Comfortable & Stylish Walking Shoes for the Jet-setting Fashionista


I’ve just finalized my vacation plans for Rome next month, and–after reserving a timeslot to visit Villa Borghese and brushing up on my Italian–I’m left with that other travel question, the nagging sartorial quandary that faces all jet-setting fashionistas: where can I find walking shoes that are both stylish and comfortable? Does such footwear even exist?

I know that Tom’s has launched fashion forward collections, but no matter how hard I try, I just can’t bring myself to wear them (and don’t bother preaching to me about the double- padded Nordstrom variety. I still can’t do it). Judging by how hideous Memphistos are, they must be comfortable. And don’t even get me started on Merrells (cringe). Looking at them physically hurts me, and my mother has taken to preemptively apologizing to me whenever she’s going to wear them.

I’m going to be in Rome for heaven’s sake; between the architecture, the fine art and Sophia Loren, the city practically invented beauty. It would be blasphemous to walk those ancient streets in ugly footwear. With that said, I’m no longer willing to sacrifice comfort for glamour. That boat sailed somewhere around my mid twenties. I need shoes that are as pleasant to walk in as they are to look at.

To find such a pair I turned that resource of all resources: the Internet. After poring over hundreds of footwear reviews, I extracted eight styles that were aesthetically acceptable and allegedly comfortable. I ordered them from from e-retailers that offered free returns and proceeded to test the shoes out on the safety of the rugs in my house. With a limited budget, I scrutinized each pair for style and comfort, selected the best to keep for my trip to Rome and returned all the others.

Check out this video of the shoes in action, then scroll down for my style-by-style reviews….




Charles Philip Shanghai Gaby Loafer in Leopard, around $175

Appeal: I love the elegant East meets West aesthetic of these handmade slippers and their colorful, eyecatching print.

First Impression: The packaging was exceptionally lovely, and the shoes are very well made, including thoughtful details such as snakeskin embossing on the leather ring around the midsole. The inside is nicely padded (although there isn’t much arch support) and the outer leopard print fabric is made of a soft calf hair. They’re certainly comfortable enough to walk the mile to my favorite coffee shop in San Francisco, but I fear that they’re too delicate to hold up to a week of walking around Europe.

Verdict: Despite their impressive style and comfort, I’m returning these shoes; They’re too expensive to keep only to immediately wear them ragged.


Quincy Tye by Frye in Red Sunwash Nubuck, around $140

Appeal: I love the preppy nonchalance of these poppy hued boat shoes. They make me imagine jumping on a sailboat with a pair of dark denim rolled at the ankles, Jackie O sunglasses on my face and an Hermes scarf tied around my head–and these loafres on my feet!

First Impression: Wow! These are the softest, most comfortable shoes my feet have ever slipped into. The leather is buttery, the style refined and the shoes are every bit as wonderful as the Zappos reviews claimed. And they have that effortlessly chic nautical vibe I was dreaming of.

Verdict: The quincy is a definite keeper. The only question left is which size to keep. My standard 7.5 in this style felt a bit little loose and since the leather seems prone to stretching, it might be more prudent to order down a size and let it mold to my foot.



Frye’s Wyatt Harness Short Boot in Dark Brown Antique, around $240

Appeal: Like the Donnie and Marie, this boot is a little bit country a little rock ‘n roll–and completely stylish.

First Impression: I really wanted to fall in love with these, but I only fell in like with them. They made my feet look big and I’m not convinced they really flattered my legs, but I still love the slightly edgy look. They were well made and comfortable–with lots of room around the toe box, which my bunions appreciated–and I’m confident would get lots of use.

Verdict: While I really liked them, I just didn’t love them enough to fork over that large a piece of my budget at this time. They’re going back for now but staying on my wish list hopefully to be purchased at a later date.


women's pluggz loafers emerald
Pluggz Suede Emerald Vesta Loafer, $139

Appeal: Oodles of supportive features, like a trampoline heel, memory foam inserts, moisture wicking anti-microbial lining  and a padded arch made these loafers seem like they had marathon walking prowess. Plus, they have “grounding” technology that claims to energize you by facilitating the passing electrons in the ground up to the body through a conductive plug (hence the name) in the shoe’s sole.

First Impression: The shoe is much more attractive than anticipated. The slip-resistant rubber sole seemed a tad clunky in pictures, but that part of the shoe is completely out of eyesight when on the foot. The color is a striking, rich emerald green, and the shoe has a sophisticated smoking slipper appeal. It ran about one full size small.

Verdict: Didn’t experience any of the “grounding” benefits, but I love how supremely walkable the shoe is. A definite keeper that will be getting lots of mileage.


Reagan Campus Driver in Grey Dakota, around $100

Appeal: The soft leather looked expensive and comfortable, and I liked the hybrid moccasin-meets-driving loafer style.

