How can I feel more comfortable wearing dresses and skirts for ‘everyday’?

[Askinvillarblues]

I am a sahm, spend most of my day either dog walking, riding or on the school run (obviously with all the home based crap like laundry, tidying, beds etc) with the odd coffee/lunch with friends thrown in. Most of the time I just chuck on a pair of jeans and a jumper which I’m comfortable in, BUT I keep buying dresses and pretty tops. I have this vision that I’ll wear my dresses etc day to day - they aren’t fancy sparkly ones, just cord pinafores/ floral dresses to wear with tights and flat boots/DMs, but I feel self conscious at the idea of ‘dressing up for the school run’ when the sad reality is that I don’t go to many other places that don’t involve mud and animal hair 🙄🙈. But I want to wear my nice things! How can I change my mindset so that dresses/skirts feel more normal? Or how can I hold myself back from the pretty things and focus on the practical things I would actually wear rather than the ones I imagine myself wearing?

Why is a skirt considered pretty?
And why do we think wearing a strip of fabric over our legs that doesn't have two separate sections (trousers/jeans) mean we are more dressed up?

It is all a matter of perception.

You may be the type who doesn't really feel comfy in them day to day. Ir you might be holding yourself back when you'd love to incorporate them into your everyday wardrobe. Only you can fathom with this is.

I was like this for years. I loathed jeans and trousers, but wore them to death. It felt 'normal' and casual. Because the market has prioritised them as easy, whereas dresses and skirts found themselves resigned to the party bin.

I don't get this, personally, and don't see the issue. It's great that women have so many options (unlike men and whatever), but we do tend to bog them down with associations that are meaningless really.

You absolutely can walk a dog in a dress. The important thing is the coat and footwear. One could as easily snag on a bramble in wide trousers as much as a thick, winter appropriate dress. The fact that it is open throughout the leg makes no difference with the weather.
The issue is, as I see it, the market primarily creates coats that work well with jeans. The ubiquitous denim. and as hardy as denim is (that is what it became famous for), im always baffled as to how such a stiff and peculiar garment took over our priorities.

Good boots, a long pair and some ankle/doc style boots for winter go with most dresses. If you want to explore this, choose wonder dresses with more muted, seasonal colours and a heavier weight (preferably with the skirt lined). I see many women in rural areas powering about or dog walking in skirts and dresses all the time. Coats are a different matter though, and especially raincoats. Everyone says you shouldn't wear a dress that is longer than your coat but this is also complete bollox.

I have seen some awesome, casually dressed woman in dresses, boots and shorter rain macs. Just try to avoid lurid or overtly crazy patterns. I would also recommend natural fabrics, which are rare and expensive, so there's that to think about too.

I had the same and making a concerted effort to actually wear them, even if it was just around the house, made the difference for me.

I forced myself to put on dresses that had been hanging in the wardrobe. Over a couple months, I got more comfortable wearing some of them 'just because' and realised I didn't like others as much as I thought and got rid.

I've read it can be a confidence thing not feeling like you're worth wearing nice clothes everyday. If that's what's holding you back, just wear them. You're worth it!

winter dresses, not wonder dresses, although id like to find one of those!

Brilliant question OP, and brilliant reply @pheasantlysurprised xx

... the only thing I would add is - find cardigans&boots that you feel normal in & that you'd normally wear with jeans, but that you can wear over/with dresses instead? So layer up, and dress-down your dresses!

Thank you so much for your replies. Some interesting points for me to ponder. I do wonder if it’s a confidence thing. I spent many years working in a office so am comfortable with more formal office wear, but can’t seem to get the right balance between properly dressed up and scruffs! I also think I’m worried about making an effort but getting it wrong in some way. No one would give two hoots what I wear round here so it’s definitely my perception rather than other people’s judgment (perfectly acceptable to rock up to the school gates in full on farming gear here!). I like the idea of forcing myself to wear them round the house so they become more familiar. I’ve got good boots (many, many pairs 😂) so I’m ok there, but maybe it’s the coats/jacket issue that is holding me back. Again I have many, but none that are just right!

@Pheasantlysurprised

winter dresses, not wonder dresses, although id like to find one of those!

Oh that's a disappointing clarification, I was looking forward to learning more about wonder dresses.

Just wear them @Askinvillarblues! I wear skirts and dresses all the time, town or country.

A parka goes well with a lot, and a bomber jacket too.

I love in winter dresses
Thick tights
Boots

It’s comfy warm and looks good

Highly recommend

Just don't do the washing. It's an effective way of getting to the back of your wardrobe

Once you've left the jeans at the bottom of the laundry basket for a few days, you'll soon be used to wearing other stuff. I find dresses and skirts need washing less often than jeans. The hems don't get muddy walking, they don't fit closely at the crotch. So it's eco friendly too!

