#MissAmyMayInTheUSA: Style On Vacation

We all do it. We picture having a glamorous and stylish vacation during which we sport a new polished, put together outfit every day so we look groomed and pretty in all our holiday snaps. We think we will have ample time and energy to spare for putting in a wetset in the evening, or for creating an elaborate up-do on the morning after we’ve found 40 minutes to paint on a perfect pinup face. We think we will be able to handle the heat without changing our style or schedule at all.

We dream, basically. It’s a fantasy. Props to the people who manage that, because normally I’m not one of them. I have had the same fantasies about every vacation I’ve gone on since I’ve become a pinup, and while I normally manage to make at least some effort it’s never been the full force I’ve hoped for. And typically the chance to take outfit pictures has fallen by the wayside too.

So while I’ve done a full October run down of the month’s outfits as usual from last month  including the October portion of my trip to America, I wanted to do a post that focuses particularly and honestly on what I wore while I was away, how I adapted my style to being away from my full wardrobe and vast collection of beauty supplies, and how my energy levels and motivations held up against the fantasy expectations of looking perfect and primped every day of a 15 day vacation spent in two different locations.

It began well. I wanted to be, for the first time in my life, one of those people who looked good on a plane, not my usual make-up free air-traveller in yoga pants and a ponytail. I obviously needed to still be comfortable, even if I did want to look decent, so I chose my super stretchy and comfortable Collectif Dolores dress. I threw on my most-worn and cute flats, my red bedazzled flats, and a cardigan and seamed tights. The Tatyana London Trench coat finished off the practical aspect of my outfit with polish. I wore my hair in pincurls to the airport to give them a little extra time to dry, then brushed them out in the dim morning 7am light in the car in the drop off parking outside the terminal. I woke up an extra hour early to do my makeup and pack it all into my luggage before we left.


It was a long travel day and I was exhausted by the end of it, but jetlag meant I only got 2 hours sleep that night. We were going to spend the day travelling to the next town, touristing it up and then going to the rehearsal dinner, so I needed to be comfortable but also presentable enough that my hair and makeup could transition to the events of the evening with only a minor touch up. I clipped in the braided faux bun I had bought before my holiday for days when I might be low on energy or time but needed to be presentable. First full day of the vacation and it was already getting use. Good or bad?


So for the evening I powdered my face, added the red lipstick I couldn’t be bothered to touch up throughout the day, and changed into my Pinup Girl Clothing patriotic Amanda dress to represent both Britain and America for a little fun.


The third day of my trip, Saturday, was the day of the wedding, the day I was most excited to glam up for. With my jetlag in full force, though, already my motivation was fading somewhat beneath my tiredness. I meant to wash my hair on Friday night after the rehearsal dinner and set it overnight in sponge rollers in clip in extensions. At 10 at night, with the bad sleep debt I was already amassing, I couldn’t face doing a wetset. Instead early on Saturday morning, after another very short night’s sleep, I showered and used my pincurl sculpture tool to set my hair into tight pincurls, knowing that meant I would have short and bouncy hair for the wedding rather than the glamorous, longer set I had envisioned. I threw on my Voodoo Vixen Joni dress, a red cardigan and a headscarf to go to breakfast with my friends, then came back to the room to help my hair along with a short blast of the hair dryer. By wedding time at 5pm, this was my full outfit.

I wore the Chi Chi Clothing Cassandra dress, my own handmade bedazzled heels and clutch bag, a vintage crystal brooch, a faux fur shawl from eBay, and a crystal bracelet from Primark.

The following day was my last day in Virginia. I threw on the Collectif Nautical Ginger dress for another makeup-free breakfast with my friends then packed up everything to leave. My flight to Texas was at 6 in the evening and would be arriving at 9.20pm, so I wanted to be comfortable all day and during flight. I was tired and my hair was a mess of odd curls from the night before, but I wanted to look at least somewhat decent for the pictures I knew would be taken when I met Sarah at the airport. I put my hair up into a messy poodle do, fixed it under a bandana, and added a cardigan and my trusty red flats to the aforementioned Collectif dress. I couldn’t be bothered to take pictures of my outfit for documentation, so middleground was my motivation.

