Travel Shoes That Take You From Day To Evening
When planning a travel wardrobe, there’s continuum of priorities with packing light on one end, and having the most options on the other. Where you fall on that continuum is really up to you and how you travel; there is no right or wrong position. Because I fall somewhere toward the “packing light” end, I look for clothing and shoes for travel that offer the most versatility.
Above left: earrings | scarf | sweater (similar) | jacket (similar) | jeans (similar) | bracelet | boots
Above right: bag | bracelet | scarf (similar) | sweater (similar) | earrings (similar) | pants | coat (similar) | boots
Traveling In Style
Since my previous post about travel shoes, I’ve received a few requests for some styles that will go from day to evening.
One of the biggest mistakes I made when we began traveling overseas was packing the wrong shoes. I brought a few cute styles (including a pair of 3″ heels) but wound up wearing a pair of simple black loafers almost exclusively. The most stylish choice? Maybe not, but they were the most comfortable pair I’d packed, and I quickly realized they were perfectly appropriate for most venues. Since then, I’ve kept an eye out for footwear that’s both comfortable and meshes with my style.
Think “Smart Casual”
Unless you have an actual Event like a wedding or cocktail party, or are going on a cruise that includes formal dinners, you really won’t need a pair of heels or dressy shoes. “Smart casual” is usually as dressed up as you’ll need to be, and I’ve found the most versatile day-to-evening shoes have these attributes:
- A dark color. Black, navy or charcoal will be your most sophisticated choices. I find black easiest to coordinate, but any darker color in a non-distressed finish will work.
- OR a metallic finish. If black footwear feels to heavy to you, think pewter, platinum or other soft metallics.
- While “athleisure” looks are popular right now, styles with a sleeker design will be more venue-versatile.
The style of shoe will work best for you will depend on your personal style, any foot issues (bunions, orthotics), and the climate where you’re headed. There will always be compromises, though the one thing I’d urge you to never compromise on is comfort.
Ballet Flats and Mary-Janes
If your style is decidedly classic, you might prefer a ballet flat. The trick with this style is to find one with sufficient support and cushioning in the sole. Some may find styles with a low heel or wedge more comfortable than a true flat. Many of you have recommended this style from AGL.
More ballet flats:
Munro | Dansko | Josef Seibel | L’Amour des Pieds | Gabor | Arche | Børn
Mary-Jane, ghillie and ankle strap styles are another alternative if ballet flats don’t provide enough support and stability. Almond, pointed, and squared off toe shapes will look less “little girly” than round toes. A little bit of heel or wedge helps too. Above, an ankle-strap flat from Earthies.
More strappy styles:
Fly London | Pikolinos | L’Amour des Pieds | Rockport | Munro | Gentle Souls
Loafers and Slip-Ons
In all but the coolest months, I’ll usually pack a pair of low-heeled, slip-on shoes. Loafers are a classic choice, but there are a lot of comfortable and good-looking options. Be sure they fit snugly and that your heel doesn’t slip when you walk. Above, a patent leather penny loafer from Paul Green. (This brand is pricey, but makes some of the most comfortable and durable shoes out there.)
More options:
Rieker | Pikolinos | Arche | Paul Green | Ecco | Dansko | Paul Green | Naturalizer
Sneakers and Oxfords
Sneakers in all shapes and colors are now worn (and often considered fashionable) in most parts of the world. For some people with finicky feet, they may be the only style of shoe that’s comfortable enough for the demands of travel. I think a simple, sleek style offers the most versatility for day-to-evening wear. The above from Cole Haan (similar) are subtle enough to fly under the radar when worn as part of a smart casual outfit.
If a sneaker feels just a little too casual, an oxford is another option. The slightly thicker soles that are on trend now can also offer some additional cushioning. Above, this fun and funky style from L’Amour des Pieds (similar) is incredibly comfortable and has removable insoles to accommodate orthotics.
More sneakers and oxfords:
Børn | Mephisto | Beautifeel | Josef Seibel | Pikolinos | Paul Green | Nike | Rieker | Cole Haan
Ankle Boots
I’ve found that ankle boots can be one of the best styles to go from day to evening, and unless I’m traveling someplace very warm, I’ll almost always include them. They can also provide a little more protection in rain and on travel days. Above, these from Paul Green snake-embossed booties (similar) are sharp-looking and comfortable. (They run about 1/2 size smaller than other PG styles.)
More ankle boots:
Naturalizer | Ecco | Børn | Aquatalia* | La Canadienne* | Gentle Souls | Munro | Blondo* | Clarks
*water-resistant styles
What footwear do you find most versatile in your wardrobe?
Stay in touch
Sign up to be notified of new posts and updates from une femme d’un certain âge.
I’m a huge fan of ankle boots – just had to replace a pair that were so comfortable I could have slept in them (and consequently wore them all the time). Good tips – thank you!
Although I’m not a huge fan of Mary-Jane style shoes, I bought a pair of Naot Kirei’s recently on the advice of a shoe fit specialist. I wore them on a trip to Ireland and Paris and they were comfortable and provided a lot of support. Mine are black suede and calf and certainly fall into the category of “smart casuaI.” I also have several pairs of Naot Kayla sandals and they, too, have good support.
I am a big fan of Cole Haan’s Grand line of shoes. They have the bottom of an athletic shoe and the top of a smart shoe. I wear the oxfords with a contrasting sole and never fail to get compliments on them. I have a pair in dove grey with a pink sole and a pair in black with a white sole.
