One pinafore dress, five ways

The surprising versatility of an over-looked dress

My closet has gone on something of a journey this year. Thanks to Shopping My Shipping, I’ve rediscovered a whole host of pieces that once lurked at the back of my wardrobe, and found new ways to wear pieces I had once dismissed. One of the best finds has been a simple black pinafore dress. Hitting just below the knee and with an elasticated bodice, this is a super comfy dress. But it’s one I’d hardly ever worn before. Mysteriously, I thought it was a bit hard to wear – how often in England is it comfortable to go so completely sleeveless? But not a little thanks to my experiments with vintage-inspired clothing, this dress has found a new lease of life. So I thought I’d share some tips for different ways to wear this style of dress, which has become one of my wardrobe staples. It’s just a simple, cheap item from New Look, but it has gone from least- to most-worn, and will never again be overlooked in an assessment of my wardrobe.

Short-Sleeved florals

Full length photo of Helen wearing a black knee-length pinafore dress with a short puff-sleeved top with red flowers on a white background, and black Mary-Jane shoes.

Starting with a simple but elegant feel, this outfit pairs the dress with a red and white floral blouse from Topshop. This top doesn’t actually fit me very well on its own, it has weird string ties down the front that never seem to close properly, is super see-through, and is too big for me. At the best I have to wear it with a camisole, and even then it doesn’t look great. But as a delicately feminine accent to this pinafore, it works perfectly. All the issues are cast aside, and it sits really well. I think proportions and neckline are important to bear in mind when layering under a pinafore. The sleeves of this top sit at a good length to not look too fussy, and the neckline meets up with the contours of the dress. Paired with classic Mary-Janes this is an easy smart-casual outfit, which pleasingly makes the most of two garments that together are greater than the sum of their parts.

Black and white polka dots

Helen wearing the black pinafore dress with a long-sleeved collared shirt underneath, with small, creamy-white polka dots on a black background.

Going in the other direction for sleeves, with this gorgeous polka dot shirt. I love this top, it is really silky and fits well. It’s just a really easy piece to match things with, so it came as no surprise that it works well with this dress too. This outfit gives me vaguely French vibes, sort of like an office-job Amelie. With my beloved patent brogues, it has a touch of sophistication whilst being office appropriate and eminently comfortable. Absolutely onto a winner with this look, which I’m sure to repeat again and again.

Dark ditsy florals

Helen wearing the pinafore dress with long, puffy, see-through sleeves underneath in a black with white and yellow ditsy print.

I’m going for a slightly 60s/70s vibe with this look, which sees these gorgeous sheer puffy sleeves bring a bit of fun to a dark look. I adore the sleeves of this top, but it doesn’t actually doesn’t fit me at all. I bought it from an online thrift shop and it is more or less my size, but it’s turned out impossibly large on me. So this outfit was a way to save a piece that otherwise I’d have had to part with. It works perfectly under the pinafore, and I just love the slinky sheer sleeves, with their cute pattern. Wearing this put me in a good mood all day, and with my faux-suede boots made me feel pleasingly witchy. The sleeves are light enough that you could wear this outfit on a hot day, but it also works for cosying up with a big cup of coffee and a book on a grim autumn afternoon. Definitely one of my favourite looks on this list.

Blue linen shirt

Helen wearing the pinafore dress with a rich, dark blue linen shirt underneath with the sleeves rolled up to three-quarter length, and black faux-suede boots.

I know a lot of people say blue and black don’t match, so perhaps this is a slightly rebellious outfit. But I really love the feel of this linen shirt, and I think it gives this outfit a very vintage look. I can almost imagine Emma Thompson wearing it in the perfection that is her adaptation of Sense and Sensibility, or with proper victory curls for a 40s look. Alternatively it isn’t miles away from the kind of thing you see at Son de Flor. It has a lovely light feel to it, and the blue really brings out the red (well, maybe orange) of my hair. I’ve got a few flannel shirts that I’d swap this for in autumn/winter, but for breezy spring days, this long-sleeved linen strikes just the right balance between cosy and cool.

Vintage inspired black and white

Helen wearing the pinafore dress with a long-sleeved, sheer white pussy-bow blouse underneath, black tights, and black Mary-Jane heels.

Another black and white number, this time with a slightly more vintage feel. I’m not quite sure I can count this as Edwardian, or more 70s does Edwardian, but either way I love it. This top is the Luiza blouse from Collectif (currently on sale), and I can’t get over these sleeves. I think it’d work just as well without the bow, but for a little extra flamboyance, it’s nice to have it out. I’m always on the search for work-wear with a vintage feel, and I think this perfectly hits that brief. Timelessly elegant, if slightly risky if you’re eating soup.


That’s it for my trusty pinafore. Truthfully it was hard to limit this to five outfits, because I have lots of tops that work really well with it. Perhaps I’ll do a Part 2 at some point. I’m just so delighted to have rediscovered this dress, and found ways to wear it in almost any mood. It’s a surprisingly versatile piece, and one I now have to resist wearing on a daily basis!


Thank you so much for reading! What piece of clothing do you own that you can wear in lots of different ways? I love finding these sorts of pieces that can do double, triple, or even quadruple duty, so please do share your ideas in the comments below!

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