My first day in Texas I was super tired and not in the mood to get dolled up, so when we went out for my first Southern breakfast that morning it was a bare makeup and low effort day. The only picture I have from it is this gleeful first selfie with Sarah taken in the back of the family truck as we sped towards biscuits and bacon.


We went to the mall on Monday and to be honest I have no memory of what I wore. I think I did full pinup makeup, but I don’t remember? My jetlag meant I was now snagging maybe 5 hours of sleep a night but after 5 days of sleeping hardly at all, so my sleep debt was massive and it was wearing on my ability to be enthusiastic about my appearance.

Tuesday was the first day I returned to my full pinup self in Texas to do our first photoshoot for the blog. My hair was set, I did my makeup fully and I wore something cute.


Wednesday Sarah and her sister Rachel took me to their local swing class, so we decided to be sickeningly adorable and wear our matching Pinup Girl Clothing Ella dresses. My brush out had gone a little limp during the day so I pinned most of it back loose and low on the back of my neck. I wore my red bedazzled flats, as always, because they would be comfortable for dancing, and added the Ice Blue Cropped Cardigan from PUG as it was a bit chilly. Sarah and I decided to be cheesy prom dates for our midnight post-dance outfit picture.

When we went to Walmart and Target I threw on one of my other dresses I knew would be comfortable, the Collectif Penny flared dress, with cardigan and flats as usual. I had bought 3 pairs of heels with me to America and so far had only worn one pair once for the wedding. Shocking? No. I’m an over packer, but I had been selective about only bringing cardigans and flats that I knew would work with multiple outfits and so far that was panning out just as I’d expected. I brushed my hair out from the night before and pretended it would suffice, since I’d bothered to do my makeup, false lashes included. When it came to the makeup it was full force or barely any.


For another day out pottering around for lunch and stuff I kept up the outfit momentum with the Pinup Girl Clothing Harley dress. I did my makeup fully but could not be bothered to make an effort with curling my hair, since I was recovering from the jetlag by the but still too tired to want to set my hair at night, so I went the lazy route with a bun, although a real one and not my clip in I’d used before.


By this point I’d lost track of the days but was managing to scrap together some energy to keep it cute when we went out, as we did on FRI wore out my Collectif Sherwood dress with a cropped Cardigan from Unique Vintage, copped out with my fake bun yet again but kept the false lash game strong. Makeup was still being fully applied.


On Saturday, Halloween, Sarah and I spent the afternoon playing models for a local photography group, so we met them with 3 outfits each in tow and hair and makeup perfectly done. The humidity saw our pincurls drop in frustrating record time and we switched between set ups and photographers every 3 minutes for 2 hours, drawing on my prettiness energy pretty heavily. Once we were done all we wanted to do was eat and get home into our comfies with no zest left for Halloween celebrations.



Picture courtesy of Ed Wasson Photography

My only Sunday in Texas was spent at the Forth Worth stockyards, followed by lunch, a bubble tea outing, a trip to the Botanical gardens and the water gardens. I’d been on vacation for 11 days by this point but had conquered my jetlag, so I wanted to take pictures in the closest approximation of a pinup cowgirl outfit I could muster with what I had bought with me. I wore my Bernie Dexter Chrysanthemum print Paris dress with a cropped cream cardigan that matched my new cowgirl hat presented to me by Sarah’s family. We took a full set of pictures at the stockyards, then again at the Botanical gardens, so by the time we got home I was knackered and yearning for my pyjamas something fierce.


I was loving my time away but after shooting another couple outfits for the blog on our off days from gallivanting around Dallas–I lazied out and wore my hair in a bun for those shoots, something I had never done before as I always have pincurls for my shoots–I was spent and more than happy when we got to laze around for a full day in sweats.

For a day at the Zoo it seemed like the weather might be hot so I didn’t want to wear anything heavy or even, gasp, my beloved petticoat. I threw on the Doll Me Up dress I had worn the week before with a new colour cardigan and a vintage brooch Sarah’s mom had gifted me the night before.


The next day all my pretty energy was funneled into shooting a The Pretty Dress company dress for the blog, the only time I was aware that I put in my clip in extensions and set them fully.

It was drawing close to the end of my vacation. On the last Wednesday night Sarah and I donned our Pinup Girl Clothing Monica dresses and went out for dinner as an in-lieu-of-our-birthdays celebration together.

