What To Wear On A Date When You're Over 60

pink and green _ Style At A Certain Age
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Evergreen stylish trends that are both comfortable and guaranteed to make you look elegant for that hot date. These are my suggestions that’ll give you flatteringly youthful looks to moderately formal ones.

So you’ve secured a date? 

Congratulations on making it this far. 

Now let’s dress you up. No, your regular every day looks just won’t cut it this time. For this date, you’re going to show up looking like a dish! This article will help you avoid “old-fashioned” like the plague then settle for “classic” but with a dash of caution.

Flattering Skirts for Comfort and Style

If you must wear a skirt then pick a calf-length one, pair it with comfy tennis shoes for a fresh look. 

Credit: Style At A Certain Age

A white classic blouse is always timeless. 

Toss one for a tucked-in t-shirt for a much youthful look. If you’re a heels kind of lady then strut on!

Going On A Date in the Cold of Winter?

Winter dates? 

Credit: Outfittrends.com

I’m going to let you in on a secret; use layers for warmth, comfort, and sophistication. 

Ponchos, jeans, scarves, and long boots are all you’ll need. 

Credit Pouted.com

The trick is in the colours and how you decide to mix them with different fabric textures. These ideas also blend pretty well in the Fall season too. Our most comfy but trendy date outfits yet!



  • Don’t forget to throw in the accessories to give the outfit a “special occasion” feel.
  •  Feel free to pick your colours that complement your features better. 
  • Get a good fit for the denim jeans so that the tight ones won’t feel like a death-grip. 
  • Try to also make sure that they aren’t overly long which only makes them look shabby and takes away the attention from your shape.

Simple Yet Elegant Dresses

Dresses work for just about every occasion. 

Picking the right one makes all the difference and I’m gushing over semi-formal maxi-dresses. These would be perfect for you for that hint of elegance and if you LOVE adding shine to your outfits.

If you wear your hair short then add a subtle but catchy neckpiece and complementary earrings.  A handbag that matches your boots is a great idea plus some shades to finish the look. 

Things to Avoid Wearing on a Date

Whilst we’re at it, here’s a list of items to absolutely avoid for that date :

  • Muumuus
  • Elastic waisted pants (especially if they are plain)
  • Embroidered fashion pieces
  • Jesus sandals
  • Dull oversized t-shirts

Are you ready to freshen up that dating wardrobe?

Dating when you’re over 60 can seem like quite the sport but it shouldn’t be. Remember to not worry about what other people are thinking about you as long as you’re comfortable. If you’ve found some clothing items on our list that can only be found in a store meant for younger people go for it! No. No one will judge you for it. 

Which outfit caught your fancy? We’d love to know the hits in the comments below. 

Planning a date? Here are 5 date night ideas that men over 60 will love.


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