Getting dressed between seasons is about layering intelligently rather than committing too early to knitwear and heavy coats. Service Works and Pexwear's lighter jackets do a lot of the work here. Cut from tough cotton twill with that rugged, workwear feel, they're substantial enough for a cooler evening without tipping into full autumn armour.
For when the temperature actually drops, Universal Works' Wool Zip Waistcoat is the smart addition: a recycled wool blend that's light but properly insulating, the kind of piece you can throw on over a tee without overthinking it. And while full knitwear season might be a few weeks off yet, Howlin's Birth of the Cool knits come in a range of bold colourways and have been constructed from lightweight 100% Scottish wool. These are worth having in your rotation early.
If there's one genuinely essential transitional item, it's the overshirt. Stone Island's Mineral Dyed versions have a relaxed, faded handle thanks to the unusual dyeing process. Another Aspect's Another Overshirt brings real weight and a textured check that holds its own, while You Must Create's PJ Overshirt has a soft brushed handle for something softer against the skin.
Sitting alongside them is the NN07 Gael Jacket, a Peggs & son mainstay in its own right, and the piece Jeremy Allen White made unavoidable in The Bear. Here the check pattern, proportions, and structure make it as versatile as it is wearable.
Footwear needs the same flexible thinking. Tarvas's Easy Hiker, made in Helsinki, is built for the actual reality of autumn: long, muddy walks where grip and weather resistance matters. The same can be said for the Jasper Zionic from Keen. At the other end, visvim's Fabro is the treat option: a handmade, luxe take on the penny loafer in two colourways that are genuinely easy to wear, not just easy to admire. Between the three, you've got the season covered from the practical to the indulgent.
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