On Thursday Sarah got sick so we spent our last two days on the sofa together in sweats, messy haired and makeup free. I had expected to fly home in something just as cute as I had worn on my last two flights, but tiredness, laziness and the desire to do whatever I could to increase the likelihood of my getting any decent amount of sleep on my overnight 9 hour flight home to the UK prevailed and I threw on a t-shirt, hoody and yoga pants. Yes. I was all out of glam. We lugged my 3 suitcases of beautiful pinup duds to the airport, I cried a bunch saying goodbye to Sarah and her clan, and I arrived home in England looking like a thoroughly average normal.

Looking back at it as this style diary, I spent more time making an effort on vacation than I thought I did. We had days off at home just relaxing together which I needed not only to enjoy my quality time away with Sarah but also to recharge and feel like I had any energy at all to get pinned up the rest of the time. When I’m at home in England I get dolled up only 2-4 times a week as I can’t get pinned up for work and those are the average number of times a week that I’m social. Only getting to dress up a few days a week keeps the process enjoyable and fun for me. I’ve always known that if I had to do full vintage hair and makeup everyday I would probably struggle with the energy it takes, for the hair especially, as I’m not gifted in that department, so I found it interesting viewing this vacation in the sense of that being an opportunity to get dolled up every day. I didn’t want to. I wanted and needed days off. Some people may think that means I’m not a ‘real’ pinup if I can’t handle it on a daily basis and don’t want to, but to me I dress this way because it’s something enjoyable that allows me to express myself.

There are facets of me that are lively, glamorous, exaggerated, outgoing and dramatic. But I’m also a little shy, sometimes quiet, happy to be alone, introverted, chilled and a homebody. Dressing up expresses the louder, twinklier aspects of myself, but having days when I slob around in sweats and no makeup gives me time to recharge and gather energy for what’s coming next, to unwind and to enjoy being grounded as much as I enjoy being overdressed. Those are opposing but equally present sides of my aesthetic and personality, and I make no apologies for either of them. And neither should you.

So if you want to keep your pinup style polished and on point when you’re on vacation, I hope this style diary shows you that it’s possible if you pack well and give yourself time to prim. But if you can’t be bothered, if you want to enjoy your time away in the most relaxed fashion possible without worrying how your lipstick is holding up, I hope this shows you that’s just as acceptable. Vacations are for living and enjoying, the same, I would like to think, as we should live every day of our lives. Do whatever makes you most comfortable and happy.

15 thoughts on “#MissAmyMayInTheUSA: Style On Vacation

  1. Ugh vacations are so exhausting! Isn’t that weird? It’s supposed to be relaxing but it’s also nerve-wracking – especially if you’re traveling. You’re right, you have goals to be floating about looking all perfect and then you find the opposite happens. In the end, you looked great no matter what you went out in and the most important thing is that you loved your trip! =D


  2. I’m actually in awe of just how much you packed in and how gorgeous you looked despite the horrendous jet lag!! When I travel I pack light (separates rather than dresses), wear little makeup, and use hats to hide my hair! What a trip! X


      • True, but many fashion blogs, including the subset of pinup blogs, seem to show only the shiny, perfect side of things. I try to abide by the phrase “it’s not all glamour” and show more day to day stuff on my blog, and I like that you’re honest and down to earth in your blog 🙂 It’s one of the reasons I so enjoy reading it


  3. That’s way better than I ever do with traveling. Of course I haven’t really transitioned to pinup style every day in any aspect, and I probably won’t, although I’m trying to lean more that way. I HATE packing especially because I like to have options, but I don’t want to carry around all the options with me. But I was like that even before I started dressing in pinup style.


  4. Thank you for saying you struggle with pinup hair! That is by far the hardest part for me, and it drives me crazy when my hair won’t do what I envisioned! You’re one of my favorites to follow on instagram and it gives me hope that I can look as polished as you and still get frustrated with my hair! 😀


    • That’s so sweet, thank you! I’m glad I can keep it real and help assure you that pinup hair is hard to get the hang of, that plenty of people you admire it on aren’t naturally gifted at it, and that everyone is always learning with it. It’s like makeup. It’s a constant learning curve of picking up different tricks and techniques.


  5. Pingback: #MissAmyMayInTheUSA: Things I Learned In America  | Missamymay

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