Between Seasons: The shoes to wear right now

September marks the start of something new. Summer isn’t quite over, autumn hasn’t fully arrived, and getting dressed becomes all about finding the perfect balance between the two.

Too warm for heavy winter shoes, but ready to give your sandals a break? This is where transitional shoes come in. Think timeless loafers, refined moccasins, feminine ballerinas and effortless derbies — styles that feel right for now and will carry you seamlessly into the new season.

Discover the CTWLK shoes we’re wearing on repeat this September.

What shoes should you wear in September?

September calls for shoes that work with unpredictable weather and an in-between wardrobe. You want something more substantial than a summer sandal, without reaching for your winter boots just yet.

The answer? Loafers, moccasins, ballerinas and derbies.

These transitional shoe styles work just as well with lightweight trousers and dresses on warmer September days as they do with denim, tailoring and knitwear when temperatures start to drop.

1. Loafers & moccasins: the ultimate September staple

If there is one shoe that defines transitional dressing, it has to be the loafer.

Easy to wear, timeless and endlessly versatile, women’s loafers and moccasins are the perfect bridge between summer and autumn. Wear them with straight-leg jeans and a simple shirt for an effortless everyday look, or pair them with tailored trousers and an oversized blazer when you want something more polished.

For a classic September look, opt for warm, natural shades and tactile materials such as suede.

Our Patsy moccasins are a perfect example. Crafted in suede and available in different variations, their timeless silhouette makes them an easy choice for everyday dressing. The cognac Patsy/A6 in particular brings just the right amount of autumn into your wardrobe without feeling too heavy.

2. Derbies are back

Another style making its way back into our everyday rotation? Women’s derbies.

Borrowed from classic menswear but reinterpreted with a feminine approach, derbies instantly give an outfit a more structured feel. They’re also surprisingly easy to style.

Wear them with relaxed denim and a white T-shirt while the weather is still mild, then add socks, knitwear and a trench coat as autumn arrives.

The Giraf is one of our favourite transitional styles. Crafted in soft suede with clean lines and a relaxed character, it combines the polished look of a derby with the ease you want from an everyday shoe.

Discover CTWLK derbies →

3. Ballerinas aren’t going anywhere

Not ready to say goodbye to lighter shoes? You don’t have to.

Ballerinas are ideal for those warmer September days when boots still feel a little premature. Their lightweight silhouette works beautifully with denim, skirts, dresses and tailored trousers, making them one of the easiest shoes to transition from summer into autumn.

Go timeless and minimal, or use your shoes to add texture and personality to a simple outfit.

The Romah ballerina does exactly that. Its pointed silhouette and distinctive finish turn an everyday flat into something more expressive, while styles such as the Rally offer a softer, more understated take on the ballerina.

Explore CTWLK ballerinas →

4. Start introducing autumn colours

Transitioning into autumn doesn’t mean changing your entire wardrobe overnight.

One of the easiest ways to make your outfits feel more seasonal is simply to change your colour palette.

Swap bright summer shades for cognac, brown, beige, black and deeper neutrals. A suede loafer in cognac, for example, instantly makes white denim or a lightweight dress feel more September-appropriate.

The same goes for materials. Suede, leather and textured finishes add depth to an outfit while still being wearable on milder days.

How to style transitional shoes

The secret to September dressing is mixing pieces from both seasons.

Try pairing loafers with jeans, a T-shirt and a blazer. Style ballerinas with a midi skirt and lightweight knit. Combine derbies with tailored trousers and an oversized shirt, or wear suede moccasins with denim and a trench.

You don’t need a completely new wardrobe for autumn. Sometimes, changing your shoes is enough to shift the entire look.

Step into September with CTWLK

September is the month of transition — and your shoes are the perfect place to start.

From women’s loafers and moccasins to ballerinas and derbies, CTWLK offers timeless styles designed to move effortlessly between seasons.

Wear them now with the last pieces of your summer wardrobe, and style them differently as the days slowly become cooler.

Because a new season doesn’t have to start all at once.

Discover the CTWLK women’s collection and find your perfect pair for September.