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What to wear when you start dating over 50

Article by Ceri Wheeldon

When it comes to dressing for your dating journey it is best to be prepared! The last thing you want when you have a date in the diary is to panic about what to wear. Better to plan ahead.  I was watching an old episode of friends recently where Rachel was accusing Monica of ruining her ‘third date sweater’. So we know that she planned her  dating wardrobe!!

I spent many years working as a headhunter, and always suggested to my candidates that they planned their wardrobe for a minimum of 3 job interviews, so I suggest you put together at least 3 different outfits to suit the sorts of places you would envisage going to on a first date, and 2 outfits for a second date. Remember that your date’s picture of you in his mind before meeting will be based on the photos you have posted with your profile, or what you were wearing when he met you socially. Aim to wear your best version of that.

If you are looking super chic then that is how he is expecting you to look when you walk through the door. If you are looking casual in your picture while walking the dog…then dress along similar lines.

Here are just some suggestions to put together your capsule dating wardrobe. First impressions count. You want to live up to the expectations set by the photo in your profile, and you also want to feel comfortable and relaxed. No fiddling with hemlines or necklines. Remember that once you have walked into the venue and sat down, it will be your top half that will be on show. Similarly, a fabulous coat , while making a good initial impact is likely to spend most of your date hanging up.  Prioritise tops and accessories.

Capsule wardrobe for dating over 50


Mix and match. As we said, it’s your top half that’s on show for 90% of the time. Think colour, neckline, sleeve length and jewellery.

I would put together smart trousers  (or a skirt if you prefer) , smart jeans, 2 dresses – one for day and one for evening, 3 tops , 2 pairs of shoes (or one pair of shoes and boots in winter) and a jacket or coat.

Here are some suggestions:

A pair of  ankle skimming tailored black trousers – very versatile and great with kitten heels or flats. This particular pair is by Hobbs at John Lewis Full details

what to wear on a date over 50 black trousers




Classic Jeans by French Connection from House of Fraser Full details

what to wear on a date over 50 jeans


A simple floral skirt from Boden full details

What to wear on a date over 50 skirt image


Black pencil skirt with a twist from Damsel in a Dress. I love the full length zip feature on this one. full details

over 50 black pencil skirt image

skier with side zip image



Splash of colour with this cobalt top by Damsel in a Dress full details

what to wear on a date over 50 cobalt top image



A plain top with a twist from Jigsaw full details

plain shirt over 50 image



A bardot top  by Karen Millen full details

bardot top for dates over 50 image


Daytime dress – fresh and flattering from Boden full details

daytime dress for dating over 50 from Boden



For evenings I liked this studded dress from Damsel in a Dress – and it has sleeves 🙂 full details 

red dress to wear on a date over 50


For more ‘red’ inspiration , we pulled together a fabulous red collection in our Valentine’s style feature

Fun leather biker jacket in pink like this one from Barbour full details

pink leather biker jacket image


……or a black jacket  like this one by Reiss full details

black leather biker jacket image


This carvela studded court shoe has kitten heels –  a good heel height for most outfits and occasions.full details

studded kitten heel court show image



You don’t need to go out and buy a whole new wardrobe, pull together the clothes you feel most confident in. You want what you wear to reflect your personality. Remember the 3 ‘f’ s of dating. Fun, Familiar and Free. Shop in your own wardrobe first!

If you want to give yourself that extra confidence boost invest in a new lipstick – or book yourself in for a mini-makeover at a makeup counter at a  department store .  You want to be the best confident version of you.

If you are a little unsure about what to wear , then ask a friend who knows you well, and whose opinion you trust to see what you are planning to wear.

If you are feeling apprehensive and think  you might find it difficult to find things to talk about on your date, then wear a piece of statement jewellery that has a story attached to it that you can use as a conversation piece.


Ceri Wheeldon

Ceri is Founder and Editor of Fabafterfifty.co.uk She is a frequent speaker at events and in the media on topics related to women over 50 , including style and living agelessly. With 20+ years experience as a headhunter Ceri also now helps support those looking to extend their working lives.

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