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17 winter shoes for women in their 40s, 50s and 60s who want to look stylish (but still supported)


Chic shoes for older women who now want style AND comfort. Shop our top picks for women in their forties, fifties and sixties...


best shoes for women over forty, fifty, and sixty© Spotlight

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Leanne Bayley
Leanne BayleyDirector of Lifestyle & Commerce
Updated: October 27, 2025
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I know I'm the right person to write this article, because I understand how tough it is to find nice shoes that don't hurt your feet. As I get older (I'm in my forties) I notice that I can't reach for the high heels I used to wear in my twenties. I need support. I need some comfort. If it's a wide-fit design, I'm happier, and when there are half sizes available I'm in my element. After writing an article about the best occasion wear dresses for women over a certain age, I decided I wanted to help in the footwear department, too. I scoured the virtual aisles for some top picks and I've even looked towards the royals (my other specialist subject!) for some expert guidance as well.

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And talking of experts, there was one person I really wanted to reach out to when it comes to the royals, and that's Samantha, she's the woman behind the popular Royal Fashion Daily Instagram account (formerly known as Royal Fashion Police). She's a marvel at documenting royal outfits, so I was desperate to know what the 50+ royals can teach us about their shoe choices for a special event.

Queen Letizia, 53, is a big fan of the slingback pointy shoe© WireImage
Queen Letizia, 53, is a big fan of the slingback pointy shoe

Samantha notes that royals tend to reach for their low block heel shoes and their wedges. She said: "These both offer elegance with comfort, especially for long engagements. Both Queen Camilla and the Duchess of Edinburgh often choose them for practicality without sacrificing style."

My editor's pick

My editor's pick: These fabulous shoes from H&M - they have a low heel and they have an ankle strap© Leanne Bayley
My editor's pick: These fabulous shoes from H&M - they have a low heel and they have an ankle strap.

How I chose the best winter shoes for older women

  • Style AND comfort: I want this to be a stylish edit but I also want to make sure the shoes will be comfortable, too. From ankle straps to cushion support and wide fit options, I want to give you choice.
  • Cost: I've tried to choose winter sandals and shoes that you can wear time and time again so if they're a little more expensive, I'm hoping the investment will be worth it in the long run. I also looked at some of my favourite brands, and the ones that I trust. 
  • Age appropiate: As you know, this edit is all about shoes handpicked with an age category in mind. I've tried to pick a mix of styles - after all, just because you've reached a certain age, doesn't necessarily mean you have to change your style. I'm hoping you'll get the inspiration that works FOR YOU. 
Laura Dern, 58, shows off her va-va-voom style wearing a pair of glam red shoes© Getty Images
Laura Dern, 58, shows off her va-va-voom style wearing a pair of glam red shoes

Best winter shoes for women over 40, 50, and 60

Boden T-Bar Point Heels

Boden black heels© Boden

Why I love them:

  • Ankle support
  • Low heel
  • On trend design

Elegant and strappy, these T-bar heels - which are also available in red - are crafted from long-lasting leather with black mesh detail.

Style with: Jeans and a top or party dress.

H&M Bow Detail Heeled Shoes

H&M Bow Detail Heeled Shoes© H&M

Why I love them:

  • Stylish
  • Glam but still comfortable 
  • They have the wow factor

Everyone needs a pair of glam mini heels in their shoe cupboard - especially in the Christmas party months. These bow-detail shoes from H&M feature an adjustable strap that wraps around the ankle and a delightful velvet bow. 

Style with: Your party edit

Dune London 'Channel' Buckle-Detail Heeled Courts

Dune London 'Channel' Buckle-Detail Heeled Courts© Dune London

Why I love them:

  • Stylish
  • Supportive ankle strap
  • Available in pink and blue as well

You just have to take a look at the Zara new-in section to see glitzy shoes are everywhere. But boy do they look uncomfortable. What I love about this pair is that these sandals have the glitz but they also have the ankle support.

Style with: A glam outfit for a special party.

