Heels to flip-flops: Turning From Working Professional to Travelling Tramp

Not looking like a homeless can get difficult when you become a full-time backpacker! All the budget lady travelers know that those photos they show off on Instagram just aren´t real – and if you weren´t aware of that, this post is about to shatter some of your illusions. I am sharing with you today the first guestpost on this website, written by talented Sarah from The Whole World Or Nothing where she shares her transition from an elegant manager to a carefree adventurer, even if that means having greasy hair most of the time – and why this change is for the better.

Heels to flip-flops: How I Turned From Working Professional to Travelling Tramp!

Prior to setting off travelling the world I held down a successful job as a middle manager in an office environment and my daily attire was expected to be stereotypically professional and smart. Refreshingly in this chapter of my life there’s no dress code anymore.

You see, travelling holds no expectation of how you should look to others. No one judges your capacity to navigate a new country or attempt a new language based on what you are wearing and whether your hair is styled that day, right? So in the six months since we left the UK and set off to see the world my appearance and my attitude to it has changed somewhat…

Goodbye, pumps!

Probably the first thing to change was my heels going.

Being quite short I used to wear them all the time in the workplace because I felt like the extra couple of inches gave me more confidence. Instead, these days I’m living in flip flops, trainers or bare feet and I’m doing just fine with my authority.

Additionally, I’ve also taken to not wearing a bra most of the time. It’s just so bloody hot and not having much to write home about in the boob department it’s much more comfortable without the restriction! Next came the baggy ‘traveller’ trousers, since purchasing them in Argentina, unless I’ve been on a beach, I pretty much haven’t had them off. They are so comfy and the pattern on them hides the muck well too so it’s a win-win situation.

No washing machine – no problem

It’s funny how quickly it became perfectly acceptable (after doing the sniff test of course) to wear clothing multiple times before washing. I’m less of a fan of wearing underwear twice but on occasion not having washing facilities on hand has dictated the necessity for the old 2 days in a row pant reversal wearing.

Bad hair, don´t care

My hair bands are an absolute necessity for covering up greasy/unruly hair. I have a red and a blue one and pretty much never have them off my head – unless I’ve just washed my hair.

However, as I don’t have a hairdryer or straighteners with me I tend to avoid this until absolutely necessary. I did bring a limited supply of dry shampoo with me but this soon ran out. Another personal hygiene boundary that I’m pushing is hairy legs, bits and pits.

Now this isn’t out of choice and not constant, I just shave less often because invariably when you are staying in budget accommodation the showers leave something to be desired. It’s often not the most enjoyable of experiences so I tend to be in and out as quickly as possible.

Smiles in Chile.
Smiles in Chile.

Make-up? Not today!

In fact the whole ‘getting ready’ routine takes a lot less time in general. I’ve tended to wear less make up as I’ve gotten older anyway and typically none on weekends just spent at home. But you would have never caught me going to work without it on (apart from the one time I left it on my desk the day before, „how embarrassing!“ – I remember thinking).

Now, a few months in I just don’t wear it, I’m getting used to my face without it and my self-esteem is doing just fine. Having some time on my hands these days I recently decided to experiment with my hair colour too and try going blonde.

There are of course hairdressers in South America but not wanting the expense, I bought a hair dye and gave it a crack. It wasn’t quite a success in the desired colour outcome and was kind of patchy ginger but I wasn’t fazed. Who cares, right?!

Definitely not the traveller next to me on the long haul bus who also hasn’t washed for 2 days. Contrastingly, had this been 6 months ago I would no doubt have called in sick the next day whilst frantically calling all hairdressers in the area to get an appointment!

Back to the old ways?

Don’t get me wrong; there are days when I’m feeling super crappy and I wonder if being at home and being able to have a good groom, make myself up, whack on some killer heels and strut my stuff would make me feel better. However I don’t think it would have the effect it used to. You see, my confidence has increased anyway since starting travelling and I’m sure my attitude to my appearance is a large part of that.

I don’t think that anyone close to me perceives me any differently, least of all my husband. In fact asking him, he says all he notices is how much happier and more comfortable I am with myself. Naww! As for people who don’t know me I’m not sure I care what they think of my appearance (there was a time I did, very much) and anyway these days the first thing someone probably notices about me is the huge smile on my face – not that I look a tad grubby!

All of this does however leave me wondering how I would fit back into the expectations of the corporate world if indeed I will ever want to. Sure, I could rebel against the system and rock up to an interview in flip flops, baggy trousers, a vest that hasn’t been washed in 3 days and unkempt oddly dyed hair but I’m not sure that would land me the job. Anyway, those decisions are a while away yet hopefully. I have too much of the world to see first.


Sarah x

Giggling away in Argentina.
Giggling away in Argentina.

If you’ve recently returned from travelling to the corporate working world – how have you coped with the expectations on your appearance? Any tips on the transition?


Don´t forget to follow Sarah and James´s stunning photography and adventures on Instagram, Twitter and Facebook !


Pin it for later!
Pin it for later!


  1. Bee

    Hahaha NO BRA 😀😀
    I travel a lot but it all depends on where I’m going and why. I can definitely relate to no make up and really sometimes no shower.
    I got used to no washing machine.
    I was in Dubai for my last travel and it doesn’t get more corporate than that.

  2. This is great! The same thing happened to me when I was in Nepal. I was only there for a month, but it was in the middle of winter, and we didn’t have a shower – just a tap and a bucket! So washing was a shiveringly cold experience that was endured as little as possible! Now I’m living in Japan, and its a very different vibe – everyone always looks so smart! But I’ve recently tried to relax a bit more again on my days off from work, and go back to my flip flop/ trainers, shorts and t-shirt wearing habits 🙂

  3. I completely relate to this – so so much!
    I actually feel more comfortable while rocking my “travelling tramp” look. It is probably because I have had more time being a backpacker or in environments where I could dress casually over dressing “professionally”.
    I guess I am fortunate enough to have a job and a professional background that allows me to be a little more relaxed about my appearance! At the moment I am travelling in Vietnam, and I am currently working as an English Language teacher in Hanoi. We dress nicely but I can still get away with no heals, no make-up, and no pant/skirt suits if I don’t want to! Lucky me 🙂

    • That sounds really nice! I worked as a teacher in Colombia, but we had (ugly) uniforms, so no comfy clothes allowed. We didn´t have to wear heels though, flats were fine, but the uniform itself was horrible – long skirts and weird unfitting blouses, yuck.

  4. I found myself relating to a lot of this. I can’t be bothered carrying around dry shampoo but I find talcolm powder a cheaper and easier to find option. Anything to delay having to wash the hair!

  5. Haha this is so apt, it is truly hard to keep up appearances while travelling and everyone arounds you just accepts how you look so I think we all let it slide 🙂 Most memorable for me was 2 weeks sleeping in a car on a roadtrip- wasn’t looking too good at that time!

  6. I love this. It is exactly how I have felt after leaving corporate. No bra, no makeup, no worries haha I don’t know how I will ever part from my harem pants back to business attire but I will cross that bridge when it comes. 🙂 Thanks for sharing

  7. Sheena

    Of course I wouldn´t wear makeup if I was traveling like this, but I wouldn´t survive life without it… but that´s because I love make up, I love doing it, and it´s my hobby and therefore part of my personality…. But what I´ll always be anvious about is the option not to wear bra at all… I so wish I could do that! but that unfortunately there´s no chance for me in this way:( 😀

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