Ever since I watched Grease as a child, I have been enamored with vintage fashion. Growing up, my love for retro garments evolved even more, so I thought it would be incredibly fun to spend a week dressed in 1950s teen fashion. My love of vintage style — particularly the fashions worn by American teens in the '50s — stemmed from Grease 's leading lady Sandy. As a total adolescent goodie two shoes, I could really relate to her. The fact that I was blonde and always wanted to be a cheerleader probably helped. I adored everything about her style: Her ponytail complete with a ribbon, her preppy cheerleader uniform, her prom dress, and the foxy outfit that she wore in the finale.
Being a teenager in the '50s always seemed like a dream to me. TIME Magazine even called these youngsters "America’s luckiest generation," because they were "beneficiaries of the very economic collapse that brought chaos almost a generation ago," as outlined by LIFE in 1954. Granted, this was mostly applicable to "white working- and middle-class teens." Similarly, the BBC expressed, "During the Second World War a new group of people had emerged — teenagers. In the 1950s, young people had more money and leisure time than ever before." It was a time when rock and roll flourished and Rebel Without A Cause exemplified the way teens of the '50s were beginning to change their narratives.
And so I decided to dress like a '50s teen for a week in the hopes that I would get a feel for what it was like to grow up in this incredible decade. Here's how it went.
Day 1: Monday
I began the week by dressing in one of my favorite outfits from the wardrobe of my vintage girl band Diamond Darlings. We love sporting our polka dot dresses with underskirts and peep-toe shoes as we sing songs by The Andrews Sisters and Marilyn Monroe.
On Monday morning, I went swimming with my aunt and uncle, as per my usual routine. Trying to fit plastic shoe covers over kitten heels was not the easiest feat, nor was trying to slip back into skin-colored tights when my legs were still damp. I couldn't bear to wear my tights or underskirt after going in the pool, but I put them back on after showering at home. Needless to say, I got a few funny looks in the changing room.
It got pretty chilly in the afternoon, so I had to pop some leggings and a cardigan on while I worked from home. I enjoyed how feminine and polished I looked in this outfit. However, the underskirt was a bit of a nightmare to contend with when sitting at a desk.
Day 2: Tuesday
On Tuesday I rocked a vintage ensemble that my aunt gifted me. She estimated that it was from the '50s and I thought the flouncy skirt and matching jacket certainly echoed the era. I imagined this outfit would be worn by a 1950s teenager to a special occasion, such as a wedding or a prom. It was quite comfortable, despite its formal appearance.
I travelled to my singing partner's house and we had a rehearsal. It seemed rather fitting to wear this outfit when practicing routines for our '50s-inspired band. My friend admired the look, although I did feel a little too formal. When I arrived back home to begin work, I felt this outfit was much easier to work in than the one from the day before, as it didn't include an underskirt. I even think this would be a great ensemble for a contemporary party or special event, but I'd probably ditch the jacket because it's a little too demure for my tastes.
Day 3: Wednesday
On Wednesday I wasn't feeling so peachy. I had planned to go out shopping in the morning before work, but was feeling under the weather. So I decided to wear something a little more comfortable. I picked a '50s style pleated midi skirt and paired it with a thin sweater that featured a roller skate pattern.
I thought this would be something a 1950s teenage gal might wear to a local diner with her friends, or maybe she'd sport this look on a date to the movies. The top was a dream to wear after the slightly rigid dresses of days past. However, the skirt was quite heavy and got in the way when I was working from my desk. That being said, I just loved this outfit and caught myself wishing these kinds of styles were still sported regularly today.
Day 4: Thursday
Thursday came along and I decided to channel Sandy from Grease. I just couldn't resist the temptation any longer. I'd recently seen clips of the wonderful actors from Grease Live! and my passion for the fashion in this movie was reignited.
