Your Guide to Transitional Season Style
Sharing my top tips for nailing transitional looks, plus a breakdown of some of my favourite outfits for the in-between seasons!
I was asked over on Instagram the other day how I manage to pull off wearing sandals with autumn/winter outfits without it looking odd—and it got me thinking about transitional dressing.
This time of year is probably one of my favourite seasons to dress for, but I realised I’ve never really broken down how I put these outfits together. I just love the freedom of mixing pieces from my summer wardrobe with cooler layers. That said, transitional dressing can be tricky to get right. One day it’s crisp and cool, the next it hits 27°C by midday—and suddenly the outfit that felt perfect at 8am feels completely wrong by lunchtime.
Tricks to nailing transitional dressing
Over the years, I’ve learned a few tricks to make this in-between weather feel less unpredictable and more like an opportunity to experiment and stretch your wardrobe a little further. Here’s what works for me when dressing between seasons:
1. Layers Are Everything
Not groundbreaking, I know—but the right layers make all the difference. I lean into lightweight jackets (my Sezane Will jacket is a hero), tees, and breathable knits. Think items you can easily peel off or throw over your shoulders without fuss. Bonus points if they work tied around your waist or draped over your bag without ruining the look.
2. Keep Summer + Autumn Pieces in Rotation Together
I don’t do a big seasonal switchover. Instead, I gradually bring in the next season—so linen pants might still be in rotation, now paired with a cotton knit instead of a tank. A dress I wore with sandals last month might get a new life with boots and a cardigan. This slow shift helps keep things feeling fresh and more versatile.
3. Footwear Makes the Outfit Feel ‘Right’
Shoes carry so much seasonal weight. In early autumn or late spring, switching your shoes can totally transform a look. I’ll often start the day in sandals and end in loafers or sneakers. An outfit that feels too summery? Add boots. Too wintry? A canvas sneaker or a sandal works wonders.
4. Choose a Colour Story
I find it helps to work within a looser seasonal palette—soft browns, greens, creams, and black always feel like a good bridge between summer and autumn for me. It gives cohesion to outfits when the weather feels anything but.
Breaking down my transitional outfits
Breaking down 5 of my favourite transitional outfits and why I think they worked…
1. Tee + Jeans + Sweater + Sandals
Jeans and a tee will always be a favorite, but adding a sweater over the shoulders is an easy way to nod to cooler days.
2. Sweater + Ecru Jeans + Converse + Summer Tote Bag
These ecru jeans have become one of my favorite transitional pieces — I’ve actually worn them more outside of summer! Paired with a thicker-weight sweater, they perfectly balance the lighter bottom half.
3. Summer dress + Sandals
Dresses aren’t usually my go-to in the transitional season, but long sleeves, autumnal colours, or layering a sweater over the top make them a perfect alternative to pants
4. Silk pants + Sweater + Sneakers
I never thought these silk pants would become such a go-to for the transitional season, but teamed with darker, cosier pieces, they work for so many occasions!
5. White maxi skirt + Sleeveless Knit + Sandals
I loved wearing a white maxi skirt through summer, and I didn’t expect to get just as much wear out of it on cooler days too! Paired with a knit or a crewneck sweater, it’s an outfit formula that feels both elevated and effortless.
I hope this Substack has given you the confidence to build outfits for the in-between seasons that not only look effortless but are practical too for unpredictable weather! Feel free to share it with a friend who might also need a little inspiration at this time of year.
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Jumper and sandal outfits are 👌 I love to incorporate summer pieces in the cooler months!