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Looking good when it's not summer?!

23 replies

Isanyonereallyanonymous · 27/08/2025 09:46

I feel I have my summer wardrobe nailed - nice sandals, skirt and top or dress and off I go.
Hit the cooler weather and I have no idea. Spring/autumn tends to be jeans, t-shirt, cardigan, usually paired with Vans. Winter throw a hoody or knit top on. Shoes are often where I come unstuck. I have tons of pairs but not many day to day ones and never seem to know how to finish my outfit off with shoes.
I'm 36 and a size 12 (short legs, big bust, little waist but hips and a bit of a tummy)
How do I look good when floaty summer skirts aren't appropriate please?!

OP posts:
iidentifyasapapaya · 27/08/2025 09:48

Boots. You need a couple of pairs of boots

Isanyonereallyanonymous · 27/08/2025 09:51

Ooh. I do have 2 pairs of boots, 1 chunky heeled and 1 flat, both what I would call pirate style/slouchy, and a pair of biker boots. But that leaves me stuck in skinny jeans?

OP posts:
RemusLupinsBiggestGroupie · 27/08/2025 09:51

Definitely boots. I pretty much live in my DMs in winter. The soft leather ones don’t need any breaking in and go with lots of different outfits.

Comedycook · 27/08/2025 09:52

I'm the same op...hate winter dressing. I find it so much easier to look nice in the summer..much more simple, nice dress, pair of sandals. I hate feeling all bundled up... watching with interest

Comedycook · 27/08/2025 09:53

RemusLupinsBiggestGroupie · 27/08/2025 09:51

Definitely boots. I pretty much live in my DMs in winter. The soft leather ones don’t need any breaking in and go with lots of different outfits.

I like how boots look but do you not find it a massive pain to put them on and take them off...or is that just me?!

RemusLupinsBiggestGroupie · 27/08/2025 09:55

Comedycook · 27/08/2025 09:53

I like how boots look but do you not find it a massive pain to put them on and take them off...or is that just me?!

Generally fine - unless I’ve had a few drinks! 😂

Howthough · 27/08/2025 09:55

I actually find it easier to dress in cooler weather. My go to "uniform" is a dress or skirt/jumper, tights and boots.

Iloveshihtzus · 27/08/2025 09:57

What are you most comfortable in - trousers:jeans or skirts/dresses?

I agree you need good boots and trainers. I have thick soled Chelsea boots and a pair of thick soled Chelsea-look wellington boots, so I wear these on wet days, with my favourite jeans, a wool jumper - sweatshirts and hoodies never look ‘put together’ - and a really great raincoat. I spent a lot of time getting this look right as where I live, I spend 90% of winter in rain gear.

On a dry day, I wear the same outfit with trainers - a variety, I love trainers, lots of nice colours like green and orange- as my main outfit is usually navy.

If you prefer skirts/dresses, just pair with good boots - maybe like Grenson Nanette( a lower priced version!) and a coat that is longer or the same length as your skirt.

TheLeadbetterLife · 27/08/2025 10:02

I feel the same, I much prefer Summer dressing, and also hate being bundled up. I like the look of boots, but I feel too heavy in them, like I've got weights strapped to my feet. I feel slightly panicky if I can't get them on and off quickly, so I won't wear any with laces.

I tend to live in jeans or flannel bags in the Winter, with a shirt or jumper. I have a cashmere lounge set for the evenings, and nice socks. Ride it out until the Spring, when I can be barefoot and fancy free again.

EscapadeVelocity · 27/08/2025 10:02

Your skirts need to be more extravagant in winter. Fabulous fabrics, volume, extreme lengths (long or short) paired with as much layering as you can manage, great boots and a huge coat. Oh and a beanie or whatever hat suits you best. Plus eye catching gloves.

Winter is incredible fun to dress for!

RemusLupinsBiggestGroupie · 27/08/2025 10:24

EscapadeVelocity · 27/08/2025 10:02

Your skirts need to be more extravagant in winter. Fabulous fabrics, volume, extreme lengths (long or short) paired with as much layering as you can manage, great boots and a huge coat. Oh and a beanie or whatever hat suits you best. Plus eye catching gloves.

Winter is incredible fun to dress for!

It’s also perfectly possible to look good in winter without channeling one’s inner Helena Bonham Carter, of course.

Some people (me) would look like a deranged bag lady if I dressed as you describe, though I agree it can be good on some.

Comedycook · 27/08/2025 10:26

RemusLupinsBiggestGroupie · 27/08/2025 10:24

It’s also perfectly possible to look good in winter without channeling one’s inner Helena Bonham Carter, of course.

Some people (me) would look like a deranged bag lady if I dressed as you describe, though I agree it can be good on some.

😂i thought the same!

JustJazzy · 27/08/2025 10:27

I much prefer dressing for a/w!

