A Week of Vintage Inspired Outfits

Creating vintage-inspired outfits with clothes I already own

I’ve recently fallen down a bit of a vintage clothing Youtuber rabbit-hole, starting with the wonderful Rachel Maksy. I’ve always been drawn to the classic chic of the New Look, and the cosy, knitwear-heavy styles of the 1930s. I think the clothes of these periods just suit my body-shape – few people can have been more relieved than me when low-rise jeans went out of fashion (and long may they stay out!). However, far be it from me to rule out older decades as a source of inspiration, even far older ones. Inspired by this burgeoning interest, I thought I would challenge myself to a week of vintage inspired outfits!

I don’t actually own that many vintage items, so part of the fun of this challenge was recreating vintage and historical shapes and silhouettes with modern items. I am pleased that quite a few items I wore this week were rediscovered through Shopping my Shipping, or were things I don’t wear very often. It’s always satisfying to give clothes a new lease of life. So let’s take a look at the pieces I put together for a week of vintage inspired outfits!

Monday – 1940s Student/Dark Academia

Full length photo of Helen in a khaki mid-length skirt with buttons down the front, and a burgundy cardigan over a white and floral print shirt, with brown brogues.

Starting the week off with something cosy and comfortable, I paired this burgundy cardigan with a long skirt, and popped a patterned shirt underneath. All three of these are things I don’t wear very often, and I think I’ve only worn the skirt a handful of times. It isn’t quite true to period as it has an asymmetrical hem, but you can’t really tell, and I think it has enough volume to suit a 1940/1950s look. This was inspired by academic outfits of the 40s and 50s, something I leaned into by pairing it with my tortoiseshell, round-framed glasses. It’s not quite what you’d call Dark Academia, but I think the autumnal palette broadly fits that theme. It would have been perfect with my black Oxford gown (which looks like a cape), but sadly that stayed home in Blighty. This was a really cosy, warm and comfortable look, and made a good start to the working week.

Head and shoulder shot of Helen wearing a burgundy cardigan with a white and floral print shirt underneath, and tortoiseshell colour round framed glasses.

Tuesday – 1890s Country School Ma’am/Cottagecore

Full length photo of Helen wearing a light yellow/green and cream gingham dress over a white shirt with the sleeves rolled up, with brown brogues.

Shooting back a few decades but sticking with the academic theme, this outfit made me feel like I was a character in an unusually cheerful Thomas Hardy novel. Like I might wake up with the sun to milk my cow before walking into the village to teach a class of local lads and country girls. Some serious Cottagecore vibes. Basically, I love this outfit and it made me feel great. This is a summer dress I struggle to wear in the cooler months, but with this shirt tucked underneath (which as it happens is the one I wore for my university exams) it works well as a seasonal transition piece. Maybe it was just because it was lovely and sunny that day, but I think this was my favourite outfit of the week. It fits me really well, the waist is in just the right place, and it makes me feel like a literary heroine. What’s not to love?

Wednesday – 40s Knitwear

Full length photo of Helen wearing a green and thin white striped dress with a cream jumper over the top, with a brown belt at the waist and brown brogues.

Tuesday’s sun had disappeared and Melbourne was plunged back into the cold, so I thought it was a good time to try out this 40s layering option. Credit to Rachel Maksy for bringing this look to my attention – it’s one I was aware of but didn’t think I had the items to pull off. Rediscovering this cream knit (actually just from Zara, but it does look quite vintage) enabled me to give it a go, and I think it works quite well. The shorter sleeves of the jumper make it a bit tricky as a top layer, but combined with the little slits at the side make it really suit this style. It’s certainly more casual than other iterations of this style I have seen, and I have since found a more appropriate belt, but again, it was cosy and comfortable. The green and white striped skirt is actually another summer dress, which has a really deep V-neckline, making it hard for me to wear even on warmer days. So I was pleased to find a new way of wearing it. This style was a great discovery for me, and is one I’ll be trying with other skirt and jumper combinations.

Thursday – 50s Summer Skirts

Full length photo of Helen wearing a cream half-sleeved shirt with a blue and white gingham knee length circle skirt.

The second bit of gingham in a single week! Regular readers might recall that I have a bit of a thing for gingham. This skirt is another item from Zara, but it’s a full circle skirt, so has a really vintage feel. The waist is elasticated, which makes it slightly hard to style, but I paired it with this similarly light and unstructured shirt, with cuffed short sleeves and pointy lapels. When the sun went in (as it often seems to do in Melbourne!) I threw that same jumper from earlier over the top. All in all a cute look that allowed me to indulge in my gingham obsession, and make use of some neglected items of clothing.

Full length photo of Helen wearing a cream half-length sleeved jumper over a cream shirt, with a blue and white gingham midi length circle skirt

Friday – 1950s Formal/Austrian Folk Singer

Full length photo of Helen wearing a dark green silky skirt with a cropped black cardigan, black tights and black Mary-Jane heels.

This look really make me feel like a member of the Von Trappe Family Singers, so I thought I’d include a little re-enactment for you. Otherwise this was a pretty straightforward 50s inspired smart casual look, which I actually used to wear all the time in the heady days of going to the office. This is yet another Zara skirt, and one of my all-time favourites. The fabric is really soft and silky, and the way it folds and gathers makes me feel like I’ve in a Northern Renaissance painting (think Rogier van der Weyden’s The Magdalen Reading). This is such a classic outfit it’s hard not to feel good in it, and I certainly did!

Full length photo of Helen wearing a dark green silky skirt with a cropped black cardigan, black tights and black Mary-Jane heels, stood with hands clasped in front of her and mouth open as if singing.

Bonus – Saturday – Retro jeans

Full length photo of Helen wearing rolled up blue jeans with a white button-up polo shirt, a black belt, and black pointed open shoes.

I don’t usually include the weekends in these challenges, because I mostly wear very casual or workout clothes during these lockdown times. But this was an exception. Still pretty casual, but for a sunny and quite springlike day I thought I’d make a bit of an effort. These are my go-to high-waisted jeans, paired with a slightly cropped polo shirt. The top is too short to tuck into things, and I’ve really struggled to style it in the past. But popped over jeans and paired with these pointy heels I thought it had a pleasantly off-duty, late-50s/early 60s feel to it. Sometimes it’s nice to dress up at the weekends – even if you’re not going anywhere!


So that’s my week of vintage outfits! Honestly I found it easier than I expected, and it’s definitely something I’ll be trying again. I was pleasantly surprised by how many of my clothes lend themselves to vintage styling, and how comfortable I feel in them. It’s easy to associate clothing of the past with stiffness and discomfort, but the way the shapes and styles fit my body means that couldn’t be further from the truth in my case. I’ll certainly be making a point to draw historical inspiration for my future outfits, and who knows, maybe I’ll even venture a little further back in time?


How do you incorporate vintage pieces and styles into your everyday wardrobe? I’d love to hear your hints and tips, so please do leave them in the comments! Thank you for reading!

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