By transitional footwear I mean shoes that you can wear in mild weather that’s not too hot or cold. Breezier than booties but more insulated than sandals. 

• Kate Spade New York ‘Gwen’ Flat: I have this pointy toe flat on my radar in either silver or gold because the silhouette is ladylike and modern. I love the way it looks with skirts, frocks and tapered jeans or trousers. Warning: it does make your feet look long, and the toe box, although regular width, will pinch if you prefer a roomy fit. I find that the pinch of pointy toes sometimes goes away with wear, but your mileage may vary. Also available in red and black. 
• Attilio Giusti Leombruni Pinked Loafer: It’s rare to see a shoe in an air force blue. So fab! The best part about the shoe is that the heel isn’t quite flat. 
• Joe’s ‘Dakota’ Flat: More sci-fi fabness. Size up at least half a size. 
• Cole Haan ‘Monroe Reflective’ Loafer: Extremely comfy and a true updated classic. Comes in fun colours and a cool reflective silver. 
• Anyi Lu Sophia Pump: Anyi Lu keeps repeating this style because it’s a winner. Particularly versatile as a textured neutral. 
• Indigo by Clarks Purity Snow Pump: This one is for high heeled wedge fans. Casual, textured, patterned and neutral. 

Most of these shoes are “slip-on” styles, some with low vamps and some with higher vamps. If you have trouble with ballet flats or pumps staying on your feet, try slip-on shoes with higher vamps. They provide better support and don’t slip off as you stride.