I know, I know—January is supposed to be the time for fresh starts, followed by the renewal of spring cleaning. But honestly? Fall is when I truly feel that “beginning anew” energy. Maybe it’s the nostalgia for back-to-school shopping, with crisp new notebooks and freshly sharpened pencils, or perhaps it’s the final release from summer’s heat that sends me running toward all things cozy and comforting. Whatever the reason, there’s something about this season that awakens a sense of excitement and possibility in me.
It doesn’t hurt that fall is also my favorite season for travel. There’s something magical about exploring new places when the air turns crisp, the leaves start to change, and locals sigh from the release of summer’s crowds.
And let’s not forget the fashion. Fall is the time when I love swapping out breezy sundresses for chunky sweaters and slipping into ankle boots instead of sandals. The sartorial shift feels like a perfect match for the season’s energy—like we’re all collectively getting ready to step into something new.
With this fresh energy and desire to explore, one thing is for sure: all the adventures fall has to offer require a comfortable and stylish pair of shoes to carry you through the season.
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So what makes a good travel shoe? A good travel shoe offers support where you need it, can carry you for miles without blistering, and suits the destination’s preferred style (say, flats in Paris or rugged boots in the PNW). As someone who travels solely with a carry-on or personal item, versatility is a plus—the best travel shoes can take you from an afternoon of sightseeing to a swanky restaurant without wasting precious vacation time at the hotel to swap your shoes.
As we see trends come and go at lightning speed (remember mesh flats?), it can be challenging to find shoes that feel both current and timeless. With that in mind, today I’m rounding up my top picks for quality travel shoes that not only feel fresh this season, but that will take you on adventures for years to come. And because suddenly everyone in my social feeds is fretting over socks, I’m addressing that topic here too.
What do you say? Let’s walk right over to the good stuff:
MY FAVORITE FALL TRAVEL SHOES FOR 2024
Ten fun pairs for autumn adventures
1. Slingback Flats | Every travel wardrobe could use a practical flat, and I like that these have a little edge. With oversized buckles and a sharp triangular shape that carries through to the hardware, this pair is perfect for toeing the line between daring and demure. Plus, the slingback styling is perfect for cooling your heels on those unexpectedly warm fall days.
2. Bold Block Heels | If you’re going to travel in a heel, make it a safe one. Whether you’re attending an elegant dinner or a wedding, this block heel pump is far more sturdy than its stiletto counterparts, plus memory foam cushioning means you can walk for miles. Play up the vintage silhouette with similarly old-school styling, or give your contemporary pieces a fun twist (you may find these so comfortable you’ll want to wear them with everything in your suitcase – even jeans!).
3. Waterproof Chelsea Boots | Sometimes you need to navigate icy streets during the day and head straight to the theatre at night. This pair of waterproof Chelsea boots is rugged enough to tackle all your sightseeing while remaining relatively understated. Pair them with a dress, tights, and your chicest coat for maximum impact.
4. Knee-High Boots | While I personally find that tall boots are a little less versatile for the carry-on lifestyle, your wardrobe may be primed and ready to rock them. This pair has a bit of a Western vibe (which feels very of-the-moment) yet they aren’t overt cowboy boots, making them ready for the long haul. Which, coincidentally is when you’ll want to wear them: on the plane, to save precious suitcase space.
5. Hiking Boots | Hitting the trails and the streets? A pair of rugged waterproof boots with ankle support are your best bet. This boot is sturdy enough for casual hikes yet sleek enough that you won’t look out of place at your post-hike watering hole. As with all new boots, give them a good breaking-in before you head out on your trek.
6. Mary Janes | If you can only take one pair of shoes on your next city break, this is my pick: a nice, neutral flat that is secure on your foot and goes with everything. But this pair kicks things up a notch with pillowy cushioning, an anti-blister lining, and reinforced leather soles. Get ready to walk all day and dance all night!
7. Loafers | You know what? Now that I’m not in the office every day, I kind of love the workwear-as-casual-wear trend. Nothing embodies this inspiration more than a loafer, wouldn’t you say? Opt for a fun classic menswear-inspired pair like this one at your next destination, and everyone may just assume you’re a local. Excuse me, can I ask you for directions?
