Looking for comfortable outdoor shoes that look nice enough for dinner

March 17, 2019 9:55 AM

I'm looking for what may be an impossible hybrid: Shoes that are appropriate for a light trail hike, but also look nice or at least unobtrusive enough to wear with nicer clothes to go into town for dinner. Most "walking shoes" are either too flimsy or too nice for off-sidewalk adventures, or are too ugly for me to consider wearing them with nicer clothes, but I'm open to any and all suggestions! Womens 9-9.5 if it's relevant. Low boots are OK, too.
posted by rhiannonstone to Shopping (13 answers total)

Response by poster: I should add that this is for fall/winter/spring hiking, since in the summer it's easy for me to throw a nice pair of sandals in my bag without taking up too much room. Because that's my main goal here: pack minimally while still taking care of my feet during adventures and feeling cute when I clean up and go out after them.
posted by rhiannonstone at 9:59 AM on March 17, 2019

Even the dressiest Keens are pretty solid hikers, not sure if they have models dressy enough for the kind of dinner/kind of town you’re thinking about.
posted by SaltySalticid at 10:05 AM on March 17, 2019 [3 favorites]

When you say "too flimsy," do you mean in terms of sole stiffness?

I've done some very light hiking in my (men's) Clarks boots. Admittedly, this was more of "walk on a slightly sloping, slightly stony path for a couple of miles before dinner" than anything that would require something sturdier than sneakers, so maybe the soles are still thinner/more flexible than what you're looking for.
posted by pykrete jungle at 10:13 AM on March 17, 2019

Response by poster: "Too flimsy" either as in "not supportive enough" or as in "sole or uppers will not come out the other side of a 2-mile trail hike without permanent damage".
posted by rhiannonstone at 10:29 AM on March 17, 2019

Not sure how dressy you're planning to be, but I wore these for a long time. I would think the bigger issue for hiking and then dining would be that the shoes would be likely to get dirty.
posted by If only I had a penguin... at 10:38 AM on March 17, 2019

I would take a look at Naot shoes, if you're looking to do a lot of walking around on nice shoes and then transitioning to dinner.
posted by vivzan at 10:47 AM on March 17, 2019 [1 favorite]

What is dressy for you? Slacks and a cute button up? Dress and a cardigan? Dark jeans with a sweater? I own these timberland chelsea boots in black and they're my every-day shoes. They don't do well on ice, but are good for general walking around in the woods purposes, and I've worn them out as well. They're no longer for sale, but i'd suggest something like that.
posted by FirstMateKate at 11:03 AM on March 17, 2019 [2 favorites]

Would something like this boot work? These are the least technical/sporty looking hiking boot I found, and I could see wearing them with tights or leggings pretty unobtrusively.
posted by MadamM at 11:04 AM on March 17, 2019 [3 favorites]

The bizarrely-named Merrell Siren Guided LTR Q2 Hiking Shoes in espresso suede. (Have you considered packing folding ballet flats for evening?)
posted by Iris Gambol at 11:30 AM on March 17, 2019 [1 favorite]

Yeah, if sandals are a good summer solution then folding flats might be a good other-three-season solution. I have two pairs of Yosi Samras; the metallic ones haven't held up super well but the suede are still in impeccable shape ~4 years later. They fold up tiny and come with a cute little bag, and they are plenty light enough to stick in a purse or backpack. (I too have been on an epic multiyear search for shoes that "can do both", if you will, and have had no luck, partly because even when I find shoes that look right, they still gets dirty enough on trails that they're not a viable dinner solution.)
posted by goodbyewaffles at 1:41 PM on March 17, 2019 [1 favorite]

How do you define dressy? What about Blundstones? Their boots go nicely with skirts, etc.
posted by stillmoving at 2:17 PM on March 17, 2019 [1 favorite]

I have these, which I got for reasons similar to yours, and they’ve held up pretty well.
posted by Empidonax at 7:46 PM on March 17, 2019

Cole Haan makes a couple of cute "hikers" that I think could look dressy (maybe the black ones)? I have taken them on short hikes and have been surprised with the level of support.
posted by something_witty at 10:28 AM on March 18, 2019