Which brings us to 2026. Bootcut jeans, straight-leg jeans, baggy denim, ripped jeans and exaggerated cuffs are all firmly back in the conversation, but recreating a 90s outfit from head to toe isn’t really the point. The easiest way to make them feel current is with the shoes.
Pointed heels sharpen a bootcut, Mary Janes give straight-leg jeans a sweeter spin, kitten-heel boots dress up distressed denim and platforms were practically made to sit beneath a chunky cuff.
Consider this your guide to the 90s jeans worth revisiting – and exactly what to wear on your feet with them now.
90s jeans are back in style with heels, ankle boots, and sandals for autumn 2026
Bootcut jeans with pointed-toe heels
Bootcut jeans are one of those 90s silhouettes that never stray too far from fashion’s radar. Fitted through the thigh before gently flaring from the knee, they have just enough drama to make an outfit feel considered without veering into full bell-bottom territory.
While the decade often saw them styled with loafers and ankle boots, pointed-toe heels give the shape a sleeker update for 2026. Look for a hem that falls almost to the floor, allowing just the tip of the shoe to peek through, and add a fitted knit, crisp shirt or leather jacket on top.