest of packing as light as possible, I'm thinking about just one pair of shoes in addition to my hiking boots and suede drivers to take on an overseas vacation where we'll have five days of exploring one of our favorite cities. The week prior will be hiking in the mountains, hence the boots.

Trousers will be a pair of jeans and a light-colored linen trousers. Jacket will be charcoal fresco. Shirts will range from plain t-shirts to polos to merino sweaters.

Weather could be anywhere from 40s at night to low 80s in the day. Could be rainy, could be fair.

My shoe choices are:

1) Brown suede chukka boots
2) Brown wingtips (I'm wearing them for work this week in Phoenix and they're very comfortable)
3) Light brown non-penny loafers. Smooth and plain.
4) Black cap-toe derby, pretty well worn-in.

Open to any other suggestions too. I have six weeks to break in a new pair...

Thanks in advance,

Eric Z
Richmond VA
USA

 

[johng70]

So, the black ones are out (not a good match for light linen trousers IMO).
Loafers are the most common style of shoe with linen pants. Linen is a more casual pant so they just work well together. My concern would be how your loafers will hold up to a lot of walking. For me it would be between the loafers and the brown wingtips. If equally comfortable with a lot of standing/walking then the loafers but if the wingtips are going to hold up better for the walking go that route.

 

[Easily Amused]

If they have rubber soles, I'd say the brown suede chukka boots. I've done a lot of vacation pavement pounding in boots during the summer. I find rubber soled chukka (and chelsea) boots super-versatile and comfortable, unless you're planning to wear shorts (which I didn't see).

Another option to consider would be espadrilles, depending on how much you'll be walking.

 

[ezwicky]

Dainite soles on the chukkas. No espadrilles at the moment. Thanks guys for the replies!