How to Develop Your Style as You Age


How to Develop Your Style as You Age


Recently I was asked a question about how to deal with and embrace style as you go through midlife into older age with the many changes that happen to us, from lifestyle to body and colouring.

My aim is that you still enjoy the process of dressing and style with maturity even though the media can make many of us feel that fashion is only for the young, and slim.

In this video with Jill Chivers of Shop Your Wardrobe we discuss elements of ageing, bodies and lifestyle influences.


We also discuss other aspects of style as you age including:

  • How to find the positives of ageing.
  • Embracing the changes of lifestyle which have different wardrobe needs.
  • How to find clothes that still make you feel smart but not corporate.
  • Letting go of what no longer serves you in your wardrobe.
  • Learning how to dress the body you have today which may have changed with age (and have a whole new set of rules to learn and internalize).

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  • A very timely post Imogen and Jill, thank you. I took early retirement in February this year and still find it difficult to go past stores like Rhodes and Beckett without thinking I should pop in to check out their corporate clothing! As a “classic” dresser I’ll never be one to go totally casual and finding that medium ground has been a challenge. I always joked that I’d be wearing pearls to do my house cleaning. At the moment I have kept one suit for corporate events I still attend occasionally, but it’s all a learning curve, that’s for sure.

  • You two make such a fantastic team! I am probably among the older of your readers so this video is especially pertinent for me. As a member of the 7 Steps to Style program and Evolve your Style, I have learned so much about dressing for the person you are currently. Although we may never be the way we looked in our 40’s, 50’s and 60s + etc., we can certainly look great and take pride in how we look today.

  • I loved this video for many reasons — not the least of which is your genuine camaraderie and friendship, which is such a pleasure to see.

    I also appreciated your discussion of how our bodies change and how comfort can become more important, esp as it relates to tight things around the waist! At about age 50, I said no more, and now put a loose, comfortable waist and overall fit at the top of my list. No more tourniquets around the waist, LOL.

  • As a crone I love this discussion! No “decent into misery” for me! Jill, you look the best ever in that blouse!

  • In menopause I loved softness in my clothes …but now I feel the need for structure again as I am old.

  • Super video! Yes, transitioning was (is) hard, and going from waisted to non-waisted? It never occurred to me that would be part of the aging process. Funny to see all the jewelry lately, that highlights the neck – all those chokers – and to consider how fashion trains the eye on body parts that show age! And yes, I am still drawn to dresses, which I find nowadays usually do have pockets. I have to pass most of them by because I just don’t live in dresses nowadays. But it’s hard for me to whittle my wardrobe down. I love this train of discussion!

  • Thank you for this timely video. I’m in the middle of this transition phase. I was made redundant about a year ago, at age 60. Although I worked in an office, it wasn’t a corporate environment. I lost interest in my work over the last few years, and, as this happened, I found I dressed more and more casually. I’m hoping not to have to return to the workforce, but am struggling to part with my “smarter” clothes (and the shoes! Oh my goodness – the shoes….and the boots….and the handbags….!)
    My waist has also got thicker with age, which I’m struggling to accept (I used to be an hourglass). I wish there was a “magic pill” for that one, so I was interested to hear what you said about oestrogen and the thickening waistline!
    Thank you.

  • Interesting video. As one who has never been in the corporate world, I love stiff fabrics (and the other extreme — floaty diaphanous silks) and have an aversion to the stretchy and wrinkly medium-weight fabrics you seem to be suggesting might be preferable once one has left the corporate world. I don’t think my look is corporate, but perhaps you would think it is, given that I like to look neat and tidy and dislike what seem to me very casual outfits. I don’t wear suits, as such, but I do wear dresses in high-quality stiffer fabrics. I tend to wear silk scarves and smart, feminine leather jackets. When I first started dressing more in accordance with how I myself prefer to dress, I felt self-conscious when I got comments on my clothes, but now I hardly notice them. For me, style has become easier and easier over the years, as my confidence has grown. In youth I was always so worried about what people would think, but now, well, thankfully, that is not something that weighs on me any more. I just wear what I like. You might find my look “corporate” but I promise you, it is definitely not a question of clinging to a corporate youth, or failing to embrace my age. Not that I particularly agree with the idea that one should embrace age, any more than one should embrace youth. Age is just age. To me, it is more about embracing the person you are as an individual, with your own unique personality, ideas and preferences, rather than embracing our age.

  • Such a helpful, insightful discussion. Thank you. Learning to dress the ‘new’ me in retirement, has been/is, as you commented, hard work. You covered how one’s body shape changes; so true. Add mastectomy to the pot & it’s definitely a challenge. But by reading/listening to folk like yourselves it’s a challenge in which success is sweet indeed. When are you going to address the comfort factor in underwear, especially in bras for older women? (I’m not overweight but require a bra extender as does my sister who’s slimmer than me.). Wonder if other women notice this.

    • Bras! I understand they can be so tricky to find ones that are comfortable. There are so many different breast shapes and placement on your torso, and this means that different brands will be more comfortable for different people – some have wider spaced cups, others closer – like anything there is not magic formula or brand that will suit everyone, and it’s often a matter of trial and error in trying on to find the ones more comfortable for you.

  • Hello Jill and Imogene,
    I have been following you both for quite a while as I am going through this process – and it is a process! I am a petite classic and yes my hair has gone from brown with golden highlights to silver. Huge changes in appearance but also in who am I now? I think that has been the biggest block to moving forward as I haven’t a clue as to who I am/want to be now. It’s been 3 years and slowly, very very slowly glimpses of the new me are coming through. I’ve had to lighten and soften my colors and my clothing but I am too short to be much of a “boho.” I keep saying a soft classic natural but it is still very fuzzy – this conversation is one I hope continues for a long time. I suspect there are more changes ahead. Thank you both.

  • Another great video, many thanks! Been a bit confused over last 2 years, retired early as husband sold business and we had big move from England to Scotland, new house, new friends, etc, etc. Went through a funny stage of wearing all sorts of things bought in bargain shops and sales to try and find myself again, don’t laugh! Tried different colours, different styles and new looks all to no avail. New friend convinced me that I should be classic like her, so even bought an expensive designer coat, fortunately it is padded and hooded for the Scottish weather as well as great fit and basic black, but not convinced now it was the best way to spend money.
    Eventually saw a style consultant, thank God, who said I had gone from dark autumn to bright spring, wouldn’t have believed it until saw it with own eyes in the mirror too! She was as surprised as me, so all my brown stuff, which to be honest, hadn’t looked good for a few years, now gone to charity. I didn’t work in a corporate setting, no suits or formal skirts or shoes, taught art and design in a college, and to be honest don’t like stiff clothing in look or feel, so why I was persuaded to try classic by friend is beyond me, it was her, not me at all. Trying to get away from black at the moment, which is a bit deadening on the skin now and cultivate an arty (concentrating on own artwork now) laid back look with contemporary feel to fit in with new colours.
    It was a tricky stage of life and not totally there yet, but I think nearly every woman has to face these transition periods in life; it will come right in the end I am sure, as long as it remains fun trying and don’t allow myself to get too anxious about it all.

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