Trying to look stylish when you just want to wear super comfy clothing - what to wear

[RJB73]

I follow a lot of fashion influencers on IG and YT.

I love their look of smart trousers/jeans, beautiful tops and long line jackets/coats, even their causal wear is so smart and elegant.

However, that look is just not going to fit with my current lifestyle. I am 51 and in perimenopause and alongside my other health issues (IBS and endometriosis) I often feeling bloated and uncomfortable around the middle, I hate anything tight in that area. I am finding myself continuously wanting to wear sweatshirts, leggings and trainers. All very practical and comfortable for my health issues and my job in adult social care but not at all smart.

I just can't find a pair of jeans or smart trousers which feels comfy around my tummy and at 51 I am not quite ready for an elasticated waist just yet so I end up wearing my comfy high waisted black leggings all the time but I want to smarten myself up. I am 5'6 and a size 10 with slim arms and legs (bigger middle because of the endo/IBS/peri combo so I like to keep that area under baggier clothing). I don't wear dresses or skirts either as they make me feel frumpy even though they often look great on other women (saw a woman in M&S yesterday in a lovely long sleeved denim dress, thick tights and ankle boots)

How can I smarten up the sweatshirt/jumper and leggings look? Is it possible to wear these type of clothes and look smart?

This is the kind of look I love.

I’ve worn hush joggers to my office job. They’re smart enough if dressed the right way. I hate anything tight around my waist too but at 56 I’ve embraced the elastic waist, particularly a flat yoga waistband.

Ninepine do smart trousers that are made of athletic material so look smart. I love comfy but I like to feel “dressed” as well.

Do you follow Melissa Murrell & Invest in style on Instagram? They post loads of outfits like the ones you enjoy wearing & are great for inspiration.
You're very slim & can probably wear anything.

And surely if you like the smart coat & boots look all you need to do is to buy a smart coat & boots & wear with your leggings?
Or am I missing the perfectly obvious?

Swap trainers for boots.
Thick tall socks.
Leggings
Sweater
Nice coat
Nice scarf
Little bag

Sounds perfect to me, I'm sure you'd look fabulous being slim and such.

Hello, I hear you.
I love that look too but it isn't as comfy as leggings and sweater.
I'm currently wearing Lulu lemon yoga pants in navy (they do other beautiful colours), and a long line sweaty Betty hoodie (again navy which I love but have other colours too).
I think having these items in beautiful fabrics, in a great cut, in colours you love can make them look a lot smarter.
I wear smarter clothes as needed, although after spending yesterday suited and booted as an invited guest speaker I couldn't wait to change when I got home.
Good luck

You can absolutely get that look and be comfy.

I’d swap out jeans for a flowy midi or maxi dress or wool skirt, though. Much more comfortable and forgiving around the tum if you get the right garment…and still works with the boots, long coat, scarf look.

Jeans aren’t comfortable unless they’re that unicorn pair that fits like a glove and wears well (haven’t had a pair like that since the 90s!).

Trousers and boots are a faff to make work.

Loads of elasticated waist trousers are designed to be well cut and look smarter now. Ninepine as pp said, Saint&Sophia, M&S, Halara are all good options with a range of budgets. It used to be that only the middle aged wore elasticated waistbands and they were sneered at, but I think that era is over and they are no longer associated with 'giving up', whatever that might mean.

Just saw you don’t do dresses and skirts, sorry! Jeggings?

I'm new to the world of IBS, all fine until peri hit then suddenly my stomach started rebelling. Clothes are now a nightmare due to waistbands pressing on my often sore and always chunky stomach. I switched to a particular style of dresses for work that have no shaping at the waist, I have loads of them and switch between bare legs in the summer and thin tights in the winter. Nothing presses on my stomach and the dresses skim it so it doesn't look gigantic.

Outside of work, I've gone over to loose elastic waistbands, jeans, cargoes, joggers etc. I'm hoping it's not forever but I'm not prepared to be super sore all the time.

I recommend Saint and Sofia.

Elasticated trousers nowadays bear no relation to those available twenty years ago.

Here's some slightly different sweatshirt styles that I have & love. All different price points. I wear these with comfy barrel leg jeans or cords. They're not as tight as skinny jeans which I find uncomfortable. An alternative 'comfy' wear is an oversized Cashmere hoodie worn under a trench coat with leggings/jeans. I wore this the other day - M&S capuccino cashmere from ebay under a Primark Edit Khaki Trench .Lots of places do jeans with a flat front & some back stretch. These would be very easy to wear for you.

You can definitely pull off that style without restrictive clothing.

I have a friend who works in design and she only ever wears black leggings. It's a bit of a signature for her. She is super stylish. In winter she wears oversize cashmere knits and chunky boots/ trainers from obscure cool brands I've not heard of. In summer it's lighter trainers and beautiful silk, cotton or linen shirts. He go-to smart coat is a camel cashmere Max Mara she's has for years (which my teen DD covets), with a gorgeous slouchy Hermes bag she acquired from an oligarch who once took a fancy to her. Rolex watch. She has a razor sharp blonde bob, never wears noticeable make up and looks amazing and comfortable in her style. I guess the black leggings work as a bit of a canvas for the rest of her look.

you try could some flared leggings I brought mine in m&s they just feel a little more smarter.

Seasalt have their Crackington trousers which are pretty comfortable around the waist (I can easily look four months pregnant due to IBS). They button at the side so no zip and nice flat front, and you can undo a button when you expand and you can’t really tell. They have some elasticaction at the back.

Such trousers (and Seasalt) are not immediately the look you’re talking about - I also really like the pic you posted - but they can actually be styled in quite a modern, minimalist way.

Thanks all, I've made a note of all the suggestions.