While I love the look of a ballet flat, I can never wear shoes without socks and can’t find a comfortable sock liner that doesn’t fling itself off my foot while walking.
Ditto the need to wear socks. Also, I have completely lost the fat pad on the ball of my foot. Unless my shoes are well padded I feel each and every cobble. That Agl flat is the most comfortable flat I have ever owned for these finicky feet of mine.
Susan, the lace no show liners you recommended back in 2015 are sold out. Any new suggestions? I can’t find any that don’t slip off the heel. Thanks
Hi Sharon, I’ve been using Smartwool Secret Sleuth liners for the past year or so and love them. They stay on, don’t get stinky and are comfortable even in warm weather.
I love those! Throw out your packaged cotton stretch-out no shows! The Smartwools , while not cheap, are worth it. The elastic is durable and wool performs. 6pm.com often has them. I bought my first pair on the sale rack at Nordstrom and have purchased them at full price because they are worth it!
I just purchased a pair of sleek sneakers by Beautifeel. The style is Cella and they are currently on sale at the walking company. They have nice padding, some support and a much slimmer profile. With a black patent toe, black suede drizzled lightly with silver sides and velvet laces they can stand up to a slightly dressier occasion. I’ve tried on a million sneakers, this is the first one I’ve brought home
Would love comments and suggestions for stylish, comfortable shoes that have a wide toe box or come in a wide width.
I find Ziera shoes very comfortable for my wide feet
I wear Fresh Foam New Balance sneakers which accommodate my very high arch and wide feet. For every day I like the Dansko Patti shoe. I’ve had really good luck with the Cole Haan Sadie shoe too for a dressier look. Hope that helps.
Great selection. I have no idea what kind of shoes or size I will wear when my foot heals. But you’ve given me lots of chic choices. That was my problem. Wanting to look chic for my tree trimmers! I fell off my clogs!
Comfortable, arch-supporting, day-to-night shoes are the Holy Grail of travel shoes.
My Ecco oxfords will go all day, but they are a little clunky for dinner (although they seem to be trendy now, to my surprise.) My Clark Wave Mary Janes tried to be the answer, but the round toes look too school-girlish. Booties are out because I don’t like something hitting my ankle,
Clark “Timeless” loafers are my answer for now. They pack light, look reasonably sleek, and I could walk a few miles in them, although not all day. Still, the search goes on. (I must admit, my standards go up when Paris is on the itinerary.)
Most comfortable shoe I’ve ever travelled in are my NAOT black/sort of metallic shimmer, lace up oxfords. Could walk forever in them – also took a pair of metallic NAOT sandals with me to the UK last Sept – wore them several times as it was warm enough – have them in several colours – really comfortable and the straps adjust. NAOT seems to fit my feet very well re the arch.
I have the AGL flats you have pictured and love them!
Such a helpful blog post. It’s feeling the wanderlust.
I pulled out all my time tested travels shoes (comfortable but fashionable enough to fit the occasion). I’ve come up with Ecco’s, Arches and Alegria sandals.
I’ve been using a pair of Fitflop Uberknit for long walks. Mine are a “gym worthy” color, so I’ll be ordering them in black/silveer for urban travel. These fit the bill for my grumpy big toes.
The hunt for comfortable travel shoes continues! I’m going to try the Cole Haan sneakers. I have a couple of pairs of their Sadie wedge shoes in black and nude and they’re very comfortable. I usually wear New Balance Fresh Foam sneakers but the Zerogrand look much more stylish. As usual, thanks so much for sharing your always helpful hints with us!
These are great recommendations! When I saw the Cole Haan sneaker, I immediately thought of Allbirds Wool Runners as another possibility for those who like that style. I pulled the trigger on them recently (in Chili, for fun) and couldn’t be happier. They are incredibly comfortable and best of all, I can wear them without socks! Really and truly – the wool seems to let my feet breathe. This is the only pair of shoes of any kind that I’ve ever had that do not leave my feet feeling sticky and sweaty when I try wearing them without socks.
https://www.allbirds.com/products/womens-wool-runners?variant=29693050247
If going to a city, I really suggest wearing a shoe that can’t slide off easily, like a sleek sneaker or ankle boot. Those are the two kinds of shoes I take. Slip on shoes like loafers and ballet flats can easily slide off your feet. A tourist once stepped on the back of my loafer when I was getting on the subway and the loafer ended up on the subway tracks. As a result, I found myself on a subway in the middle of winter wearing only one shoe and figuring how I was going to get home. Luckily I just happened to have another pair of shoes in my bag I was bringing home. After that, I stopped wearing slip on shoes for commuting or touring.
As for what to wear on your feet if you do wear ballet flats, I suggest nude knee high stockings. I wear them all the time. They are comfortable and you don’t have to worry about them slipping off your feet like no show socks.
For years I resisted wearing sneakers in my “off hours” (I’m a fitness pro). That changed when I bought a funky, chunky pair of rose gold leather and black fabric New Balance sneakers. It must be the metallic leather, but I have never received so many compliments on any item of clothing/shoes. From young to old, from chic to homeless, people constantly admire them! I wear them even with “dressy” pants, with no-show athletic socks, and a Uniqlo down puffer and feel fantastic and well-dressed. My feet feel great, and I save money by walking to my destinations rather than needing to limp into an Uber or taxi! I think the trick was embracing the sneaker-ness, not trying to hide it. Is this the shoe version of the concept of “jolie laide?” I love it!