Easy ways to feel more confident about your style
Photo: Annie Johnston
Personal style is a work in progress. I know, I’ve been working on mine for years. Not exclusively, mind you. I do have other falafel to fry… Just as with a favourite recipe pulled out on a busy weekday evening, co-ordinating an outfit gets better with practise. The jacket and jeans (or cargo pants) combo is one of my default, feel-good outfits. These are all items I’ve owned for a while and this new confidence-boosting configuration came to me in a rush to get myself to the Fashion Revolution panel discussion, a couple of weeks ago. Experimenting with style is the way to add flair and personality, but feeling comfortable and confident matters. It pays to have a reliable uniform of not-so-basic-basics, items that you can call upon when pushed for time and want to grab-and-go. For me, the just-smart-enough combination of casual cargo pants and a classic blazer is a winning formula. My desk buddy prefers a long denim skirt and a fitted jumper. We both want an outfit that works with comfy shoes and trainers. Business at the top, creative co-working at the bottom.
Here are five easy ways to feel more confident about your style:
Know your style
I had a really lovely message from a reader recently, she had left work and found ‘the loss of identity, personally and professionally challenging.’ But thanks to the invaluable writing both on the main stage and in the comments box of That’s Not My Age, the one thing she has learned is that you have ‘to know what you want.’ Style is personal and understanding what suits you and what you feel good in is the sartorial daily double. Get it right for the win-win.
If it works, wear it again (and again)
Many women wear the same outfit, or a version of an outfit, for two or three consecutive days. This is not slovenly, it makes perfect style sense. When you’ve found a winning combination, reissue it with a minor tweak (and clean underwear) the next day. Like leftovers for lunch, an outfit is tastier when it’s had time to evolve. I’ll wear the same jeans and jacket several days on the trot, but I’ll roll the jeans up and swap trainers for loafers, trade a simple t-shirt for a silk blouse, tie my hair up and add a pair of statement earrings. Stick to what suits and then switch things up.
If it doesn’t feel right, forget it.
There’s absolutely no point buying an item of clothing, or having something lurking in the back of the wardrobe, if it doesn’t fit right or feel right. For me, fit is the most important thing. I can’t stand armpit or crotch-bothering clothes. No-one wants to be constantly fiddling around with ill-fitting garments, faffing is not chic. Not so long ago, I was down to the last bra in the drawer, an item well past its sell-by-date but needs must and all that. I reached lunchtime and had to go and buy a replacement, the old one went straight in the bin. Less faffing equals more time to pursue other more important matters.
Keep a note of winning combinations
Having a record of all your top-notch outfits is a time-saving device. Take a photo (often, I have a quick look at my outfits online as a reminder, I guess that’s one of the advantages of plastering images of yourself all over the internet…), Lucinda Chambers told me that she keeps a list in a notebook as a reminder, alternatively, take notes on your phone or hang items together (possibly on the same hanger) in the wardrobe.
And don’t forget to experiment
Every now and then the not-so-basic uniform needs freshening up – and this involves experimenting with new combinations of clothes, adding a new colour or silhouette to the armoire. Earlier this year, a pair of camel suede boots introduced me to a number of new outfit possibilities, in different colour combinations, and a burnt orange leopard print fleece came together with a pair of ancient white jeans and last year’s velvet mules. Back to the favourite recipe analogy, take the essentials and then whoop them up with a sprinkling of new ingredients.
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Discussion (60 Comments)
I’m 5′ 10″ but I did buy a larger size (these are a men’s style from Stan Ray) because I wanted a looser fit.
Jeanne Edwards says:
Am having a huge cull of my clothes as decided to concentrate on a much smaller selection. I have found jackets I haven’t worn in years so am giving them another shot by wearing them casually. Bought two Blazers this year and wear with jeans and, like you suggested, T shirt or silky shirt. I absolutely love scarves and have a huge selection,! I do like cargo pants but at 5 feet 1 inch they make me look very squat as do rolled up jeans. Look better in ankle skimming pants and jeans.
Once again, thank you for your tips.
Jeanne
Virginia stewart says:
Hi Jeanne
I totally agree with all your comments, I have a huge wardrobe of nothing that matches. So out it goes and I now love my really old blazers, white shirts and jeans. It’s time to re focus on what we have and how to re use them
maudie says:
Oh god, Alyson you are so bloody inspirational. Since your blog I have found more confidence in wearing clothes that suit ME and wearing the same things re-jigged around for days on end. This post is, in a nutshell, where I am at now. I no longer try to please anyone else (husband, kids, friends. random people in the street etc.) and wear what I want to. I am comfortable, more confident and function on far, far less items of clothing. So a Big Thank You!
