The slip on shoe in its various forms is one of those practical solutions that works better as a style choice than most people expect. There’s a cleanliness to the silhouette that comes from the absence of lacing and that cleanliness works well with simple outfits where you want the footwear to feel effortless rather than considered. We love a clean leather slip on in a driving shoe or penny loafer adjacent style for weekend and casual situations where the ease of just sliding a shoe on without any lacing ceremony is genuinely appealing. Keep the rest of the outfit fairly streamlined and the slip on adds that effortless quality very effectively. The main thing to avoid is anything too casual in construction worn with an outfit that reads as smarter because the mismatch between the relaxed footwear and the more intentional outfit creates a disconnect that undermines both.