Boots with skirts and dresses after 60: my styling notes

I’ve recently bought a new pair of black knee-high boots that I will wear on cold, but dry, days throughout the rest of the winter and into Spring. I know boots always look good under trousers and jeans but I am keen to wear boots under dresses and skirts too.

Here I am styling my leather boots with skirts and a dress that I have with me – I travel south in the winters and only pack a small capsule wardrobe to see me through till Springtime. I want the boots to add a more structured look to each outfit. And I want the boots to look good with a coat or jacket. And without.

Short video of my try-on

These boots are Marks and Spencer’s black leather riding boots with a traditional low flat heel and a rounded toe. At 76 my days of heels, even kitten heels, are over! Riding boots offer room for my wide feet and ankles too. They rise to just under my knee which gives a long narrow black rectangle from skirt hem to floor. This heavier look works well in colder weather with thick clothes – but here I want to style my boots with lightweight skirts and dresses.

Styling boots with a linen midi dress

I’m wearing boots with a linen dress. I want to be sure that this combination looks good with my raincoat and tote bag when I’m out shopping. But looks just as good if I stop off at a friend’s house for coffee on my way home.

It has become the style today to extend the life of lightweight summer skirts and dresses through colder days, usually by adding a sweater and boots or sneakers. This is such an easy to wear dress that I feel great in it with these boots.

Wearing boots with a denim skirt

The weight of a denim skirt works well with the heavier look of high boots. I like the balanced proportions in this outfit above. The silhouette is divided into four similar lengths: boot heel to skirt hem, skirt hem to jacket hem, jacket hem to collar, and collar to top of head.

Boots and denim hint at a more outdoor rugged lifestyle – cowgirl on a ranch perhaps hahaha! For this outfit I decided to leave the horse at home and take a stroll into town. So as not too look too wintery on a windy but fine day, I’ve chosen boots with a sleeveless puffer jacket over a Brora silk shirt.

Once inside, I think the outfit without the bag and jacket still looks in proportion and not too heavy, despite the black boots.

Styling riding boots with a gathered cotton summer skirt

When I bought these boots in black I was thinking of this black poplin skirt I bought in the summer. Would the boots go with a full cotton skirt. I wondered. So this look brings together my heaviest most wintery coat with the poplin unlined skirt. I think the long column of black, from the boots through the skirt to a little second-hand top, helps the outfit to look chic. Building on this column of black I reckon I can wear almost any jacket, cardigan or coat on top.

I especially like this style with my pale raincoat. It’s very relaxing to wear and both the shoulder bag and the dark brown tote look fine with it. I could wear a different colored top but I don’t think the outfit would look quite as good.

Once again, I need to see what the outfit with top, skirt and boots will look like indoors, without a coat. I am happy with this all-black style and feel it gives me the option to wear the summer skirt through winter and Spring.

I’ve researched the best boots for women over 50 (or so) and you can read my list of favorites in this post: Best Boots 2026 for Women Over 50

If you enjoy reading about style for women after 60 you might like these posts next:

How to Style Leggings to Look Great

How I’m Styling a Summer Shirtdress