Retirement Wardrobe: How to Dress for the Life You’re Living Now

There are some changes that come with moving towards retirement that we expect.

We know our working hours might change. Our routines will change. We might have more time at home, more freedom in our days and hopefully a little more choice about how we spend them.

What I hadn’t really considered was that my wardrobe would need to change too.

Since I started working more flexibly from home, my days look very different to the way they did ten years ago. I’m home much more. I don’t need a wardrobe filled with traditional work clothes anymore, and the clothes I reach for need to work for a much more relaxed and flexible life.

It sounds like such a small thing, but for a while I hadn’t quite caught up with that.

My life had changed.

My wardrobe hadn’t.

When Your Old Clothes Belong to Your Old Life

Initially, I simply kept wearing many of the clothes I’d always worn for work.

There was nothing particularly wrong with them. In fact, I had some lovely clothes.

But somehow, whenever I put them on, I didn’t feel quite right.

They were clothes for a version of my life that didn’t really exist anymore.

At the same time, spending the day at home in very casual clothes didn’t feel particularly like me either. I love being comfortable, but I’ve realised that I also like feeling pulled together. There is something about getting dressed properly in the morning that makes me feel ready for the day, even if that day involves working at my desk at home, running errands, meeting a friend for coffee or doing jobs around the house.

I needed to find the middle ground.

And, as you may have gathered if you’ve been following this retirement series, when I don’t know the answer to something, I tend to research it!

So down the rabbit hole I went.

What Does My Life Actually Look Like Now?

I started reading about clothing and style for women over 50, looking at outfits I liked and trying to work out what it was about them that appealed to me.

But the most useful thing I did wasn’t finding a list telling me what women my age should wear.

It was looking at my own life.

What did my days actually look like now?

Where did I go?

What did I spend most of my time doing?

How did I want to feel in my clothes?

And perhaps most importantly, how did I want to feel about myself when I got dressed?

Instead of trying to create a wardrobe for some imaginary lifestyle, I started thinking about the life I was actually living — and the life I wanted to live as I moved closer to retirement.

That made things much clearer.

I Finally Put a Name to My Style

After all that research, I realised something incredibly simple.

My style is smart casual.

It probably always has been.

I’ve never felt completely comfortable when I’m very dressed up, but I don’t particularly like being really dressed down either.

I’m happiest somewhere in the middle.

In winter, that usually means jeans and blazers, comfortable easy-care jumpers, sneakers and boots.

In summer, I’m much more likely to reach for linen dresses, white linen pants and darker linen tops, usually with sneakers or comfortable sandals.

And I’ve just noticed how often I’ve used the word comfortable.

Perhaps that sums up this stage of my life better than anything else.

I want a comfortable lifestyle and I want comfortable clothes to go with it.

But comfortable doesn’t have to mean that I’ve stopped caring about how I look. For me, it means clothes that feel good, fit my real life and still make me feel like myself.

Letting Go of Clothes That Weren’t Really Me

When I took a proper look at my wardrobe, I realised it had become a bit of a mishmash.

I’ve always gravitated towards good-quality, classic clothing — usually bought on sale or discovered in an op shop. Those pieces have generally served me really well because they don’t date quickly and they tend to work with lots of other things.

But mixed in amongst them were random trendy purchases I’d collected over the years.

You know the ones.

They look fabulous on somebody else. You convince yourself you’re going to become the sort of person who wears them. And then they spend the next three years hanging in the wardrobe while you reach around them for the same pair of jeans you’ve worn approximately 400 times.

When I really thought about it, those pieces had never felt like me.

I had bought clothes for trends, occasions, previous versions of my life and sometimes even for the person I thought I should be.

What I wanted now was a wardrobe for the person I actually am.

Creating a Capsule Wardrobe for the Life I Have Now

That’s when I decided a capsule wardrobe made sense for me.

I didn’t want a tiny wardrobe where I owned twelve pieces of clothing and somehow magically created 47 outfits from them. That’s probably never going to be me!

What I wanted was a wardrobe where most things worked together.

A collection of clothes I genuinely liked wearing, suited my lifestyle and could be mixed and matched without too much thought.

The first step was a big cull.

I looked at what I actually wore rather than what I thought I might wear one day.

I kept the beautiful classic pieces that still suited me and my life. I let go of things that no longer fitted properly, things I hadn’t worn for years and those random trendy purchases that had never really felt right.

Then I started looking at what was left.

Be Honest About What Really Deserves a Place in Your Wardrobe

I think this part requires a little bit of brutal honesty with yourself too.

If you have something that needs mending, ask yourself whether you genuinely love it enough to actually mend it. If you have a beautiful piece that no longer fits properly — something I found myself dealing with after losing some weight — is it worth having it altered so that it fits you well again?

Sometimes the answer will absolutely be yes.

