Sadly - and we can't believe we're writing this - summer is coming to an end.
Yep, it's official, we're crawling our way to the chillier months. And all this season change means one thing: how can we get more wear out of our fave summer clothes. Your secret weapon? Transitional shoes.
What's a transitional shoe, you ask? Well, it's a shoe that can take you from season to season, normally consisting of closed-toe styles that thrive during the moments of in-betweenness that define the autumn, or spring months where the weather is changing and you don't quite know which way is up.
So, below, we run through the best transitional shoes to wear with your trusty summer skirts, taking them from bare leg season all the way to autumn.
Skirts and trainers
Personally, I'm a major fan of skirts and trainers as it's just such a versatile look with honestly so many variations. Keep it current with a pair of low profile trainers (skinny sole) or the Puma speedcat ballerina (a trainer x ballet pump hybrid) styled with a shorter skirt. Later into autumn, you might want to go for a knee-length silky slip and the aforementioned low profile trainer, which works well for flirty daytime dates or even work (if you have a relaxed dresscode).
If you're a Sambas girly, these go sooo well with a white midi skirt - you know the type, the tiered or prairie styles which have been everywhere this summer - or the low-slung khaki midi skirts which have also been enjoying their moment in the sun. If you're looking to get more wear out of a tennis skirt, or more structured minis, these styles go well with a chunkier shoe like the New Balance 505s. And finally, Gazelles go well with a more minimal, clean girl-esque styling, so minis or slinky midis are all good options here.
Everyone's clicking on...
Skirt and loafers
Loafers were basically born to go with a pleated skirt - be it a kilt or a tennis skirt - and to be styled with a preppy shirt. Like, it just makes sense. However, the pleated skirt can also come in longer, more autumn-appropriate styles which hit just above the knee or come in the shape of structured midis. These variations work just as well with a loafer and, once styled with socks, can keep you going well into September as a fun day wear look that works for a lunch plan or even work.
Skirt and ankle boots
Boots are an obvious transitional shoe, but it's worth noting that certain styles can be tricky to wear during changing weather. This includes styles like sheepskin boots or knee-high/over-the-knee boots which are just too hot to wear in August or September.
Ankle boots, especially of the chunky variety, are a good transitional shoe option and are easily paired with a shorter skirt. The chunkier the shoe, the more you can play with the silhouette and proportion of the skirt - I'm a big proponent of resurrecting your bubble skirts to pair with a statement ankle boot. This is, in particular, a fun look to wear to a bar or party as it's a bit unexpected and flirty.
Skirt and calf boots
Calf boots, like calf-length motorcycle boots, have been cropping up throughout late summer where they've been worn with long, flowy midi and maxi skirt styles. Obvi in an homage to the halcyon days of boho chic, this combo is one of the major trends set to dominate early autumn 2025 for casual dressing.
I'd say you can also style more structured calf boots (I'm thinking a more sleek leather, polished option) with a midi denim skirt, or a midi pencil skirt, but the key would be to pick skirt styles which feature a slit for breathability and to prevent the outfit from looking too stiff. This last option is also a pretty smart look for the office and can be dressed up or down.
Skirt and clogs
Clogs work well as a transeasonal shoe and can be styled with longer skirts, like a structured A-line skirt or a boho midi/maxi skirt, as well as shorter styles, like a mini or knee-length slip. What I would say is, you might want to whip out the socks on this one, and I'll tell you why.
I'm going to die on this hill: put a pair of socks on, and you can squeeze more life out of at least 50% of the big shoe styles that were trending this summer. This includes Mary Janes, jazz shoes, kitten heels and, yes, clogs. (Just don't try socks + thong sandals or flip-flops)
Specifically, I'm seeing plenty of sheer knee-high socks as well as white cotton statement socks keeping fashionistas' feet warm and dressing up these shoes for the colder months.
So, there you have it!
Megan Wallace (they/them) is Cosmopolitan UKβs Former Sex and Relationships Editor covering sexual pleasure, sex toys, LGBTQIA+ identity, dating and romance. They have covered sexuality and relationships for over five years and are the founder of the PULP zine, which publishes essays on culture and sex. In their spare time, they can be found exploring the London kink scene and planning dates on Feeld.
