How to look stylish when naturally you’re not!

[Bennettfan]

If you’re not somebody who finds it easy to look put together, but have found techniques/approaches that help - what are your top tips? I’ve always loved fashion, admired clothes. Feel much better when I feel I look smart. But have always struggled, hair not quite right somehow, clothes not quite right, feel a bit scruffy. Every month I buy a few new clothes and when I hit ‘pay’ I sort of think that finally my wardrobe will work. But it never does and the next month I’m buying more things trying to find the elusive solution to looking stylish/elegant/put together. Any tips?

From looking at people out and about, one thing stands out - do wear clothes that fit well. So many women of all ages are bulging out of clothes - often stretchy - which are too small, and it always looks terrible. Also in summer too much unattractive bare flesh on display, and too much of the garish tropical print stuff that shops sell at this time. Maybe OK on a beach abroad but otherwise no. I can't believe people don't look in a mirror before going out. Ditto wearing something that's a 'trend' regardless of whether it suits your size, shape and age. No, I'm no fashion plate but I do make some effort to look reasonably put together before stepping outside.

I have Stylebook which I’ve used for years. I left briefly and went to Whering and then came back when the new version came out.

Loads of food for thought here! So glad others are enjoying the thread 😀
I desperately need to buy a new swimsuit (have had the same one since I was 25 and am now early 40s) for a holiday this summer. It’s funny writing that down - I’ve bought countless t shirts over the last 15 years - but not another swimsuit?! How has this happened?!
anyway apart from a swimsuit and maybe a bikini, I’m not going to buy anything for a few months and see how I survive. I think just having a break from online scrolling of shops will be good. Also maybe make a resolution to actually go to the shops properly. I used to love going to look at shops - I think actually trying things on in a changing room rather than endless ordering and keeping it because it’s ‘alright’ is a good idea.

Part of the problem though is that many stores do not have physical stores or have only one or two. If you want clothes from certain brands then you do have to order online.

Perhaps you just need to re-focus your scrolling, @Bennettfan? I can’t really imagine getting dressed purely from my local high street / shopping centre, it would be impossibly restrictive.

Anyway - swimming costumes …

https://www.theguardian.com/thefilter/2025/jun/26/best-womens-swimwear-uk

https://www.vogue.co.uk/fashion/article/best-swimsuit-brands

Thanks for the recommendation! I bought the Kindle version yesterday and am finding it really helpful. The approach she recommends seems so logical that I'm wondering how I got to age 53 without working it out!

I'm not a clothes hoarder and have no qualms about getting rid of stuff I don't wear, but I guess unless you address the faulty thinking that makes you shop unwisely in the first place, you're going to carry on making the same mistakes!

This is total bollocks.

Glad you're enjoying it. I revisit it a couple of times a year; I've got my book out now to compare what I wanted to where I am. I've realised some of what I pie on my mood board is looking a bit dated. Time for a refresh!

It isn't. A bra that fits is vital for many of us.
The others are suggestions and most are valid.

Bet you’re lovely! Maybe save some of your clothes money and travel more? I had my colours done ages ago and I am a paintbox spring. I wear the bright clear greens blues and red yellow dresses / t shirts/ jumpers with neutral bottoms shoes, bag jackets all year round. Natural fibres and a good fit. Some things are 20 years old and get compliments. Ebay when I fancy something particular and a monthly trip to a good local charity shop. Pintrest for capsule wardrobe ideas. Regular hair trims, clean shoes, good coats, simple good skincare and makeup and a smile. I can’t be bothered with clothes shopping unless I am on a mission.

Be thin and don’t wear a top and a cardigan together? Bollocks.

Be fair. She might have meant don't wear a top and skirt together. I often go completely skirtless and get loads of comments.

Sorry, @dramallamabananababa - very new shopping relationship, and was waiting for my first delivery!

https://www.tracksmith.com/

They have bewitched me with sheer romance … So much so that rather than waiting until I’m next in London I ordered a pair of shorts from their clearance section, just to be able to have them in my grasp (and to check sizing before buying anything full price). They’re gorgeous, with all sorts of hidden delights. (Do running shorts usually come with internal underpinnings? Not sure I’ve bought any since Freshers’ Week circa 1983 - and even then I was so distracted by all the options I missed the introductory meet-up. That was the end of my rowing career.)

