September is such a weird month for getting dressed, right? It’s still warm, some days feel completely like summer and others go weirdly autumnal. And even though I know we still have a few more weeks of warm weather here in Spain, I’m really starting to crave autumn — but don’t tell anyone I said that!
What I do love about this time of year, though, is how much fun you can have mixing seasons. Linen with leather? Yep. Loafers and socks with shorts? Absolutely. Summer dresses with heavier jackets? Even better. It’s that little window where almost anything goes, and somehow the slightly unexpected combinations look extremely cool.
So this week I’ve prepared five easy outfit formulas for the in-between weather, which might give you some inspiration in what to wear right now.
Followed by a closer look at the first few days of my Isn’t That Yesterday’s Outfit? challenge — what I repeated, what worked, what absolutely didn’t, and whether going back to basics actually made getting dressed easier. This second part is for paid subscribers. If you want to come behind the scenes with me while I test this challenge properly, the good outfits, the bad ones, the things I’m learning and the bits I’d do differently, can I interest you in upgrading? Your support genuinely gives me more time to create this kind of content.
5 Outfits for This Weird In-Between Season
One of the nicest things about transitional weather is that you don’t have to suddenly pack away all the summer pieces you still love wearing. Instead, you can slowly start introducing richer colours, different textures and a few more autumnal pieces, and make what you already own feel new again.
So here are five easy outfit formulas for that awkward in-between bit, when you want to start dressing for the new season without looking completely ridiculous because it’s still 25 degrees in the afternoon.
1. Summer dress + cardigan + leather jacket + loafers
This is basically summer underneath, autumn on top. A floaty printed dress still makes complete sense when it’s warm, but the cobalt cardigan, brown leather and loafers immediately make it feel less summery.
I especially like the socks with loafers here because they are such a small seasonal switch. And you can obviously take the leather jacket just in case the weather gets colder.
Why it works: you are not trying to make the dress look “autumnal”, you’re just changing what you wear it with. The raffia bag adds that little nod to summer and adds a whole lots of more texture to the outfit.
2. Mini dress + bomber jacket + ballet flats
One of the easiest ways to keep wearing a bright summer dress is to add a jacket that feels completely different from it and I love how a bomber jacket has the power to add edge to the most feminine piece.
The orange and olive combination is slightly unexpected, which is exactly why it works right now, and the burgundy ballet flats bring in an autumn richer tone without making the whole thing feel heavy.
Why it works: the summer silhouette stays, but the colours and jacket start moving the outfit into the next season.
3. Tank + sarong skirt + oversized blazer + ballet flats
This is exactly the kind of outfit I love for September because the base could easily be a summer outfit: tank + printed skirt.
Then you add the oversized blazer and suddenly it feels much more polished and transitional. The white ballet flats and woven bag stop it from going too autumnal.
Why it works: a structured layer gives lightweight summer pieces more weight.
4. White T-shirt + wide-leg trousers + colourful knit + summer shoes
Probably the easiest formula to recreate right now.
Start with a completely basic base like a white tee + relaxed trousers, add a colourful knit around your waist. Wear it properly if it gets cooler, always showing a little bit of the white t-shirt underneath for contrast.
And I’d still wear the flip-flops. We are transitioning, not forgetting it’s still technically summer.
Why it works: you have an autumn layer ready, but the outfit still makes sense if it’s 26 degrees outside.
5. Summer dress + leather jacket + closed-toe mules
Possibly my favourite way to extend the life of linen summer dresses.
The pale pink dress is very summery on its own, but that gorgeous burgundy leather jacket adds a completely different point of interest, suede mules and a darker woven bag completely change the mood. I love that contrast between something soft and feminine and something heavier and slightly tougher.
Why it works: instead of changing the main piece, you change the texture and mood around it with things you already probably have in your wardrobe: leather, suede and deeper hues instantly make the same dress feel more autumn.
A Week in Outfits: Back to Basics
I have a fashion theory: when you are feeling a bit bored of your wardrobe, overwhelmed by choice and have absolutely no idea where to start, one of the best things you can do is go back to your basics.
The pieces that feel easy. Natural. Your comfort outfits. The things you reach for when everything else fails. These are basically your core pieces — the ones that give your wardrobe some structure. Maybe it’s your jeans, your midi skirts, your statement trousers, your pull-on ones… the pieces that somehow make an outfit feel right, even when you haven’t really planned it.