If you like Vans how about a pair of the MTE Vans, I love mine in the a/w. I also have leather Converse and winter Converse that are waterproof and fleece lined. Boots, I love boots! I have Grenson Nanette, Dr Martens(various styles and colours/designs), Solovair(8 eye derby in oxblood, 11 eye astronaut in black and platform 8 eye derby in black with side zip), Indio mid calf cowboy boots, Rocket Dog and very old River Island ankle length western style boots
I mainly wear them with leggings, skinny or slim leg jeans, flared jeans, skirts/dresses with tights.
I don’t wear wide leg jeans/trousers too often in the a/w as it rains a lot here(I’m in Ireland).

CoubousAndTourmaIet · 27/08/2025 11:08

I'm the opposite, I struggle in summer. I love dressing for autumn/winter.

I wear a lot of denim or linen pinafore dresses over long sleeved t.shirts, thick cotton tights and/or leggings under the pinny if it's cold. Boots, always.

Cords are a good alternative to jeans and tend to be warmer. Cord skirts also look great, with chunky sweater and boots.

The key for winter is layering, but I suppose I'm another Helena Bonham Carter type.

EscapadeVelocity · 27/08/2025 11:16

Ho hum - another Style and Beauty thread where anything other than M&S leggings or jeans is condemned as deranged.

<Yet again wonders what on earth the point of this board can ever be …>

xSideshowAuntSallyXx · 27/08/2025 11:36

I wear lots of mini skirts,tights and boots in winter. Usually with a jumper, then a wool jacket or coat or leather biker jacket. Amd always a scarf.

If I'm just out and about it's usually jeans and trainers. If it's really cold then I wear boots but it has to be really cold (I am one of those people who bares her ankles all year round).

Depending on weather I'll wear a fedora, woolly hats just make my hair a mess.

I also invested in some thermal tops from M&S last year. Best thing ever!

TheLeadbetterLife · 27/08/2025 12:01

EscapadeVelocity · 27/08/2025 11:16

Ho hum - another Style and Beauty thread where anything other than M&S leggings or jeans is condemned as deranged.

<Yet again wonders what on earth the point of this board can ever be …>

Oh come on. The style you described is very cool, but for those of us who hate Winter clothes all that layering and heavy fabrics might as well be a strait jacket. If I had to dress like Mrs Lovett I'd probably literally start making people into pies.

And I never wear leggings.

evilharpy · 27/08/2025 14:48

I think I'll be looking back through Claudia Winkleman's stylist's instagram for inspiration. That and cropped wide leg jeans with my array of lace up boots. I agree OP I find it so much easier to dress in summer when it's not freezing and it's less likely that the bottoms of your wide leg jeans will soak up the rain.

RemusLupinsBiggestGroupie · 27/08/2025 14:56

EscapadeVelocity · 27/08/2025 11:16

Ho hum - another Style and Beauty thread where anything other than M&S leggings or jeans is condemned as deranged.

<Yet again wonders what on earth the point of this board can ever be …>

Except that didn’t happen.

TheOGCCL · 27/08/2025 21:22

I much prefer summer dressing (no dresses or floatiness for me though). I think it’s shoes for me too, sandals are so easy and tend to be quite flattering and leg elongating. Summer just seems so much more forgiving generally, the light is kinder and I wear brighter clothing and jewellery which makes me feel more glamorous. Layers aren’t really my friend as they bulk me up.

Trainers can get you through quite a bit of winter, I think metallic ones keep things lighter whilst still being warm. Boots yes (never black though) and I will sometimes turn up my trousers for a lighter look when wearing chunky boots. I like to wear thin cashmere or wool rather than bulky jumpers. Cord trousers as pp said. It’s trying to channel that summer insouciance and keeping warm at the same time.

I do still like the skinny jeans and knee high boots look.

Isanyonereallyanonymous · 29/08/2025 23:59

Thanks everyone. Lots of ideas to pick at!

OP posts:
Lollipopop · 30/08/2025 00:14

OP, we are opposites! I hate dressing for summer but love autumn and winter. I’m also 36. V tall, broad shoulders, size 10. I don’t really do swathes of fabric although I’d love to be able to pull off HBC’s style.

I mainly wear jeans. Levi ribcage or similar, slightly cropped, if it’s raining - with chunky boots. Maybe something wider in dry weather, with trainers or ballet flat type shoes. I’d wear either a boxy or a fitted ribbed plain tee with a cashmere knit. Or a white shirt or lacy blouse thing. Maybe a little silk scarf, or a woolly one when it’s really cold. Trench or wool coat, or hideous puffy caterpillar coat with a cashmere beanie for the school run.

henlake7 · 30/08/2025 10:31

I never understand how jeans are so popular in the winter. It gets too cold for them fairly early for me and then if they get wet they are horrible.
I swear by those fur lined leggings from Primark with a thermal vest/top as my base layer. Then I layer it with either a vintage style dress, pinafore dress and jumper (I have soooo many pinafore dresses!) or a skirt/trousers and jumper combo.
Then its chunky boots...the chunkier the better and a big chunky cardigan....the chunkier the better!😄
oh, and scarves, hats, gloves, dramatic coats, etc.

Obviously I am a winter clothes person and clearly we all seem to fall into 2 camps, judging by the comments!😅

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