The most important outfit of your trip is the one you wear to actually GET there.

Think about it... it's the longest you'll wear any outfit all trip.

The 4am alarm. The freezing airport. The overheated train. The airplane that's somehow stuffy AND arctic at the same time.

And in shoulder season, there's an extra twist: you're usually leaving one season and landing in a different one. So many of you told me exactly this. Leaving warm, landing cold. Leaving cold, landing warm. Long train days between climates.

So today we're solving travel day outfits. And I'll show you exactly what I'm planning to wear on October 13th, when I fly to Italia.

The one rule that solves every travel day:

Dress for the colder of your two places. Peel down to the warmer one.

And here's the trick that makes it work: whatever you're wearing at the very bottom has to be an outfit on its own, because that's what you'll be standing in when you land.

Planes and train stations are cold, hot or both. Arrivals are unpredictable, and layers you can add and remove will always beat one "perfect" outfit. The only thing that changes is which direction you're peeling:

☀️ Leaving warm, landing cold?

You're dressed for the cold side, you just don't pile it all on until you land. Build from the inside out:

✅ A merino base layer, the thin long sleeve that goes under everything (remember ​the layering email​?). It regulates your temperature, so you won't sweat at the gate while dressed for your freezing destination.

✅ A cashmere sweater over it.

✅ Stretchy bottoms you can sit in for hours: Ponte pants are my favorite (they look polished, are very comfortable and you wear them at your destination). If your trip is less than 7 days wear anything you want (this is Spanx Air Essentials territory) and if the trip is longer make sure at least 2 pieces work at your destination.

✅ Shoes: it depends. If you're packing comfy booties, wear them that day. (unless they fit in your carry-on, but I know this is not usually the case)

✅ Your coat, beanie, and pashmina ride in your personal item until you land. You do NOT wear the puffer through security. Ask me how I know 🥵. For fall trips, your puffer should fit. I'm bringing this packable one with a hood.

🥶 Leaving cold, landing warm?

Reverse it: underneath it all, you're already dressed for your destination. The warm layers are just the wrapping, and you unwrap yourself when you land.

✅ A soft tee or base layer that IS your landing outfit, already on. Merino T-shirts or tank tops are great because again, they regulate temperature and add ZERO bulk.

✅ An easy layer you peel off the second you arrive. (like a cardigan)

✅ The coat: you won't need it on your trip at all, only for getting to the airport (and getting home, remember you land back in the cold). So this decision is 100% about your ride. Public transit means the coat is coming with you (sorry), so leave room in your personal item to stash it once you're inside. Getting dropped off at the door, skip it. (and if it's a big coat and no space to spare... that's the Chicago-to-Caribbean problem. I'll get to it at the end of this email)

✅ Sneakers on your feet, sandals in your bag. Totally optional to have the sandals in your bag and change at the airport upon arrival.

🚂 And for my train travelers:

Everything above still applies. But trains add a twist: YOU carry your bags, everywhere.

Up the platform steps, into the rack, back down at your stop, sometimes with 4 minutes to make a connection.

Your travel day outfit needs to move with you: nothing tight, shoes that grip, and every layer you might shed needs a home in your day bag.

A train is not the place to be holding a puffer, a pashmina, a personal item, a giant bag and a ticket while finding coach 7.

Also friendly reminder, this is the #1 reason why I travel with carry-on. Not to skip the bag carousel, but to be able to handle my bag with ease during my entire trip.

⚠️ How about athleisure?

Without a doubt, the most comfortable you'll ever be on a travel day. But for longer trips, it shouldn't be your default, and here's why: those sets are bulky. SO bulky.

On travel days they're great, but every day after that, they're a big soft space thief you have to pack and unpack at every stop (given you're not wearing it of course).

I do own one set that earns its space (nothing beats Spanx Air Essentials, but this one packs down way easier): it's comfy for the flight, cute enough to rewear, and it doubles as loungewear, which a long trip absolutely requires ⬇️

What I’m planning for October 13 (Phoenix to Milan):

✈️ My travel set: so many of you recommended it that I finally went for it. Comfy enough for 12+ hours of travel, cute enough to rewear all trip. (I have it in black)

It's actually a 3 piece set, but I think I'm leaving the cardigan behind: it's not warm enough for Milan in October. I'll be wearing this cashmere cardigan instead.

✈️ My Vessi sneakers, because if it's raining when we land, I refuse to start my trip with wet socks.

✈️ My new travel scarf rides in my backpack. First time trying it instead of my usual pashmina, and I'm excited. I got it in olivewood.

✈️ My puffer won't be needed on the travel day itself, but it rides in my carry-on just in case Milan greets us with attitude. Taxis are EXPENSIVE in Italy, so I already know we'll be getting to our Airbnb using public transportation. Don't forget that sometimes your travel day doesn't end when you land.

✈️ Bombas compression socks, non negotiable for long flights ever since my feet swelled up flying to Asia earlier this year. It'll be my first time wearing compression socks. Turning 39 is going great 🤣

And the trick holding the whole system together: my personal item stays half empty on purpose.

Every layer that comes off needs somewhere to go. And what's in my personal item?

💻 Laptop

🎧 Headphones

🧣 Travel scarf

🔌 Chargers

💧 Water bottle

👜 My crossbody, with my passport and phone (it slides inside the backpack when it's time to board, because you're only allowed 2 items)

🧖🏼‍♀️ Antioxidant balm (in case there are smells - or if I'm not wearing makeup, I'll apply some mid-flight)

And the rest? Empty on purpose. Every layer I peel off during the day has a home waiting.

I do want to end it with this...

When home and your destination have wildly different climates, like leaving Chicago in the middle of winter for the Caribbean, there will be moments where no outfit is "right."

I've seen countless Canadians & Americans in Mexico in the middle of winter carrying a giant winter coat through the heat. There's not much you can do about that one.

Just know you can always change the minute you land. Have that landing outfit ready at the top of your personal item, be as comfortable as you can in between, and keep your bags light!

Hope this was useful and thanks so much for being here!!

XO,

Aimara

>> PS: I know I said the Shoulder Season Carry-On Style Guide would be ready on August 27th, but I miscalculated... I think it'll have to wait until September 10th. I'm sorry if this will affect your trip. But please know that you can reply to any of my emails and I'm happy to answer ANY packing questions.

If you're interested, reply with the word FALL if you haven't already, and I'll make sure you're the first to know. If you have any shoulder season packing doubts or requests, send those over too, because I can still add them ♥️ I truly want you to succeed at packing light no matter the trip!

(I'm with family for 2 weeks, so I'll be slow to reply, but I've got you!)