But sometimes we hold onto things because they were good pieces rather than because they are still right for us now.

Take a black blazer, for example. Perhaps you’ve owned it for years and it was once a wardrobe favourite, but now the fit isn’t quite right, the shape is looking a little dated or it would cost almost as much to alter as it would to replace. Maybe the better choice is to let that one go and, when you find the right one on sale of course, replace it with a blazer that fits beautifully and feels a little more current.

The same goes for the everyday things.

Do your jeans constantly need a belt to stay up? If they do, do you actually like wearing belts? Do you even own belts that work with them? Or do your jeans fit perfectly when you’re standing up but dig into you the minute you sit down?

These sound like tiny details, but they’re exactly the things that determine whether we actually reach for an item or continually push it aside.

I found it helpful to ask myself the harder questions.

Do I love this enough to repair it?

Would I pay to have this altered?

Does it fit comfortably right now?

Do I genuinely enjoy wearing it?

Would I buy it again today?

And perhaps the most revealing question of all:

Am I keeping this because it suits my life now, or because I’m remembering the life I wore it in?

Being honest can mean letting go of some lovely things, but I promise the end result is worth it. A wardrobe filled with clothes that fit properly, feel comfortable and genuinely suit you is so much nicer than a wardrobe full of clothes that are merely almost right.

Finding the Colours That Work For Me

One of the things I learned while researching capsule wardrobes was how helpful it is to have a fairly consistent colour palette. But rather than choosing colours because somebody told me they were the colours I should be wearing, I looked at the colours I’d naturally been drawn to for years.

Black was an obvious starting point. I’ve always loved wearing black. It makes me feel put together even if I’m just wearing leisurewear around the house. I also love navy and denim, taupe and caramel, white and, more recently, chocolate brown. I wear gold jewellery and find all of these colours work beautifully with it, so they became the foundation colours for my capsule wardrobe.

Then I wanted to add a little more interest without ending up with lots of colours that didn’t work with anything else.

I chose two colours I naturally gravitate towards — olive green and pink. Both work beautifully with the basics I already wear and give me enough variety without making my wardrobe feel disjointed.

Your choices, of course, might be completely different. You may love many of the same neutral basics but naturally gravitate towards light blue and red instead. They would work just as well, but suddenly the wardrobe would feel much more like you.

And having a colour palette certainly doesn’t mean everything needs to be plain.

I still love some pattern. Animal print has always appealed to me, and in summer I might choose a pretty floral linen dress. I just try to keep those patterns within the same general colour family so that they still work with the shoes, jackets, bags and accessories I already own.

That’s really what I’ve come to love about having a colour palette. It isn’t about creating rules around what I can and can’t wear. It’s simply about making sure that when I bring something new into my wardrobe, there’s a very good chance it will work with several things I already own.

Suddenly, instead of owning lots of individual clothes, I was beginning to have outfits.

And that was a big difference.

Straight From My Wardrobe

A little note about the flat lays you’ll see throughout this article — every piece I’ve used comes straight from my own wardrobe and is something I genuinely wear. I could have created perfectly styled flat lays using beautiful new and expensive clothing, but that didn’t feel quite right for this post. I wanted to show you what a real-life wardrobe looks like when it’s built around the clothes that suit your lifestyle, personal style and budget. Some of these pieces I’ve owned for years, some were bought on sale and others have been wonderful op-shop finds. Because they’re my own clothes and many are no longer available to purchase, unfortunately I can’t link the individual outfits — but hopefully they give you some inspiration for creating similar combinations from pieces you already own.

Where I Like to Shop

While I can’t link most of the individual pieces in these photos, I thought it might be helpful to share some of the brands and stores I find myself returning to again and again.

For jackets and knitwear, Sportscraft and Trenery have been favourites for years. Some of the pieces I own from these brands have been in my wardrobe for more than ten years and are still going strong. I’ve even found some beautiful Sportscraft jackets at Vinnies — one of the advantages of buying classic styles is that they don’t tend to date quickly, which also makes them wonderful pieces to look for secondhand.

For linen, I often find great pieces at TK Maxx, Country Road and Sussan. I tend not to spend a fortune on everyday linen, particularly pants, because I’ve found they can eventually wear thin with regular use. I might spend a little more on a beautiful linen dress, though. Often it will begin life as something I wear for lunches and special outings and, after a few years, gradually become one of my favourite dresses to wear at home. I love that progression — good clothes don’t necessarily need to be discarded simply because they’re no longer our “best”.

For more special pieces, I’ll happily shop around. Myer, David Jones, Blue Illusion, Adorne and various online retailers have all found their way into my wardrobe. But if I’m buying something very specific — a wedding guest outfit, for example — I’m particularly determined to find a bargain. If I know something isn’t going to get a lot of wear, I find it difficult to justify spending a fortune on it.