Steele says:
Excellent advice! I’m going to start keeping a list of favorite styling combos immediately. So true about wearing same or similar outfits day after day. Now that I am retired, there’s no one who sees me every day so I can get away with that. I pretty much follow the blazer/jeans system that you do, switching out shirts and scarves. You’ve helped me simplify my life.
just bought an oversized kaftan that I fell in love with as soon as I put it on …. it would not be considered sexy but I felt sexy in it. And I’m pretty sure my husband won’t love it but I’m not sure I care! Love your blog xo
Angie says:
Big Hooray for the kaftan….soooooo comfortable and definitely feels sexy! That is more than half the battle . A floaty kaftan looks like you’ve made the effort to get dressed up or you can wear it around the house (on a quiet day). I always feel good wafting around in yards of gorgeous fabric!
Lisa says:
There are some good apps if you want to record your clothes and outfit combinations. I use Stylebook (I’m not on commission for mentioning it!). It’s great for checking what I already own before I buy something new.
SFord says:
That would be what I need! I bought a pair of forest green block heels the other day for an event. Put them in my wardrobe to find the almost exact pair (also in green) I bought last year from a different store. At least I know that my style is consistent!!!
Miss C says:
Love your blog and have both of your books too Alyson. Another vote for Stylebook from me, I find it very useful for planning what to wear each week. It will also calculate a price per wear for you, once you start filling in the calendar, which can be very enlightening. I am not on a commission from them either
Hi Lisa
What I do to record my outfits is, I put them on, and photograph them with my Ipad, create a file for my outfits
Then I can download the photo from the outfits clothes file when required
Anna K. says:
Great tips, as always! For me, quality is a confidence booster. I think it was Georgio Armani who said, ‘Luxury is a private pleasure’. Wearing silk, cashmere, alpaca or whatever, and knowing a garment is well-made and fits to perfection makes me walk taller. Simple, quality stuff plus a zingy accessory – usually a great scarf in my case, is my uniform now and I certainly feel more relaxed and un-selfconscious about my appearance than I did when I was young.
PS- Love,love, love your top in the pic!!
Lesley Somerville says:
I saw this pic on FB and remembered I have a VERY old (early 80s) Jaeger blazer stashed in my wardrobe. Also have khaki trousers as recommended by you, and a lovely M&S blouse in similar colours to yours, bought a couple of years ago. You have definitely influenced me, for the good, and I find myself dressing better, spending less, and looking, may I say, pretty darn good. So thank you and all the other contributors who sustain this growing community of women.
Jane says:
I love this advice Alyson and all the comments. Please keep commenting!!
I am a long denim skirt and fitted jumper person (day after day with clean underwear and long socks – can’t bear hosiery), but will try your blazer and cargo combination one day .. have been looking for a good pair of khaki trousers since I started reading your blog. And have so far failed. Am shorter than you Alyson (5,7) and getting thicker round the waist by the hour. I also don’t suit tapered legs – need some volume round the ankles and favour the high waist, wide leg trouser shape. Any ideas from your readers? Another great post thank you !I second the khaki trouser debate – I don’t like tapered trousers and find the very baggy ones unflattering. Would love a straight leg or slightly wide leg in a khaki linen to suit someone who is 5 foot 6!
Anita says:
I don’t know if Eileen Fisher or j Jill are available where you live. J jill is less expensive brand and have good sales. I live in the US
Maureen says:
I just bought a pair from the men’s section of mountain warehouse. Great relaxed fit and pockets. Love them. Taken the place of my Levi’s at the moment
Sarah says:
I don’t know anywhere better online for style advice and community for women my age/stage.
Maisie says:
All excellent advice, especially about wearing the same outfit ,with tweaks, I do this all the time. Trying to come up with original combinations every day makes my head hurt ! I thought I’d found some new ( long-sought-after) cargo pants in your outfit suggestions until I saw the prices.Ouch ! Some budget-friendly options please !
Oh mine are Stan Ray, proper workwear – or try army surplus stores. But I will have a look at what’s around and get back to you on this, Maisie.
Barbara says:
How about the Carhartt Cargo Pants? Good fit, cut for women and a very good Prince.
Hi, Maisie – I bought some great cotton chinos (men’s!) from Community Clothing and they are PERFECT. (I am a big around the middle UK12 and I got a 32″ waist for comfort and bagginess). Didn’t break the bank either.
Jodi Brown says:
I’ve been thinking that these look good Maudie, company with a great ethos too. In fact, all their stuff is probably my style.
Joyce Morris says:
I don’t own much jewellery, but the pieces I do have, not necessarily expensive items, I love and often find something whacky, on something plain, completely transforms the look.
