Let’s talk about the problem that got the bronze medal in the poll but wins the gold for suitcase space: SHOES.

“They take up my whole bag.”

That’s how you voted, and I felt that in my soul, because I just spent WEEKS on my own fall shoe decisions.

(I wrote about your #1 problem here, and #2 problem here ICYMI)

Here’s what happened: I pack bottoms first, always. So my fall bottoms were chosen. And then I could not find ONE pair of shoes that worked with ALL of them. Not one.

And I had an extra complication that made this even trickier: I’m a sandals girl.

Born and raised in the Caribbean coast of Venezuela, my feet have opinions about closed shoes.

I love the look of boots, I love the idea of boots, but I genuinely struggle with closed shoes.

My feet need to be free 😅

So I wasn’t just picking fall shoes, I was hunting for the mythical perfect pair of boots: cute enough to want, comfortable enough for my sandals-spoiled feet.

So my notes app turned into a shoe museum. You sent me the BEST suggestions (more on those in a minute), and I finally made my decisions.

So today: my thought process, my picks and the honest answer to the bulky shoe question so many of you asked.

First, the rule that makes fall shoes hard (and then easy):

✅ Your shoes match all your BOTTOMS, not just one outfit.

Every pair you pack has to work with every single bottom in your suitcase. If a shoe only works with one outfit, it’s not a travel shoe.

This is exactly why fall is harder than summer. In summer, sandals and sneakers go with *almost* everything.

In fall, suddenly there are tights, wide leg pants, skinny jeans, different hem lengths, rain… and most shoes start failing the “match every bottom” test.

✅ The 3 jobs test.

Every fall trip has three shoe jobs: all day walking, wet weather, and nicer dinners.

The goal is pairs that hold more than one job each. Keep that in mind while I show you my picks, because it’s the whole reason my final number is so small.

✅ Quick styling rules while we’re here:

👖 Wide leg pants: full length hems want a little height under them (a bootie) so the hem falls clean. Cropped styles do the opposite: they show off the shoe, so sneakers or loafers shine.

🎨 When you match your boot color to your pant color your legs go on for days.

🧦 Skirts and dresses in fall = booties with tights.

📏 Buying boots? Order a half size up, and before the trip, test your THICK socks with the exact shoes you'll wear them with. A boot that fits with no-show socks and chokes with merino socks will betray you mid trip.

🌧️ And never, EVER suede at very rainy destinations. If you spray them, they can handle a few puddles, but suede won't handle Milan in November.

I put this little image together as a general guide for you to save ⬇️

This is just a guide. There are obviously exceptions. This is not written in stone and of course, your personal style and the pieces you're wearing play a huge role. Just take it with a grain of salt 😉

Now. My picks for 3 months of Northern Italy.

Full honesty first: I haven’t left yet. These decisions are final, but nothing is tested. Once I’m there, you’ll see every pair in action with outfit photos every single day I’m testing a packing list. If something fails me, you’ll know.

👟 Vessi sneakers: SO many of you recommended this brand that I finally went for it, and you were right. They needed ZERO breaking in. None. I’m still shocked (my sandals-spoiled feet approve).

I got the Selene/Hyperpink color, which sounds louder than it is: they’re white sneakers with a small pink detail on the back (and they come in other colors too, including all white).

Jobs covered: walking + rain + casual dinners

👢 The Italian leather stretch sock booties from Quince: ordered, waiting for me at my in laws’ with everything else. I think THIS is the pair that solves the "matching every single bottom piece".

A sock bootie has a slim, seamless shape, so it disappears under wide leg hems and looks sleek with tights and skirts. Nothing to argue with. And for a sandals girl, the stretch women rave about in the reviews might be exactly what makes a boot finally feel wearable all day. That’s the bet, anyway.

Jobs covered: dinner + walking + warmth.

And actually... that might be it. Two pairs for three months 😳

I’m not 100% decided yet, because these loafers are tempting me.

They have to pass one exam first: do they look good with tights? If yes, they might sneak in.

Plus, I always have my trail runners, because we’re planning to sign up for gyms in both Milan and Verona. Those live in the gym bag category, not the outfit category because I rarely wear them outside the gym.

So yes: mostly sneakers, all fall, in Northern Italy. On purpose.

Is that a stupid choice for a sandals girl headed into the cold? Honestly… I don’t know yet! That’s the point.

You’ll watch it succeed or fail in real time, and I’ll be completely open about it either way. If I end up buying emergency boots in Milan in November, you’ll be the first to know (and Milan is not a bad place to have that "emergency" 😉).

The bulky shoe question (hikers, snow boots, the pairs you dread):

So many of you asked some version of: “my trip needs bulky waterproof hikers, and I do NOT want to wear them on the plane. What do I do?”

Here’s my honest answer. First, try the plane thing anyway, it’s the easier option.

But if they’re genuinely not comfortable for a whole travel day, then yes, pack them, and here’s the trick: pack them FIRST. Stuff them with socks, put them at the bottom, and build the rest of your suitcase around them.

What you can’t do is pack them last and hope for the best. Carry-on space is limited. That’s not me being strict, that’s just physics LOL.

When a bulky pair rides inside the bag, something’s gotta give, usually 2 to 3 rolled tops’ worth of space. Knowing that trade upfront means you make your decisions on purpose, instead of discovering it at 11pm the night before your flight.

And ​my carry-on packing calculator​ will show you exactly what those hikers cost in YOUR suitcase, before you’re sitting on it to close it.

Your recommendations: what I bought, what I passed on, and the one still tempting me.

My inbox turned into the best shoe store on the internet this past month. Thank you!!

You understood the assignment: help the sandals girl find boots she’ll actually wear. Here’s what happened with your suggestions:

✅ Bought: Vessi (see above). The crowd was right.

🤔 Passed, but barely: the Thursday Boots Downtown Bootie in Toffee. Gorgeous, and it actually PASSED my every-bottom test. The Quince sock bootie won on one tiebreaker: extra warmth for a colder trip.

That’s a lesson worth underlining: when two pairs both pass the versatility test, your trip’s conditions break the tie.

😍 Still on my list, send help: the Flora Leather Chelsea Boots, recommended by Katherine who is basically a travel boot expert. The cherry red is my favorite. I just need some personal convincing that I am, in fact, a cool girl who can rock Chelsea boots.

I’d also have to see them work with my cashmere skirt and wide leg pants first.

And if you’re a boots person through and through: I haven’t tried Blondo waterproof boots myself, but several of you vouched for them, some are on sale at Nordstrom right now, and waterproof + stylish is exactly the combination fall demands.

📌 One last thing before you go: the shoe chaos, the layering questions, the fall styling tips, the packing strategies, the two climate trips… I’m building all of it into the 🌦️ Shoulder Season Carry-On Style Guide. This is my best work yet! I'm proud ok 🥹

You’ll hear more about it on August 27th. If you want first dibs when it opens, just hit reply with the word FALL and I’ll put you on the early access list.

Thanks so much for being here!!

Now go check your shoes against your bottoms, decide which ones make the cut and pack that carry-on with confidence. You've got this 💪🏼

XO,

Aimara

>>> PS: Next Sunday: travel day outfits. What to wear on planes and trains so you’re comfortable for hours ✈️ Shoulder season is especially tricky for airport looks, but I'll share everything I know next week.

Heading to Italy in the fall? Check these out next:

• ​Best shoes for fall in Italy (organized by region)
• ​Wrinkle-free packing list for fall (2 weeks, 24 outfits, 1 carry-on)
• ​10-day packing for fall in Italy (only Quince items)