Sole Bliss 'Prestige' Black Satin Shoes

Sole Bliss 'Prestige' Black Satin Shoes© Sole Bliss

Why I love them:

  • Stylish
  • Deep toe box
  • Ultra-cushioned footbed 
  • Anti-pronating arch support

Sole Bliss is a brand that older women tend to gravitate to (Helen Mirren and Queen Camilla are both fans!) as they are ideal for anyone who suffers with bunions or fallen arches. These have a cushioning stretch panel for bunions, and not one, not two, but three layers of cushioning under foot.

Style with: Jeans and party wear.

River Island Black Satin Bow Pointed Toe Shoes

River Island Black Satin Bow Pointed Toe Shoes© River Island

Why I love them:

  • Stylish
  • Flat if you don't like stilettos
  • Catwalk inspired

River Island is a great place to find nice shoes if you ask me. I saw plenty of stylish options available, but I chose these bow flat shoes because they're a great all-rounder. 

Style with: Trousers like the model, or a midi dress for dance floor friendly occasion shoes.

Next Black Forever Comfort Jewel Trim Pointed Court Heels

Next Black Forever Comfort Jewel Trim Pointed Court Heels© Next

Why I love them:

  • Stylish 
  • Forever Comfort padding
  • Perfect for party season

Next is one of my top choices when it comes to evening shoes, mainly because of the padded footbed. 

Emmy London 'Josie' Black Tweed Low Block Heel

Emmy London 'Josie' Black Tweed Low Block Heel© Emmy London

Why I love them:

  • Stylish 
  • Available in 23 colours
  • Available in a stiletto shape, also. 

Ok, so I've included these because they are royal approved (Princess Kate's a major fan) but also because they're gorgeous and comfort is top priority. Crafted from Italian black tweed, the comfortable block heel is the right height for lengthening your legs while remaining comfortable to wear all day. The shoe features understated gold shimmer, adding depth and interest to any look

Style with: Evening wear, especially good for a mother of the bride outfit or a wedding guest outfit. 

ASOS Skip Slingback Kitten Heel Burgundy Shoes

ASOS Skip Slingback Kitten Heel Burgundy Shoes© ASOS

Why I love them:

  • Stylish 
  • Slingback design
  • Colour of the season

Kitten heel shoes aren't for everyone, but if you're a fan, you'll love these sequin dpointy shoes from ASOS. You can't deny they've been the ultimate 'trendy' colour of 2025.

Style with: Leather trousers, dresses, wide-leg trousers, wide-leg jeans.

Monsoon Bow Block Heel Sandals In Gold

Monsoon Bow Block Heel Sandals In Gold© Monsoon

Why I love them:

  • Stylish 
  • Chunky heel (good for walking on uneven surfaces) 
  • Secure ankle strap 
  • Will go with lots in your wardrobe

If you're after some party shoes, these are the ones. Aren't they just so pretty? They're the dazzling lift your feet need. Designed with a chunky platform heel and open toe topped with a metallic sheen, these sandals are primed for wedding guest season. 

Style with: Your occasion wear dress, jumpsuit or suit.

FitFlop 'Delicato' Metallic Mary Jane Shoes

FitFlop 'Delicato' Metallic Mary Jane Shoes© FitFlop

Why I love them:

  • Easy to wear
  • Comfort factors
  • Different colour options
  • Some half sizes available 

You might think of Fitflop for your summer shoe of choice, but these Mary Jane shoes are ideal if you want a glam pair of shoes that feel like a sneaker. 

They are ergonomically engineered to help optimise your body's alignment, and there's Dynamicush' cushioning hidden in the rubber outsole. 

Style with: A pair of jeans and your Christmas jumper. 

M&S Collection Gem Studded Flat Ballet Pumps

M&S Collection Gem Studded Flat Ballet Pumps© M&S

Why I love them:

  • Flat 
  • Slip-on design  
  • On trend
  • Easy to wear

If you prefer a flat shoe over a pair of heels, but struggle to find something that's wow worthy enough, this pair from M&S is spot-on. 

