Relocating: How Do I Choose the Clothes and Accessories to Bring?

Hello Akaisha,

I am now a few months from taking the leap of faith and retiring while I still have energy and a dream. I saw my mother wither away after my dad died…she never traveled again!

I think I will be ok moving to Mexico as my home base and going from there. Although I am not quite ready to be a world traveler like you and Billy, I do know that that I am a traveler at heart and need to move to a place where I can afford to live and travel. I do need to make some decisions about clothes and accessories (shoes are my biggest vice).

How did you choose, what did you choose or did you do a clean sweep and got rid of everything? What do regret not keeping?

Would love your advice.

Ours is a casual lifestyle. Here we are in China!

Your friend,


Hi Elizabeth!

Thanks for writing and Congratulations on your upcoming new lifestyle!

I must admit that our transition to being “homeless” and traveling on a more-or-less constant basis wasn’t as smooth as one would think. Initially we sold about 95% of our stuff — and because in 1991 this idea of financial independence and early retirement was all new and I had no clue as to what it might turn out to be — I saved a good deal of my working clothes, shoes, bags, scarves and accessories.

Looking back, I should have sold or donated that stuff and if I found myself needing to work again, just spend $1,000 to get the basics and start over.

Boating in Laos. No high heels here!

What happened was that styles changed, my body shape changed, and things like high heels — for me — were not the kind of shoes I could navigate in on cobblestone streets and broken sidewalks. I had gorgeous snakeskin and eel skin bags and matching shoes — which, since I kept them — simply dried out without the joy of my wearing them to death.

My gallivanting lifestyle simply didn’t require this upscale sort of dressing anymore. It took me a very long time to let go — I hate to admit it — because I loved these classic items and always thought “someday…” For me, it was a fantasy that never made it into reality.

Don’t be surprised if in your new life, nothing will work quite the same way as it does in your native city or town. I can’t tell you how many times I wore my LOUD NEON and bright floral California clothing that looked SO FINE in California or Hawaii, but was simply out of place or made me a target in a colonial city in Mexico or South America.

Bare footin’ in Phuket, Thailand

Or, wearing gorgeous pastel yellows and corals in NYC which thrives on blacks, grays and leather. I wore cutsie cork colored open toed shoes in rainy climates which the mud totally destroyed or beautiful jeweled sandals while walking on the shore to the next beachfront restaurant while the waves lapped over my feet and the sand ground in between my toes… silly stuff!

Another difference in my lifestyle — but perhaps not your new one — is that we, by choice, don’t own a car. That means we go from the front door of our apartment or hotel room and walk to the Plaza to get a taxi or grab a bus or — depending on which country — jump in the back of a small pickup truck or hail down a tuk-tuk. Comfortable shoes are a must in these situations. Often I will join dinner parties where the women there have gorgeous, delicate, high end shoes on – but they have come from their front door, to their car, to the front door of the theater, fundraising event or restaurant.

They have a different mode of living and it’s all good — it’s just that I would hate to have to own a car to support my choice in footwear.

Walking down the gravel trail to the airplane, Laos.

Scarves and faux jewelry can be purchased in your new location. Those items are affordable and will “update” anything basic that you choose to carry with you from your previous lifestyle.

My strongest suggestion would be to choose bags and shoes that are the most comfortable, the ones that will go with the most outfits you own and then pick one or two things that you just “must have and can’t live without.” Remember that practical is paramount and keep whimsical shoes for special occasions.

Of course, all of these choices are up to you and the important thing is to be happy.

I know I’ve told you this before, but I am very lustful of your Zebra striped high heels and if you choose to leave them behind, please mail them to me. I promise you can borrow them anytime, but you might have to come to Cambodia or Nicaragua to get them! 😉

Every good thing to you, Elizabeth, and thanks for keeping in touch.


Don’t be pushed by your problems. Be led by your dreams.

About Retire Early Lifestyle

Billy and Akaisha Kaderli retired three decades ago at the age of 38 and began traveling the world. As recognized retirement experts and internationally published authors on topics of finance and world travel, they have been interviewed about retirement issues by The Wall Street Journal, Kiplinger's Personal Finance Magazine, The Motley Fool Rule Your Retirement newsletter, nationally syndicated radio talk shows and countless newspapers and TV shows nationally and worldwide. They wrote the popular books The Adventurer's Guide to Early Retirement (Your Simple Path to FIRE) and Your Retirement Dream IS Possible.
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