Dressing for Your Lifestyle, Part 1

Posted by Jill Chivers in Shop Your Wardrobe Strategies

I’ve been asked to write something about dressing, and finding a style, that suits your life/style.  The life/style you have now – not a past life/style, or a future or fantasy life/style.

A wonderful topic, because one of the reasons I believe our wardrobes are stuffed to the gills with gear we aren’t wearing is because:

  • We don’t have enough stuff we love to wear – it may work well on paper, but something about those items doesn’t call to us, we don’t adore those items
  • We have too many items that fit a life/style we used to have – our wardrobes are reflecting our pasts, not our presents
  • We have too many items that are ‘aspirational’ – items we’ve purchased for a life we perhaps we like to have, or someone has told us we should want to have.  But we don’t actually have this life/style

I’ve written about this before, but let me go into this topic with some greater depth in this two-part article.

I’ll start by giving you a couple of examples from my own life and wardrobe.

The Suit vs. The Wrap Dress

Which outfit suits the life/style I have now?

Which outfit suits the life/style I have now?


These are two items I’m very familiar with.  In times past, my wardrobe had many items in it like the suit on the left.  The times when my wardrobe was full of these items was when I was:

  • an employee for a global accounting and advisory firm, working in a client-facing professional role that required me to be on client sites, have client meetings, deliver client deliverables and generally represent the firm I worked for in a highly professional manner.
  • running my own facilitation and training firm full-time, working for high-end, global clients who had a set of expectations about how professional I was, which included (however unspoken or subtly) how I presented myself.

My work/life doesn’t include either of those things now.  Right now, much of my time is spent working from home, in my home office.  I still see clients, but in a different way.

There’s no place for such a formal corporate suit, like the image on the left.  That’s the life I used to lead – not the one I’m leading now.

The life I’m leading now lends itself much more to a casual combination of items, a more relaxed way of dressing and expressing myself.

The life I have now is suited more to the jersey wrap dress on the right.  That’s the life I’m living right now.


The Pump vs. The Mule

Which shoe suits the life/style I have now?

Which shoe suits the life/style I have now?

Here are another two items I’m very familiar with.  I purchased and wore many a shoe over my corporate career that resembled the shoe on the left.  They went with the suit in the image above.  Suits and high heel pumps go together, and they went with the work I was engaged in and the life I was leading in times past.

But I’m not living that life anymore.  I’m living a more relaxed life/style, in every respect.  There’s very little place for a shoe like the one on the left in my life right now.

Which is why when I purchased a shoe very similar to this a year ago (a very expensive shoe in an exclusive Sydney shoe boutique), I went through a set of mental and emotional machinations (guilt, disappointment, frustration – all aimed at myself) for buying such a ridiculous item that clearly didn’t fit my life/style – the one I have now.

The shoes on the left are for a life I used to have.  They are shoes from my past.

The shoe on the right fits the life/style I have right now.  I live in a tropical climate where we have a version of summer at least half the year, sometimes up to 9 months of the year.  I work in my home office much of the time, and even when I’m not, I’m often seeing local clients who are dressed in a very relaxed style.

Sure there are occasions in my current life where I wear the shoe on the left – just not that many in comparison to the occasions in my life where I would have call to wear the shoe on the right.


For a Life/Style Some Might Aspire To (but don’t really lead)

And just to complete the picture, above are items for a life that, if I were to take to heart many of the “reality” shows on cable television, I might believe I needed to have in my life, if I were to aspire to the lives of women we are supposed to admire, even envy.

(For complete clarity, I have no such aspirations.  But I thought it would be instructional to do the “past”, “current” and “aspirational/fantasy” looks that explain why so much of our wardrobes don’t work for the lives we are living now).

I don’t have a life/style where either of the above items would ever be worn.  So why would I purchase items like this?  Seems crazy, but I meet many women who do buy items for a fantasy or aspirational life/style.  They either fall in love with the item because it’s gorgeous, or they have somehow come to believe that if they buy these items, their lives will transform in some way that will cause these items to become necessary.

And there’s a lot of images on television and in the media in general that send the message that women dressed extremely glamorously and expensively are women whose lives we should admire, aspire to, envy.  Reality television shows on cable, in particular, show us images that to my mind are absolutely unrealistic, with “real housewives” out to lunch  dressed in ensembles resembling the glitzy gold numbers here, hair and make-up done to a level that only a professional could achieve with a few hours in a salon, with other women similarly turned out.

See how this works?

It seems so very obvious, I know.  But it’s amazing when you apply this to your own wardrobe, your own life, your own style, how often you can trip yourself up by buying for a life, and a style, that isn’t really yours.

In Part 2 of this article, I’ll share my 3 steps for dressing for the life/style you have right now – not a life/style from your past or possible future.


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