8. Sneakers | My lower back rejoiced when sneaker trends shifted to more supportive pairs of sneakers, but these travel sneakers have all the bells and whistles: a waterproof exterior, grippy sole, thermoregulating capabilities, and they are hand washable. And yes, they do look cool.
9. Ballet Flats | By now you’ve probably heard that ballet flats are back—and by now you’ve also probably heard that they’re bad for your feet. Thankfully, shoe brands have caught up with the times and are now making flats that offer more arch and heel support along with a wider toe box. This is one of those pairs, and it’s offered in a delicious colorway.
10. Clogs | There’s a reason clogs are the preferred choice of shoe for people in professions that require lots of standing all day (looking at you and feeling oh-so-grateful, teachers and nurses). This gorgeous pair feels fresh and modern, and they can be easily warmed up by a pair of socks when the temperature starts to dip. But more on socks later…
CARING FOR SHOES IN THE FALL
Proper shoe care extends the life of your pair for miles
I’m willing to bet that some of your fall shoes will make their way into early winter with you, so now’s the time to stop and properly care for them. Thanks to comfortable temperatures, fall travel usually involves extended periods of walking, which means more wear on your soles.
It’s a great time to flip your shoes over and examine the bottoms; if you see lots of wear on your leather soles, it’s probably a good idea to take them to the cobbler to have them resoled. Even if you’re ordering a new pair from the list above, it wouldn’t be a bad idea to take them in to have a non-slip welt added to the bottom or you can always purchase grips to add on your own.
Rain can often work its way into the forecast in this season, though hopefully sparingly. Be prepared for those sudden downpours by using a waterproofing product for protection. While you’re here, you can also give your other shoes a good conditioning (they may be thirsty after a dry summer!). I like to designate a sleepy Sunday as a shoe care day every now and then to knock it all out at once. Pop in a good podcast or audiobook about your next destination, and get buffing!
TO SHOW OR NOT TO SHOW, THAT IS THE QUESTION
We can't talk about shoes in 2024 without talking about socks as well...
Ah, the great sock debate of 2024.
If you’ve scrolled social media this year, you’ve seen that socks are back in a big way and people have feelings about it. You’ve heard people wondering aloud what type of sock to wear with what shoe, or others decreeing that socks must be showing at all times or else.
In my opinion, there should be no hard and fast rules in fashion—because that’s not style, that’s conformity—but if you’re just dipping your toes back into the sock trend (both literally and figuratively), here are a few pairs to play with this season:
Believe it or not, fun socks may just be the easiest way to break into the habit of wearing socks again. I love a good sheer sock, especially when it has an interesting pattern like these grid socks. Lettuce edge socks in fun colors are also great for pairing with skirts to show off their ruffled flair.
As for the basics, I like thin crew and trouser socks for Fall because they keep a sleek profile and actually stay up (save those ultra-thick wool socks for winter; trust me, you’ll have plenty of time to wear them!). I still reach for my no-show socks on occasion, but I have to say, I don’t miss digging around in my shoe to fish out the heel when it inevitably slips down…
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FINAL THOUGHTS ON STYLISH AND COMFORTABLE TRAVEL SHOES FOR FALL
At one point in time, “stylish” and “comfortable” were two separate categories of shoes, but I’m so thrilled that shoe brands now creating footwear that manages to be both at the same time. As travelers, we deserve to look and feel good at our destination, leaving us free to focus on the experiences that lie ahead of us.
Still, even the most comfortable pair of shoes may require a little breaking in. So don’t shop for shoes right before a trip; instead, figure out what gaps you have in your shoe wardrobe well in advance. This means you’ll have plenty of time to ease into a new pair (I love all of these helpful tips for breaking in new shoes) and spend zero time tending to blisters in the middle of your trip. So—where are we off to this season?
Thank you to the team at Poppy Barley for making today’s post possible! New to the brand? You can save $30 on your first purchase by shopping through my referral link. Thanks for supporting the brands that support this blog!
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Questions for you
Socks – how are ya feeling about them?
What shoes are you most excited to wear this season?
What Fall adventures are on your calendar?
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