Buy dresses and skirts that are lined or always wear an underskirt. Clingy clothes are unflattering.

I recently put on weight due to needing steroids and i hated looking in the mirror, none of my clothes looked or felt nice and my hair no longer suits my 'moon' face. When i was told id be on them indefinately i cried because i dont look like me anymore. So i decided to stop working against myself, i wear mostly swishy dresses in bright colours, bright but comfy sandals and matching bags. ive had a sraight dark bob with fringe for most of my life, that i love but my hair is getting wavier as im getting older so im embracing curly hair for the first time ever. I actually feel more put together and stylish then i did before the steroids, i guess ive found my look.

Forgot to say op that initially i separated my wardrobe into two sections. The few new clothes that i loved on one side and a few older but key items on the other side to fill gaps as i replaced them with more clothes that i love. If it doesnt make my heart sing then its not going in my wardrobe or my body. It may take time to build it up but in the end you ll have a wardrobe of clothes you love and feel confident in. Oh and accessories are a great way to cheer up older clothes until you can replace them.

Thin isn't a good look, but slim is.
I don't think shoes need to be leather, but they generally look better than fake leather, suede, canvas, rubber etc
Cardigans don't usually look stylish.
One colour (+neutral) usually looks more stylish than prints

The 'total bollocks' was uncalled for.

place marking

I stand by it.

I’m currently on a city break and the most stylish person I’ve seen was a young girl, probably size 18, wearing polka dot trousers, a bright red blouse and Converse. Style is about attitude, not size or rules.

I agree with @RemusLupinsBiggestGroupie.
The Sezanne button fronted cardigan has been one of their highest sellers. I lived in my Cashmere cardis last year. All these sweeping arbitrary rules are just silly. You're saying that short people will never look smart?

At the risk of sounding a dreadful pedant, are we talking about being stylish or well dressed? I don't think of them as the same thing.

I think anyone can be well dressed by following some rules. (Yes, we might disagree on what the rules are but I'm parking that one for now.) But stylish, for me, involves some independence, creativity and risk.

So take the current Princess of Wales and Princess Diana: both tall and thin (Diana an inch taller, I believe) and money no object to either of them. I can't remember ever seeing Kate put a foot wrong but she plays it safe and to me never looks like she enjoys her clothes that much (and there's no reason why she should - lots of people feel like that). Princess Diana, on the other hand, clearly loved clothes and wasn't afraid to push the boundaries and go her own way. When she got it right, she looked amazing but sometimes she made mistakes and looked a bit of a fright.

I'd say Kate is extremely well dressed and that Diana was stylish.

Nothing wrong with either but I think they're two different discussions.

Yes, yes and thrice yes.

I completely agree. I don't understand some of the such (mercifully quite few) formulaic responses. For me, stylish is more of an attitude, and somehow for many people, simply that the things they wear just suit them or their personality so well. They can look elegant, or interesting, or quirky or even a bit scruffy, and just look so nice/appealing. It's hard to put a finger on it. A PP on page one said that if you wear things you absolutely love, and feel comfortable in, and that are true to your style, you'll probably look great, and I agree. Tall/thin doesn't come into it for me, for example.

I love it when people wear a more grown-up version of their old style of their youth. For example, I love spotting the grown-up goth when out and about! I've only just rediscovered my style after having children. I was very slender/willowy before having babies. Afterwards, with some weight gain, I wasn't used to my new body and just wore things that covered and hid it. I've since discovered that I look miles better if I don't try to hide, and so I'm back to the alternative/bohemian style of my younger days, only a bit more appropriate to my current lifestyle. Heaven knows if I'm stylish, but I feel great and much more 'me', and get compliments.

The thing is, being slim shouldn't be the be-all and end-all for looking good, but it's hard to claim it's total bollocks when the vast majority of women want exactly that. And mostly because of looks, not health. When we say clothes are 'flattering', we mostly mean they make us look slimmer. I wonder what proportion of women don't think they'd look better in their clothes if they were a bit (or a lot) slimmer.