And this look, Alyson, is probably my favourite to date. You look brilliant.Barbara Thompson says:
I have an app I use to record the looks I have worn. You just made me realize that I should be noting on the app the ones that really worked. Wasted opportunity, that you have now inspired me to jump on. Thanks so much!
‘I can’t stand armpit or crotch-bothering clothes.’
This is why I love your column.
No one else out there writes like you – and especially not about fashion.
Thank you Alison.Love your looks…you’ve encouraged me to find my own style again after ‘work clothes’.
I would also be interested in reasonably priced cargos please!Ana says:
I love this conbination of casual plus formal, it looks elegant and comfortable; and the colour combinaton is extremely original as well, you are a very creative person
Jane says:
Alyson. I have followed your journey of growing out your hair to grey – looks fab by the way, well worth the effort. I have followed your footsteps and my final bits of blond were cut out 2 weeks ago. I am now struggling with what colour clothes to wear? I have always been strawberry blond and told I was an Autumn in colouring but none of those colours seem to suit. Black and grey are only ones. My grey seems quite cool to me and am in danger of running back to the hairdresser to get it coloured!! How do you manage now with the grey hair and colour of your wardrobe? Any tips will be most gratefully received!!
Lu says:
Jane, since growing my grey out, I’ve found that the colours in my wardrobe have completely changed. Actually, everything about my wardrobe changed once I’d got the hang of the grey! But the having to rethink the colour of my clothes was a surprise: I used to rely on my (bottle) red hair for colour around my face, but now with light hair and pale skin, I am having to think about adding some vividness. I find that pale colours drain me, and am wearing much more blues and greens than I used to, probably because they work with blue eyes to wake up my face. My sister, whose hair is whiter, but who has more olive skin and dark eyes, is able to go lighter and brighter than me. In general I think that colours with depth work well with grey hair, and properly set it off, as well as allowing the grey to recede slightly and let the colours shine!
I’d be interested to know how many others have found that a wardrobe rethink was in order after going grey . It may be because I used to sometimes dress like a deranged toddler, but I found that I wanted my clothes to emphasise the deliberateness of my decision to go grey, and so I tried to focus on a more thoughtful wardrobe, accrued carefully over time.
I’m exactly the same Lu, and have donated a lot of stuff for this reason. I’ve found that defining my brows but toning down the mascara has worked a tad for my face, but would love any make up suggestions for deathly white Irish skins like mine. My bright chestnut (eventually dyed) hair used to brighten my complexion. Now unfortunately, my face looks almost as grey as my hair!
‘deranged toddler’ is too funny and relevant to me. I used to try and be so experimental that my kids wouldn’t go out of the door with me! Apparently my pattern experiments made me look ‘like I was wearing a bus seat’!. Polar opposite now and far less exhausting!
AppleEverAfter says:
Great article and love your outfit, especially the way the top pulls everything together. What do you call pieces like that? The PET-P (pulls everything together piece) is a bit clunky ….
Marilyn L says:
I’m at a stage in my life where I need to reinvent myself! 72, retired, widowed in 2017 and no longer need the ‘going out’ clothes as my life is so much more casual and daytime. The first thing, I think, is a change of hairstyle. I’m bored with my bob and feel like a change. I need to feel more confident in myself and my appearance. I love the honesty of your blog.
Emma says:
I’d love an article on underwear please Alyson. I struggle to find bras and pants that support properly but are a little more unusual!
In the meantime great work! Thank youMrs Tonia says:
I went for the first time to Bravissimo for a sports bra with back fastening. Found just what I was looking for by Shock Absorber. Very helpful good service in the shop. Nice changing room with a little dressing gown to wear while waiting for the serving assistant to bring other designs to try on. I would certainly return there for regular bras too.
Goddessinthedetails says:
Is your desk buddy too shy to step up and be photographed? Her style sounds like mine. At the moment I just want maxi skirts (easiness of bare legs beneath) and T-shirts. For evening, a silk/silk georgette maxi skirt and a cashmere jumper.
Oh she has been featured once before but maybe it’s time for another appearance….
https://thatsnotmyage.com/beauty-at-any-age/when-its-time-to-find-a-grownup-not-groundbreaking-haircuts/
Esther Devaney says:
So enjoyed reading post and comments. I’ve taken on board all advise except not sure about repeating outfits over a few days but am hearing it simplifies life ! Certainly when travelling I re wear cloths …
when to go grey and how to look at colour changes in skin tone and wardrobe
Have you any advise or previous posts I could revisit ?Isabella says:
I was a lifetime brunette, who is going grey – but only very slowly, and not evenly, the rest of my hair is turning a sort of dark iron – no tonality, no light. So have resorted to blonde highlights, keeping the grey showing. The long term plan is that when there is enough grey I will reduce the blonde until I no longer need it. Some days I wish it were dark again but I remember the long term plan and stick with it. I have olive skin and brown eyes. The colour thing has definitely impacted me too. I think more colour is needed when your hair no longer provides it. Grey and navy are my go to colours – black only when there is a scarf or bright top underneath to lighten. Otherwise bright blues, oranges and stripes are my highlight colours.
