What to wear to Wimbledon: stylish and comfortable outfit ideas for women over 50 this summer

It’s summer event season here in the UK and there are two big dates on the calendar very soon: Royal Ascot in early June and Wimbledon at the end of June. I’d love to be going to both, or either to be honest, I’m not fussy!  No plans as yet sadly, but if I was going, this is exactly the sort of dress I’d be wearing. And I absolutely plan to find another reason to wear it this summer. So, with that in mind, here is a little tennis style inspiration.

Wimbledon is one of those lovely British summertime events that allows us to dress up a little. It is an excuse to wear the dress, add the accessories and make a bit more effort, but without forgetting the most important things: feeling comfortable, confident and fabulous.

There is no strict dress code for Wimbledon, although smart-casual attire is recommended. And really, why would you want to dress down when it is the perfect excuse to dress up? If you are lucky enough to have tickets for the Royal Box, a smarter look would be expected. I always love looking out for the Princess of Wales during Wimbledon, she gets it right every time and is a wonderful source of classic summer style inspiration for me.

​This blog post contains paid for links.

Outfit inspiration for Wimbledon for women over 50

Why Wimbledon is such a British tradition 

Wimbledon is the oldest and most famous tennis tournament in the world, held every summer at the All England Club in south-west London. It is known not just for world-class tennis, but for its very British traditions too, from strawberries and cream to the all-white dress code for players. For many of us, Wimbledon has become part of the summer season, whether you are lucky enough to be there in person, watching at home or simply taking a little inspiration from the fresh, classic tennis style.

Start with comfortable shoes

A day at Wimbledon can be a long one and often involves far more walking than you might expect, so footwear really matters. I would always start with the shoes and build the rest of the outfit from there. Thank goodness we can now wear trainers, or tennis-inspired shoes, with dresses and still look smart, modern and pulled together.

Gone are the days when I would suffer through a full day in heels that looked lovely but were hurting by lunchtime. For any summer event now, I always think about footwear first. If my feet are comfortable, I feel so much more confident.  How the Princess of Wales manages in her heels I will never know!!

For Wimbledon, I would recommend a pair of classic trainers or take inspiration from tennis shoes, flat sandals or a pair of espadrille wedges, depending on your outfit and how much walking you expect to do.

I am wearing my Stan Smith Shoes from adidas, an authentic version of the 1970s tennis classic originally created for tennis star Stan Smith. They are one of those styles that never really go out of fashion. Made from full-grain leather, my pair has the red heel detail and an OrthoLite sockliner for extra comfort.

And did you know that they way we wear trainers has changed completely, and they are now the backbone of everyday dressing.  Perfect with tailoring or occasion wear, trainers are replacing traditional footwear in ways that reflect a broader move towards comfort-led style according to TK Maxx who have identified the key ways trainers are being styled right now.  
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And if you are a tennis player yourself, Wimbledon season is also the perfect excuse to refresh your tennis clothing and get into the spirit of summer on court.

I'm styling my cherry print shirt dress with my adidas stan smith tennis shoes

Wimbledon style inspiration 

When I think of Wimbledon style, I always think of fresh, classic colours: whites, creams, navy, soft blue, fresh green and just a little pop of red. It is a colour palette that feels smart, summery and very easy to wear, whether you are actually heading to Wimbledon or simply taking inspiration from that timeless tennis look.

You do not have to wear all white or look as if you are about to step onto Centre Court. It is more about choosing pieces that feel fresh, polished and comfortable, then adding your own personality with accessories, colour and layers.

Here are a few Wimbledon outfit ideas to inspire you.

The summer dress
A summer dress is probably one of the easiest Wimbledon outfit options, especially if you want to look dressed up without feeling too formal. Cotton, linen or a linen-mix all work well, although I must admit I prefer a linen blend as I am not a fan of too much creasing.

Add a pop of colour with a crossbody bag or a tote, especially if you need room for a light jacket, sunglasses, SPF and the inevitable umbrella. I am wearing a midi shirt dress in stretch cotton in this stunning cherry print, from the new collaboration between Helene Berman x Katy Pullinger for QVC. It feels fresh, feminine and event-ready, but still easy enough to wear with trainers or comfortable sandals.

White jeans or wide-leg trousers with a blazer
White or ecru jeans are such a good option if the weather is looking a bit uncertain, and let’s be honest, that is always possible in June. I love the idea of white jeans or wide-leg trousers with a navy polka dot blouse, a blazer and a fine-knit worn over the shoulders. Take a look at my M&S jeans recommendations for fabulous denim.

It is smart but still relaxed, and it gives you those all-important layers without feeling too heavy. This is the sort of outfit that would work beautifully for Wimbledon, but also for lunch with friends, a summer party or a day out where you want to feel a little more polished.

Tennis-inspired separates
This does not mean turning up in your sports kit, unless you are actually playing of course. Think more along the lines of a polo-style top, a pleated skirt, tailored shorts or a simple white T-shirt worn with a blazer.

It is a lovely way to nod to the tennis theme without feeling too dressed up or too sporty. Browsing tennis clothing can be a great starting point for inspiration, even if you then translate the look into more everyday pieces. A crisp white top, a navy layer, a pleated shape or a clean pair of tennis-inspired shoes can all give a subtle Wimbledon feel.

Don't forget accessories
Accessories can make a simple outfit feel much more event-ready. A big statement pair of sunglasses is always a good idea (mine are by Ahlem from CBTR in Beaconsfield), and I would also recommend a proper sun hat, ideally UPF50+, if you are going to be outside for much of the day.

A matching or toning umbrella is another very British essential, and a lightweight scarf can be surprisingly useful too, either for sun protection or a bit of warmth later in the day. And then, of course, you need a fabulous bag that can carry everything easily without feeling too bulky. A crossbody, roomy tote or smart basket-style bag would all work well.

Make sure you have layers
We all know what the British weather can be like, changeable at best. Wimbledon in a heatwave is possible, but so is Wimbledon in torrential rain. You may be sitting in shaded seats, standing in full sun, travelling on an air-conditioned train or melting on a busy underground journey.

So layers are your friend. A blazer, trench coat, cardigan or lightweight knit will all help make your outfit more practical, while still keeping it stylish. For me, the best Wimbledon-inspired outfits are the ones that look lovely but also work in real life, because feeling comfortable is what allows you to relax and enjoy the day.

And not just for Centre Court!

My outfit would work just as well for Royal Ascot (with a different hat) as it would for Wimbledon, or maybe, like me, you do not actually have any summer event plans in the diary yet. But that does not mean we cannot take a little inspiration from the season.

You might be watching Wimbledon at home, meeting friends for a tennis-themed lunch, going to a summer garden party, a BBQ or simply looking for an excuse to wear something pretty. There are always lovely summer moments when a dress is perfect!

This dress works equally as well with my comfortable block heel red sandals from Air & Grace

My red sandals are from Air & Grace and have extra cushioning and a wide band to make them very comfortable to wear all day.  My bag is from Sarah Haran (use FIFTYANDFAB to get 20% off your first bag (and three free accessories).

My favourite outfits are the ones that help me feel confident and comfortable. I always prefer a dress in the summer but white jeans with a relaxed shirt, a light jacket for changeable weather or a few tennis-inspired details can feel stylish too.

And that is the joy of summer dressing over 50. We do not need to dress younger or overly sporty to enjoy the look. We can take the parts we love, make them practical and wear them in a way that feels easy and elegant and exactly like us!
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Love from
Michelle xx


​Disclaimer: this blog post contains paid for links, my dress was gifted to me as part of a separate collaboration.