Shoes are another area where I’ve found a few brands that consistently work for me. Django & Juliette is probably my go-to, but I also love Diana Ferrari and Midas, and I’ve recently become a fan of VIVAIA. At this stage, comfortable shoes are absolutely non-negotiable, but thankfully that no longer means they can’t look good too.

And then there are handbags.

I’ve been an Oroton girl for decades. I don’t think the quality is quite what it was twenty years ago, but I still love their bags. I generally choose classic styles that I’ll use for years, although a handbag is one place where I’m quite happy to introduce a pop of colour.

I will admit I have a bit of a weakness for bags.

But I’ve decided there’s a perfectly reasonable explanation for that — a fluctuating body doesn’t affect the fit of your handbag!

At least that’s the excuse I’m sticking with.

Investing in the Pieces I Wear Again and Again

I’ve also become much more conscious of buying fewer things but choosing them well.

A great blazer.

Jeans that fit properly and feel comfortable. Not always easy to find I know.

A beautiful linen dress.

Good-quality knitwear that’s easy to care for.

Comfortable sneakers, boots and sandals that I can actually walk in.

Simple tops that work with several different bottoms.

These aren’t particularly exciting purchases individually, but together they create the backbone of my wardrobe.

Because my style leans towards classic pieces anyway, I’d much rather buy something good quality on sale — or find a wonderful secondhand piece — than continually buy cheaper clothes simply because they’re fashionable.

I’m learning to ask myself a different question when I shop now.

Not simply, “Do I like this?”

But, “Will I actually wear this in the life I have now?”

That’s a much more useful question.

Leaving Room for a Little Personality

Of course, I don’t want my wardrobe to become so practical that it loses all personality.

That’s where accessories and a few more interesting pieces come in.

A scarf, jewellery, a lovely handbag, an interesting blouse or even a great pair of shoes can completely change a simple outfit.

The difference now is that I want those pieces to work with the clothes I already own rather than becoming another random purchase hanging on its own in the wardrobe.

I’m trying to be much more intentional about what comes home with me.

I’m not always successful — let’s not get carried away here — but I’m definitely getting better!

Perhaps Our Wardrobes Need to Retire Too

The more I’ve thought about this, the more I’ve realised that changing my wardrobe has actually been another small part of accepting that my life is changing.

And I don’t mean that in a negative way.

Quite the opposite.

There is something rather lovely about no longer needing to dress for a life that doesn’t suit me anymore.

I’m not trying to recreate the wardrobe I had ten or twenty years ago. I’m not particularly interested in dressing “younger”, and I’m certainly not ready to disappear into clothes simply because I’ve reached a certain age.

I just want to look like me.

A slightly more relaxed version of me.

A woman who likes beautiful things but also wants to be comfortable. Who loves a blazer but wants to wear it with jeans and sneakers. Who appreciates good-quality clothes but also gets an enormous thrill from finding them in an op shop.

And perhaps most importantly, someone whose clothes fit the life she’s actually living.

Dressing for Days That Move Between Home and Life

Another thing I’ve realised about this stage of life is that although I’m spending much more time at home, I’m actually in and out of the house far more than I used to be.

My days aren’t as clearly defined as they once were. I might spend the morning working at home, then pop out to pick something up, visit someone, meet a friend for coffee or run a few errands before coming home again.

I don’t want to have to change clothes every time I walk out the front door simply because I’ve been wearing my “house clothes”.

That’s another reason my version of comfortable has become so important to me.

I want clothes that are comfortable enough to wear around the house for several hours but still make me feel put together enough to head out without giving it another thought. Jeans and a soft knit, linen pants and a simple top, or an easy dress with sneakers all work perfectly for the way I live now.

In many ways, I think that’s what I was missing when I first started working more from home. I was still dressing as though my day had to fit into one category — either I was dressed for work, dressed to go out or dressed to stay home.

My life doesn’t really work like that anymore.

And now, neither does my wardrobe.

Dressing for the Life Ahead

Retirement, or even the transition towards it, asks us to reconsider so many things.

How we spend our time.

What gives us purpose.

How we look after ourselves.

The kind of home we want to live in.

And, apparently, what’s hanging in our wardrobe.

I’ve realised that accepting our changing life isn’t about letting go of who we were.

It’s about taking the parts of ourselves that still feel right and allowing the rest to evolve.

My wardrobe hasn’t become less important to me.

If anything, it feels more like me than it has in years.

There are fewer clothes competing for my attention, more things that work together and far fewer mornings spent staring into a wardrobe full of clothes thinking, I have absolutely nothing to wear.

I’ve finally found the place somewhere in between that feels right for me.

And at this stage of life, I’m very happy to stay there.

If you’re new to my Retirement Reflections series, you might like to start at the beginning with When to Start Planning for Retirement: The Simple Mistake Most People Make, where I share why I believe preparing for this next chapter needs to begin long before our final day at work.