I did it! Am wearing a navy cord mini dress with a cream polo neck jumper underneath- so still safely within my ‘jumper’ comfort zone 🙂. I do feel a bit silly dressed up as I’m literally going nowhere today (kids off school sick!) but my daughter said ‘you look pretty Mummy’ so I’ll take that 😁

I am in the same boat as homeworking is the new normal and I have fallen in to jeans and jumper mode for autumn.

Work on dressing down. If in doubt stuck a pair of black trainers with what you're wearing. Also make sure you are warm and comfortable. Some merino tights for the cold days, a decent selection of tops to go under dresses or stick a jumper or cardigan over.

@Askinvillarblues

I did it! Am wearing a navy cord mini dress with a cream polo neck jumper underneath- so still safely within my ‘jumper’ comfort zone 🙂. I do feel a bit silly dressed up as I’m literally going nowhere today (kids off school sick!) but my daughter said ‘you look pretty Mummy’ so I’ll take that 😁

That isn’t remotely dressed up

Just a nice day autumn outfit

Ha, it probably isn’t dressed up, just that I feel it is compared to my usual jeans! Silly to feel that really

The more you wear them the easier it gets. I only wear dresses now and don’t even own a pair of jeans.

Honestly that is not dressed up, it's just ordinary to many people (in a good way!).

Do keep checking your thoughts on this and ask why we associate something we see as traditionally feminine with 'impractical' and 'overly dressy' - I think it's interesting and tragic at the same time.
And I know 'feminine' is a loaded concept, so not to get too deep here, but I do get tired of how many impractical or frivolous connotations society has placed upon it.

Just enjoy and see how it goes op!

I do understand where you’re coming from … I feel like dresses and skirts are for “going out” or for occasions where I want to get dressed up like a birthday lunch. During lockdown I got so sick of being casually dressed I vowed to take more advantage of dressing for day to day life which I have I think. I find there are ways of dressing down skirts and dresses. I like a boyfriend cardigan over a midi dress or an oversized sweatshirt or sweater with a midi skirt. I also like midi skirts over leggings and trainers or DM shoes. Jackets in denim, camo or military style or leather also can be paired to create contrast ( a bit like trainers with a trouser suit). Some skirts and dresses are not that formal to begin with - jersey, T shirt , sweatshirt or knitted dresses can look quite casual before you add footwear… you just need to make them warm enough. If you’re on Instagram then Style in the Stix have an interesting account. They are more dressed up than me but are in a rural setting which makes an interesting change. They’re really good at contrasts… a bomber jacket with a kilt for example. Essentially you need to bite the bullet and have a go because it’s the only way to tackle it

Just a matter of getting used to it I think.

I find leggings and a shorter skirt are more practical and comfortable than tights and a longer skirt - and can be worn with wellies if necessary!

Cardi, denim jacket or soft blazer, with a scarf draped around would make it look casual.

My uniform is a jersey dress ( must have pockets!) with leggings and flats or baseball boots. Range of cardigans and scarves to match.

Loads of great ideas here, thanks. I tend to go for shorter skirts rather than midis as I’m really short and too much material drowns me, but thick tights/leggings are definitely the way forward. No one needs to see me flashing my arse. I think you’re right in that it’s just a matter of getting used to it. And I do like a nice snuggly scarf 🧣 so that might be a way of dressing down a bit too. And jumper dresses! How did I forget about those?! I had some lovely ones back in the day. Will have to have a bit of a Google and see what I can find!

If I was into minis I’d definitely wear them with a boyfriend cardigan over leggings with hi top trainers or chunky boots. I’ve got a “pleather” pencil skirt that I plan to dress down in a similar way. I’ve started to keep an eye out in charity shops for men’s sweaters and cardigans which have good slouch… I have a couple of cashmere ones to date.

I am exactly the same.

I think part of the reason for me is tights. I hate tights. I recently got some good ones (heist) and they make a big difference. BUT they need to be washed on delicates which I don’t do often, so I will need to buy lots of pairs if I want to wear skirts more often. BUT they are £25 a throw .

Anyway you see my problem!

Snag tights are good. And I wash them on normal, in a delicates bag.

My casual winter style is pretty much mini dresses (actually normal dresses - I’m very tall) with leggings, chunky socks and boots. Definitely not overdressed, and comfy for getting up and down from the floor with dc

Oooh, ok I should try Snag. When you say normal wash do you mean 40 degrees?

Yes, 40 degrees in the same wash as normal clothes, just in a bag to stop them getting tangled/stretched.

IME it's not so much the dress, as what you wear on your legs to compensate for the no-nonsence covering up of jeans, and then you might need diffferent shoes or to get used to the idea of how your legs look with tights/boots/trainers/leggings etc.
I found opaque tights and knee boots/lace up boots got me started.
It takes a while to get used to a different look.