Reclaiming Dresses as Comfy Casual

Making the case for dresses as the ultimate comfort clothing

I don’t know why but for some reason putting on a dress always feels a bit like dressing ‘up’. Be it a mini, a midi or a maxi dress, it always feels like ‘making an effort’. Like I should only be doing it when people will see me. Which is kind of weird, because dresses, when you think about it, are the ultimate easy outfit. You only have to choose one piece of clothing, and you’re done. Sure, sometimes you have to think about what you wear underneath, but for the most part you can just throw it on and go. With many of us working from home and stuck indoors, it’s easy to reach for the comfiest and cosiest options, which we don’t usually think of as dresses. But why shouldn’t we? Dresses should be considered a go-to comfort option. They’re simple, easy, and flexible. With this in mind, I’ve ‘made an effort’, delved into my wardrobe, and chosen a week of comfy work from home dresses, in the hopes of persuading you to try your dresses next time you’re stuck for what to wear.

Before we get started, a pro-tip: If tights are one of the reasons you don’t consider dresses a comfort option, invest in some seamless ones. I used to detest wearing tights, but since I discovered seamless ones I actively enjoy wearing them. They’re like super cosy and soft leggings. Marks and Spencer in the UK do them, and you can find them online at places like Heist. They might be a bit more expensive thank your average pair, but in my experience they last a lot longer, so they’re still pretty good value.

Back to the outfits: here are some dresses I chose for sitting at my desk, lounging on the sofa, and getting out on my iso-walks. All dresses, and all the height of comfort.

Gingham Dress – Mango

Full length photo of neutral colour gingham dress, with a fabric belt tied at the waist and buttons down the front of the skirt.

Starting off with a favourite. The world seemed to go crazy for gingham last year, and I was totally there for it. I had to hold myself back from buying every iteration of a gingham midi dress I could find, in every single colour. Exercising considerable constraint, I went for this neutral one from Mango. I like the button detail and the wide, boat-neck cut. I’m never quite sure where to tie the belt – I’m tempted to try it at the back but worry that might look a little milk-maidy. It has a triangle opening at the back which did once make me question whether I had it on the right way round – you could probably get away with wearing it back to front! The opening gives a bit of maturity to what might otherwise be quite a girlish look. Massive bonus points for having pockets!

View of gingham dress from the back showing triangle wrap opening.
Yes, I did struggle to take this photo!

As an early aside, I currently have a grand total of two jumpers/sweaters (the rest are in my shipping), one of which is an enormously chunky, bright green one that doesn’t work with dresses. So if I do need to layer up it’ll almost certainly be some variant of the below: a light, black jumper knotted to give it some shape. I quite like the kind of ’50s silhouette this gives.

Full length photo of gingham dress with black jumper tied over it.

Floral slit midi-dress – New Look

Another relic of trends soon to pass, this New Look dress was kind of an early example of the prairie dress craze. The ditzy daisy print certainly suits that theme. But the cut itself reminds me more of 1930s evening dresses, with the little raised shoulders and the high neckline. There’s a key-hole cut-out that goes about halfway down the back, and a slit at the side, which stops it feeling too ‘modest’. The slit is a bit higher than I’d usually go for, but it’s so far to the side that it doesn’t present much risk. I love the sleeve length on this dress, it seems to hit at just the right point.

Full length photo of black daisy print midi dress with sleeves half-way down the upper arm and a high neckline.
Doing my best Angelina Jolie impression to show you the slit!

Given the hyper-femininity of the dress itself I like to pair it with sneakers for a slightly more casual and masculine edge. These are a recent purchase from Cotton On (my first in Australia!), as I realised I had basically only brought sandals with me. The white with black details is easy to match with a lot of outfits, and I like how it leans into the monochromatic look of this dress.

Blue open-back dress – Warehouse

Full length photo of rich blue sleeveless A-line dress.

This dress has been in my closet for longer than any of my other selections, and it has certainly earned its place. It has enough interest, with things like the waist detail and the back opening that you can get away without many accessories. I think simple is better when you’re working with such bold colours. I adore this rich blue, and love the way it brings out the red in my hair. Once again this dress has pockets, and they’re actually deep enough to hold my purse, phone and keys! Such freedom! Strictly it’s not open back, it just has a sort of flap/panel/vent (you can see it sticking out at the sides), which is greatly appreciated on a hot summer day. Despite being quite a wide A-line, the skirt is long enough to not blow up in the wind on a breezey day, so it is maybe my ultimate comfy dress!

Little black dress – Nasty Gal

Black dress with short sleeves and small buttons down the front.

There had to be a little black dress in the list. This one is maybe a little bit low-cut for work, but I think you can get away with it for work-from-home. Otherwise you could pop a camisole under it. It’s got a lovely streamlined, sort of skater dress shape, which just drops right over me, and the material is really soft. There’s just a tiny bit of detail with the buttons, which you could pick out with a brown belt and accessories. The dress actually came with a fabric belt, but as is so often the case with me, the loops for this sit some way north of my true waist, so it doesn’t quite work. Sadly no pockets on this dress, but overall a super comfy option. I think the slightly younger shape of the dress suits sneakers, or maybe Birkenstocks.

Polka Dot Dress – Warehouse

Full-lenth photo of mid-lenth dress with pink, peach and white polka dots.

No survey of my wardrobe would be complete without a bit of polka dot. I only recently realised how much of it I own. Perhaps years of owning dalmatians has rubbed off on me! Another Warehouse find, I love the floaty fabric of this dress, and the sort of ’40s tea-dress shape. The polka dots are in several colours (one of which happens to be my perfect lipstick shade) and have slightly rough edges, so it doesn’t feel too dominant a pattern. I think something might have gone a bit wrong with the collar on this one, as I can never seem to get it to sit right. At work I wear a cami underneath, as there’s only one button holding the front shut, so it can gape a little. However, it’s such a cheerful and easy dress that I usually find myself reaching for it on those days when I’ve overslept and can’t be bothered to put much thought into what I’m wearing. In the spirit of comfort I’ve paired it with sneakers, but for actual work I’d usually wear it with a pair of black block heel sandals.

And finally, a close-up where you can see that collar detail a bit better, and my actual face! Lockdown grow-out and all! I cut my hair short in December and it is quite desperately in need of a cut.

Upper-body photo of Helen in polka dot dress with folded collar.

Apologies for the mirror shots in this post; my tripod is in my shipping container, so it will probably be some weeks before we are reunited! I’ve enjoyed taking a look through my wardrobe and realising just how much I appreciate a comfy dress. They are more versatile than you’d think, and give a kind of freedom that even the baggiest jeans couldn’t match. I hope you’ll be inspired to dig out some old favourites from your own closets.


What have you been wearing to get you through the last few months of strangeness? Are you working from home, and if so, what have been your go-to outfits? And do you agree that dresses can be a great comfort option, or do you remain unconvinced? Let me know in the comments!

3 comments

  1. A nice, comfortable-looking collection you have. 🙂 Here in northern Massachusetts it’s been mostly too cool to wear dresses yet, so I’m rotating through my comfy pants, turtlenecks / hoodies and sweaters. I did make myself a sleeveless linen dress a summer or two ago, and have been meaning to sew a few more for everyday home lounging. (With pockets!) So, thanks for the reminder; I’ll have to pull out my stash to see what I might get inspired by.

    Liked by 1 person

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