1. Oxfords
A good classic oxford will be more valuable and wearable than any pair of heels you’ve ever owned. It’s grunge but classy and feminine but chunky; the perfect balance for fall footwear. An amazing androgynous staple that can be a classy shoe, or a casual one. An exaggerated toe modernizes it as does a distressed, colored wash.
2. Denim Button-Downs
This is such a versatile basic that you can wear year round. Wear it in a light chambray or a little thicker and play around with different washes. Style a vintage scarf in the pocket, and leave a couple of buttons undone to add some va-va-voom to the menswear basic.
3. Slouchy Harem Trousers
Harem pants are super versatile soft pants, and the drop crotch gives them an edgy look. Very comfortable, and a version of sweatpants that you can actually wear outside. Great for business, brunch, or a night out on the town, with strategic shoe choices. Try with a more fitted top, like a silk halter.
4. Beanie
Play around with colors and patterns. Lightweight ones in cashmere look a little more classed up, while a thicker and chunkier knit will look a little more street wear inspired. Try a fuzzier one if you have straight hair, or a thin ribbed one if you want to cuff it for a tighter fit.