First Impression: The color and leather are beautiful, but the shoe is boxier than expected. It’s very comfortable and has a cushioned sole and arch support, but it’s not quite as comfortable as the Quincy Tye.

Verdict: Great shoe, but not quite sleek enough to suit my style. They’re getting returned.


frye regina ballet flat black

Frye Regina Ballet Flat in Black, around $135

Appeal: This refined pointy toe ballet flat is just what I need to round out my wardrobe as it looks great with dresses and skirts, compliments skinny jeans and is nearly mandatory to feminize slouchy boyfriend jeans.

First Impression: Extremely chic and elegant on the foot. I felt like a modern day Audrey Hepburn. The sole was more cushioned than a typical ballet flat, like the Tory Burch Reva, but it was far from cushy and lacked arch support. Because the shoe has a pointed toe shape, the toe box is small and the edge of the leather is low on the foot, putting pressure on my big toe/bunion area. This was perhaps emphasized by the shoe running small all around. I wish I had ordered up half a size from my normal size.

Verdict: A truly beautiful shoe that would be great for work and will stay on my wish list; however, it felt like it would require breaking in and isn’t quite comfortable enough to wear walking all day around Rome.



The Jackie Button Boot in Cognac Soft Vintage Leather, around $370

Appeal: These boots ooze with rustic charm; while they come in a variety of leather colors, I loved the rich cognac. It reminded me of blend between a classic Chloe boot and a Ralph Lauren take on the cowboy boot. Parfait!

First Impression: Gorgeous. So gorgeous in fact that I immediately (and recklessly) wore them out (as seen in this post) making them unreturnable and blowing a huge chunk of my budget.

Verdict: These boots are not only sophisticated looking but they flatter the leg and give the aesthetic benefits of a heel without the discomfort. No, I wouldn’t wear them to walk from one end of Rome to the other, but I would wear them for a long afternoon on the town and still be able to wear them out to dinner that night. Note: to make them even more walkable on my vacation, I purchased Superfeet Insoles.



Uggs Hally in Night Canvas, around $70

Appeal: A Converse Allstar-inspired take on the comfortable sneaker spiced up with Uggs signature lambswool lining.

First Impression: I love the extremely cushy and supportive sole and the patch of soft lambswool that covers the blister-prone heel area. They’re a bit clunkier than I expected, but still sleeker than regular athletic sneakers. I feel like I could wear these all day comfortably.

Verdict: While these aren’t the most glamorous shoes in the bunch, they’re attractive enough that I’ll wear them, and by the fourth straight day of walking, I’m going to want a shoe this athletic and supportive to hoof around the Eternal City in.


Frye Regina Disk Ballet Flats in Black, around $75

Appeal: Just like the basic Regina’s, but with the some visual interest in the form of decorative silver studs. Plus, they’re on sale, so I thought I would check them out in the hopes that I like them more than the twice-the-price basic Regina Flats.

First Impression: They have a great shape and the studs are a nice embellishment, but the back side of the studs are hard beneath the leather and dig into my foot, especially around the big toe/bunion area making them uncomfortable even to try on.

Verdict: While I liked style, but the discomfort these shoes caused my feet made it an easy decision to return them.


What are your favorite walking shoes?


6 Comments on Comfortable & Stylish Walking Shoes for the Jet-setting Fashionista

  1. elle
    January 26, 2014 at 9:58 pm (4 years ago)

    So this is a puzzle. I adored the flat pointy, and think you should zero in on that style , from a diffenent maker. When you find a pair that is comfy, buy three.
    Also loved the shirt boots.. They will go on sale I hope .
    Loved your video.
    Get shopping and packing ! What a wonderfully trip you will have,
    XX,, Elle

  2. Jacq
    January 27, 2014 at 8:55 am (4 years ago)

    when are you going to Rome?! We had our honeymoon in Italy, and like you, I was unwilling to be encased in jeans and tennis shoes. Just takes the romance out of it for me. I got a lot of mileage out of my boots and bought some padded inserts to help out some of my flatter-flats. I wore through them, but they saved my feet for most of the 10 day trip.
    The other thing that i think is a necessity for travel is a stylish raincoat. That way, even in poor weather, you have a cute “outfit” for your pictures.

  3. Maggie Winterfeldt
    January 27, 2014 at 12:37 pm (4 years ago)

    Heading to Rome mid-February with my family! I bought some Superfeet insoles for the Frye boots, and I’ll take your advice and do the same if I find a pair of ballet flats I love! Great suggestion about the raincoat. A fabulous jacket makes everything else look great–or at least covers up what doesn’t look great. You went in March, right? Did it rain a lot when you were there?

  4. Wendy G
    February 11, 2015 at 9:16 pm (3 years ago)

    Which did you end up wearing for LOTS of walking?