I rocked a mint green dress, paired with a powder pink cardigan, a pink gingham hair bow, and an ice cream necklace. I thought this outfit would be perfectly suited for an outing to a '50s ice cream parlor, and wished there was one around.
I was working from home most of the day, and I felt surprisingly comfortable and productive in my ensemble. I'd been a little worried about the heaviness of the necklace — since it's made of metal — but I quickly got used to it. This outfit made me re-think my usual work attire, which is comprised of tracksuit bottoms, any old tee that's lying around on my bedroom floor, and a hoodie. I felt way more professional and even more motivated than usual in this get-up.
Day 5: Friday
It was almost the weekend, so I decided to wear a garment that I love: my sailor style playsuit. I paired the romper with some sneakers that feature ribbon laces, the aforementioned bow hair clip, and some skin-colored dance tights. I also needed to wear a coat due to the chilly spring weather, so I sported my fanciest bright red one.
I went into my hometown for a dose of shopping, where I saw a friend who said I looked lovely, and then I came home to complete some work. I felt really free in this playsuit after days of wearing dresses and full skirts, and enjoyed the overall youthful and playful vibe of the look.
Day 6: Saturday
On Saturday I wanted to try something a little different, so I went for a rockabilly-inspired outfit comprised of biker-style jeggings, a tied checked shirt, and a red cardigan. I wore my hair in a high ponytail with a bow and sported short Wellington boots. Unfortunately, I couldn't wear shoes that were more fitting for the era because I went on a long beach walk with my dad that involved clambering over chalk rocks and exploring rock pools. I was also forced to put on my big ski jacket, due to the changing weather.
However, when we reached a pub to quench our thirsts, I took my jacket off while we had a drink. Amid the sensibly-dressed walkers and the dogs, I felt a little silly in my top. I buttoned up my cardigan in an attempt to look more like a responsible adult.
Day 7: Sunday
On Easter Sunday, my fiancé and I were going to his parent's house, where the majority of his family would be gathered for a buffet lunch. I decided to go for a '50s style party dress that I really love, but hardly wear because it's often too formal for day-to-day life.
I combined my cocktail glass print dress with a pink cardigan, an underskirt, my hair bow, some skin-colored tights, and my sneakers. I'd never worn this dress with an underskirt, but I totally loved it and thought it added to the overall feminine vibe of the piece. I wasn't sure what everyone else would be wearing, so I opted not to wear heels. In the end, I was pleased with my choice of outfit since everyone had made an effort to wear smart casual attire.
I also came to realize that I really love pink. It's such a fun and optimistic shade. I really enjoyed wearing this outfit, but I also loved taking off my slightly restrictive tights and underskirt when I got home.
What Did I Learn Coming Out Of '50s Dreamland?
As someone who adores vintage fashion, I absolutely loved dressing up like a 1950s teenager for a week. There were some downsides — like feeling restricted in petticoats, hosiery, and stiff dresses — but the positives far outweighed the negatives.
Ultimately, I enjoyed how these clothes made me feel most of all: youthful, fun, vivacious, and motivated. I also felt more feminine and ready for anything. These clothes were fantastic to wear for work, as they usually tread the line between smart and casual. Even though I had no co-workers to show my personal style to, I felt way more professional, motivated, and inspired in vintage-style workwear. However, I'll probably ditch the petticoats in future because it really is difficult to fit them under a desk.
This experiment has inspired me to wear more fun, vintage styles on an everyday basis, rather than saving these garments to perform in or for special occasions (aka never).These styles made me feel full of energy and life. Considering all of the responsibilities that usually come with adulthood, it can be difficult to remember that you're only as old as you feel. But '50s teen fashion helped me feel less encumbered by being a grown-up and more optimistic about life's possibilities. I would recommend that anyone try dressing like a 1950s teen. Even if only so you can sing "Look At Me, I'm Sandra Dee" and mean it. Those Pink Ladies sure knew how to have fun, after all.
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Images: Phoebe Waller
