Hi Sarah, thank you for your review of our Dylan derbies. We're glad to hear that you love the nostalgic old school vibes it gives. Please give them around 4-5 wears for breaking in, and they'll become even more comfortable to wear! We recommend wearing thick, comfy socks to help with any discomfort in the achilles area for the first few times of wearing them. We hope you continue to enjoy your purchase. Thank you for choosing Rob & Mara!