I looked at the app recommended (stylebook) I may give it a trial but if it needs me to be on my phone too often have a rethink and adopt Lucinda’s notebook tip – and add photos.
Thank you, Barbara and Maudie for tips about where to find cargo pants at a good price. I’m off to check them out ! And I echo all the above who love and find TNMA such an inspirational blog !
I’ve struggled through growing out all brown hair dye. My hair is now dark brown mixed with grey streaks with lighter bits round the face. For makeup I find you need warm colours in blusher. Present favourite is Chubby stick by Clinique in Rhubarb and a Rosy one. Sometimes mixed together sometimes just one. And lipstick to brighten the face. Warm colours round the face add warmth to complexion also. All the Reds, peach and orange tones work well as does sunflower yellow colour popular now.
I’m intrigued to hear about apps to help plan outfits. I don’t use these nor notebooks to record combinations. But I do rely on trial and error and experimenting with combinations. I do hang things together so I can easily coordinate an outfit. And hang scarves with the corresponding colour jacket or top so it’s easy to put my hand on the right one/ones. I use many coloured scarves to pull an outfit together picking out a colour. It mixes things up a bit, is a quick way to personalise an outfit as well as keeping me warm in this up and down weather.monique J johnson says:
I’m 58 and really enjoy your blog.
I’m trying to help my 84 year-old mother-in-law lose her fear of shopping. She is a “plus-sized” lady, intelligent and funny, and she wants to dress better (I won’t even go into the disaster of beige polyester that is her wardrobe) but has no inspiration. Her insecurities keep her from going shopping, and she isn’t facile on the computer. Also, unlike me, she hasn’t yet learnt the true value of a good tailor, but I’m working on that.
Can you suggest any bloggers in her age range who are on the heavier side? She’s not going to turn into The Accidental Icon or Iris Apfel, she’s far more conservative, but there must be someone out there who is a little more… uh…. regular, I guess. Please help!
Thanks.
Nicole K says:
Hi Monique-I’m in the US but follow Chic At Any Age – Josephine is not larger sized but I would say her style is a little less edgy than Alison’s and might appeal to your mother-in-law for ideas? Lots of simple, loose silhouettes and advice on accessories and color.
Oh, EXCELLENT! I just checked out that blog. Thank you so much. It’s perfect!
BTW – I’m in the states too, Marina del Rey, CA to be exact. Mom-in-law is in Vancouver.
Thanks again. That was very helpful.
Rachel Griffiths says:
Agree agree. I was out walking the dog in 501’s rolled up at the ankle, white hi-tops and a navy linen jacket this morning and wondered why it felt so right. It’s because it’s my “can’t go wrong’ look!
Meanwhile, can anyone help me with putting up thinning hair (age 51). I have very thin hair in a long bob (almost touching shoulders) . I used to put it up in a chignon with a barrette clip all the time but I don’t have enough hair now! I’d love some style tips on relaxed up-dos for thinning hair.
Thank you
RachelGillian Gustar says:
I love your blog – for the inspiration, honesty and encouragement to be who we are – not who some fashion pundit would like to make us think we could/should be. I’ve stopped apologizing for having a wardrobe full of merino wool jumpers and silk shirts which variously are worn with trousers/jeans – sometimes almost school uniform style – and started focusing on fab jackets and shoes to jazz them up. A recent visit to Harris found me buying the most fabulous purple tweed and velvet jacket (not a fabric I’d have tried before) – but it lifts every pair of black trousers/jeans in my wardrobe……so thank you!!
I second the last comment. I have bought less, worn my clothes in different combinations, and found new love for old stuff. You ARE an inspiration, in giving us all the confidence and extra ooomph to dress in a way that suits our individual style and personalities. Cheers!
Just found this blog and my heart feels so happy!
Finally, a community of funny, smart and kind women in my age cohort (58) who understand that clothes matter because they to us and others About us.
The narrative should honor our lives, joys, travails and our feminine beauty which is ageless. We are at this age kinder and more graceful than when we were young.
Especially to our own dear selves.
Thank you all,
Isobel 
Stephanie 
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Great advice, all of it. A question that is related to cargo pants only is how tall are you? I love your look here, but I may be too short to wear them.