If you know me, you know I’ll drop anything to travel to Japan at the drop of a hat. I lived in Tokyo for over two and a half years combined, and honestly, I’m itching to move back every day. The food, the sights, the fashion… Tokyo is undoubtedly my happy place. So, when my now-fiancée surprised me with a trip to visit during cherry blossom season with two weeks’ notice, my internal alarm bells went off. I knew that every look I wore for our impromptu trip had to be perfect.
Naturally, as a Virgo Moon, I went into full panic. For days leading up to departure, I frantically packed and unpacked my Rimowa suitcases full of clothing. Satin dresses, white mini skirts, luxury bags, and high heels were all part of my original rotation, meticulously clipped together and documented in several spreadsheets and styling PowerPoint presentations. My Close Friends story on Instagram saw not one, not two, but three unhinged instances where I uploaded several looks in the pursuit of capital F Fashion.
After consulting with a few stylist friends, they all advised me on the same thing: When traveling, especially for an important occasion, it’s best to wear clothes that you feel comfortable in. Traveling is for taking risks, but not the sartorial kind. I then applied the newfound nugget of wisdom to my recharged packing philosophy. Instead of focusing on what I thought I would look good in, I packed what I knew I would feel good in. Think comfortable barrel-leg jeans, voluminous skirts, and cozy knits I could explore Tokyo in. Their consensus was right—my emotions came first and my outfit second, something that, looking back on, I’m incredibly glad I did. I was able to enjoy my trip and our special moment without worrying about how I would look on one of the happiest days of my life so far.
Now that I’m back in New York with a suitcase full of vintage treasures from Shimokitazawa (and an engagement ring to boot!), I can safely say my packing skills are much better than before. And so is my ability to focus on what matters: the memories, not necessarily just the outfits. Below, scroll through to see all of the stunning spring items I packed in my suitcase for Tokyo.
A barn jacket is always a good idea.
Aligne
Natalie Elasticated Cotton Midi Skirt
For an easy, carefree springtime look, a white cotton skirt is a no-brainer.
Bottega Veneta
Long Andiamo Intrecciato Leather Clutch
I have to admit that I’ve been holding onto this bag since last summer. She finally made her debut for my bridal era, but overall, white purses just scream spring and summer to me.
This red polo layered with black pants made me feel like a million bucks. Plus, it’s so easy to style.
Prada
Medium Brushed-Leather Tote Bag
Prada is always a good idea.
Mango
Long Semi-Transparent Cape
Listen, I know this cape might be a bit impractical, but when I wore it with a simple white tank and straight-leg black pants out to dinner, I quite literally got stopped in the streets of Kichijoji by a local to ask where it was from.
Heaven Mayhem
Sloane Black
Now that these Heaven Mayhem sunnies are for sale, I’m proud to say I’ve been swooning over them for months. After sporting them across New York City, I knew I had to add these to my Tokyo suitcase.
Afrm
Ettie Essential Pant
Yes, I can confirm that capri pants are still majorly in for 2025.
Mirror Palais
Double Cowl-Neck Drop-Waist Silk Chiffon Midi Dress
Okay, this might be embarrassing to admit, but the second I heard about the trip, I had a feeling I would be getting engaged. I texted a dear friend of mine who was able to get her hands on this Mirror Palais dress as a gift for me, courtesy of Anthropologie. While this drop-waist silk chiffon dress might scream bridal to you at first, honestly, it’s perfect if you’re looking for a formal springtime frock. The open back detailing and neck scarf take it from simple to absolutely stunning.
The reason these shoes are ideal is quite literally in the name—everyone in Japan is wearing the new Adidas Tokyo silhouette.
Relax Lacrosse x Lisa Says Gah
Bows & Rose Lacrosse Pants in Red/pink
Dissh
Abigail Black Hybrid Long Sleeve Midi Dress
I like to throw in a simple, black dress while traveling because it works for every occasion. This easy to pack (and practically wrinkle-proof!) Dissh dress was perfect to wear over and over for all of the celebratory omokase dinners we had.
Mango
Linen-Blend Knitted Sweater
Haven’t you heard? Powder pink is the color of the season.
Frankie Shop
Pelly Trench in Sage
Everyone already has a classic khaki trench in their closets, but do you have a cool greenish-gray one? Probably not.
It’s the little things in life.
Anthropologie
Pilcro Oversized Washed Faux-Leather Jacket
So many Who What Wear editors have this classic Pilcro oversize leather jacket and, frankly, for good reason—it’s so easy to wear come springtime. Simply pair with jeans and walk out the door.
Lioness
Leisure Stripe Long Sleeve Cotton Polo Shirt
This striped rugby shirt is one of Hailey Biebers’ favorites.
Madewell
Straight-Hem Button-Up Shirt in Suede
I’ve never seen a Madewell piece I didn’t like.
This sweet little neck scarf is the ideal accessory to pack when you’re traveling somewhere new in-between seasons. Wear it as a bonnet! Wear it around your neck! Wear it as a pocket square! The options are endless.
Mango
Polka-Dot Wrap-Neck Blouse
Can you tell I have a thing for pretty chiffon neck scarves at this point?
Aligne
Markus Barrel Leg Jeans
If you’re going to buy anything from this list, let it be the classic barrel-leg jeans from Aligne. No joke—I have these in three different colors, but this classic medium wash is the one I travel with the most.
Vivaia
Lightweight Pointed-Ballet Flats
These shoes are made for walking–literally. Given my insane 20,000+ step count, I’m shocked my feet didn’t fall apart. Honestly, I owe it all to these ultra comfy, stylish Vivaia flats.
Almina Concept
Wool V Neck Sweater
Okay, this sweater looks rich. It’s always my go-to when I’m heading on a long flight but still want to look like an off-duty Miu Miu model.
Sandy Liang
Thong Mule 60 in Optic White Nappa
These pretty bow thong mules from Sandy Liang might have been too on-the-nose when I packed them, but honestly, I’m glad I did—they were adorable in all of my pictures.
Madewell
Studded Western Belt
Zara
Structured Knit Polo Jacket
Every spring, butter yellow hues enter my lexicon, and honestly, I’m all the more stylish for it.
Mara Hoffman
Bateau Neckline Long Dress
Everyone needs a pretty drop-waist dress for the spring. While I scored this red Mara Hoffman dress years ago during a sample sale for the brand, you can find this one on The RealReal for a steal of a price.
Aritzia
Homestretch Rib Crew Longsleeve
If you’re looking for the perfect white tee to layer with this spring, look no further.
Jenny Bird
Estelle Rope Necklace
Jenny Bird never disappoints, and this chic pendant necklace is a clear winner for spring jewelry staples in my mind.
Eloquii
Flowy Bow Detail Maxi Dress
This pretty Eloquii dress was my strong runner up when it came for my engagement pictures. While I didn’t wear it on my trip, I know I’ll be putting it on every chance I get as I enter this new chapter in my life.
