Three Things I’d Pack for a Fall City Trip
Two of my fall city trip staples: crossbody bag + walkable boots
When I used to pack for fall trips, I overpacked — trying to be ready for everything: every weather change, every activity, every “just in case we go here” scenario. I thought I was being prepared, but my suitcase was stuffed and I still wore the same handful of pieces on repeat while the rest stayed untouched.
That’s when I realized that packing — and truly being prepared — isn’t about bringing more choices. It’s about packing the right pieces you know you’ll actually wear once you’re there..
These three staples have become the ones I never leave home without for a fall city trip. They’re classic pieces I can wear year after year. They work for walking all day and transition easily to dinner — perfect for trips that tend to lean a bit dressier.
The three pieces I always pack….
1. Crossbody Bag
I always travel with a crossbody bag, and mine is the See by Chloé Small Joan Bag in Caramello (brown leather and suede with gold detailing). I bought it on sale several years ago, and it’s still one of my most-used pieces.
It’s slightly larger than a typical crossbody, which is exactly why it works for travel. It fits my passport, wallet, phone, charger, and even a small water bottle. On flights, it doubles as my under-seat bag — which matters even more now that airplane legroom feels tighter than ever. I like having everything I need within reach without digging around in the overhead bin.
When I choose a crossbody for travel, I look for a few key things: a zip-top closure to keep everything secure, a strap that’s comfortable for all-day wear, and enough room for my essentials without being bulky. It also has to work with my wardrobe. This one does — the brown leather and gold hardware pair perfectly with the camel, brown, and gold tones I wear most. The key charm, braided ring, and mix of suede and leather give it a distinctive look that makes it stand out more than a plain travel bag.
I’ve carried it everywhere — through museums in Greece, sightseeing in London, and to dinner at night. It works just as well with sundresses in summer as it does with jeans and a sweater in the fall.
✨ Secondhand find: This bag isn’t sold new anymore, but it shows up often on resale:
This bag has traveled with me everywhere — perfect for any city and season.
2. Trench Coat
A trench coat is the outer layer I always pack for a fall city trip because it works with everything — from a travel lounge set to denim during the day to a dress and heels at night. You can throw it over almost anything and look instantly put together.
It’s light enough to wear in early fall but layers easily with a sweater or scarf if it’s chilly. On an overnight flight, I put it over my travel set, add sunglasses, and I’m ready to explore until I can check into the hotel.
When I choose a trench, I think about fit and construction. It’s a classic investment piece that should last for years, so it needs to have room for layering without losing its shape. The sleeves should hit at the right spot, and the shoulders need to have enough room to move comfortably. Quality fabric makes all the difference — it should drape well and hold up to years of wear.
My Sézane Scott Trench in Camel. checks every box: it’s cut perfectly, has all the traditional details, and works with everything I pack. Paired with my Joan crossbody bag and ankle boots, it’s my go-to combination for a city day — comfortable, classic, and ready for anything.
✨ Where to find it:
A camel trench coat is one of my three fall city trip essentials-it even makes a travel set look put together.
3. Comfortable Ankle Boots.
City trips mean walking — often for hours and over cobblestones or uneven streets — so a comfortable ankle boot is non-negotiable. My pick is the Marc Fisher Leonna boot in brown leather, a pair I’ve worn on multiple trips.
I’m picky about ankle boots — if the heel is too high or they aren’t comfortable when I try them on, they’re a no for me. A low, walkable heel is a must, and these have the perfect balance of height and comfort. I usually pack these and a pair of sneakers, alternating them throughout the trip.
These boots were perfect for walking all day in London — I wore them from morning sightseeing to dinner at night without a problem. They pair with everything I pack: cream jeans, dark denim, and even dresses with brown tights for evenings out. They come in several colors, but I chose brown because I tend to lean toward brown bags and earth tones, and this shade ties my outfits together.
Walkable ankle boots are a key essential for a city trip — they give you a slightly more dressed-up look than sneakers without sacrificing comfort, so you can enjoy the trip without worrying about your feet.
✨ Where to shop:
Walkable ankle boots — stylish and practical for city days.
Your Turn
These are the three pieces I never skip for a fall city trip: a crossbody bag, a trench coat, and walkable ankle boots. They’re versatile and dependable — the kind of pieces I wear season after season, no matter the destination.
Your essentials might look exactly the same, or you might swap in a favorite blazer, a cozy knit, or something completely different. The goal is the same: pack the pieces you know you’ll actually wear once you’re there.
What are the three things you always end up packing? Maybe it’s a blazer, a scarf, or your favorite travel dress. Everyone’s list looks a little different — and I’d love to hear yours.
✨ Flight 2 Fashion takeaway: Smart packing isn’t about fitting more into your suitcase — it’s about choosing the pieces you’ll actually wear, and making sure they can be re-worn and styled different ways throughout your trip.
✨ Want to put this into action? Download the Three Things I Pack template in Smart Packing section of the [Resources Library] — a simple organizer to define your own three essentials for every trip.
✨ Looking for inspiration? Visit the [Fall 2025 Inspiration Gallery] for destination moods, color palettes, and outfit collections designed for city trips.