Style with: Jeans and a trophy jacket.

Kurt Geiger Belgravia Bow Heel Slingback Shoes

Kurt Geiger Belgravia Bow Heel Slingback Shoes© Kurt Geiger

Why I love them:

  • Stylish
  • Padded footbed
  • A low heel

Kurt Geiger is a major player when it comes to party wear, and the large crystal bow will have you desperate to get on the dance floor. 

Style with: Your party wear.

Mint Velvet 'Gigi' Silver Leather Loafers

Mint Velvet 'Gigi' Silver Leather Loafers© Mint Velvet

Why I love them:

  • Stylish
  • Flat
  • A comfortable round toe

Mint Velvet is a firm favourite with the fashion crowd and lots of the styles tend to sell out fast. I love these silver metallic loafers for an alternative to a party shoe - I think they'll really amp up a look. 

Style with: A pair of black trousers or jeans.

Gabor 'Jiffy' Ballerina Flat Shoes

Gabor 'Jiffy' Ballerina Flat Shoes© Gabor

Why I love them:

  • Stylish 
  • Slip pn
  • Good reviews

The Gabor Jiffy ballerina flats are guaranteed to make any outfit that extra bit sophisticated. The ballerina silhouette has a 1.5cm heel, meaning they are the perfect flat, while remaining stunning at every step. Finished with the Jiffy’s buckle fastening, which enhances the shoes charm and manmade sole for support. 

Style with: Jeans, skirts and dresses. 

Russell & Bromley Silver Hillcliffe Court Mid Shoes

Russell & Bromley Silver Hillcliffe Court Mid Shoes© Russell & Bromley

Why I love them:

  • Stylish
  • Low heel
  • Comfy & easy to wear

Russell & Bromley is a great option for footwear. This brand makes beautiful leather shoes, and they’re renowned for being stylish and super comfortable.

These are the kind of shoes that really do last forever.

Style with: Your winter party dresses or jeans

Mango Kitten Heel Pom Pom Shoes

Mango Kitten Heel Pom Pom Shoes© Mango

Why I love them:

  • Stylish
  • Ankle strap
  • Fun pom pom detailing

Mango is smashing it out of the park for winter 2025, there are some gorgeous shoes on site at the moment. I decided to share this pair because I think they're great for a occasion wear as they go with everything.

Style with: Glam outfits this Christmas

Clarks 'Sensa 15 Trim' Ballet Flat Slingback Shoes

Clarks 'Sensa 15 Trim' Ballet Flat Slingback Shoes© Clarks

Why I love them:

  • Stylish
  • Lightweight
  • Timeless design

These slingback shoes from Clarks could be designer if you squinted, but I guarantee they'd be comfier than a pricey pair. Crafted from butter-soft leather, this elegant shoe is elevated by a sleek buckle. Comfort a top priority? These feature a moulded Contour Cushion footbed. 

Style with: Jeans and a blouse or a dress.

What to look for when it comes to comfortable shoes - 5 top tips

Shopping for shoes changes when comfort is a priority, but that doesn't mean you can't look chic as well. Here are some things you need to pay attention to.

  1. Cushioned insoles: If you can find somes that have a padded footbed you're in luck. These definitely help with comfort. If you can't, you might want to order some insoles from Amazon to help. 
  2. Breathable materials: These help keep your feet cool and dry, keeping blisters at bay. 
  3. Roomy toe-box: If you suffer with any sort of neuroma to the foot, or a bunion, you need to ensure that you've got a roomy toe-box area. Pointy shoes may well be lovely to look at but if you struggle with a bunion, they might not be for you. 
  4. Durable soles: We don't want you slipping all over the place. Look for shoes that might have a textured sole or good traction. In the past I've gently scored the bottom of my shoes with a knife in a criss-cross pattern. Did it help? A little. 
  5. Heel height: I haven't featured any shoes in this edit that are high, but if you do, look out for block heels, wedges or platforms for better support.
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