Baggy jeans with sneakers is by far my easiest, casual winter outfit. The best sneakers with baggy jeans are sleek, low-profile sneakers, rather than chunky, Dad-like sneakers. You want sneakers that almost have a ballet flat vibe – these are the kind that let the baggy jean hems breathe and offer the right kind of balance. Because it’s winter, I strongly prefer sneakers that are suede, in deeper jewel tones. The extra texture and rich color seems to hold their own better against thick, cozy knits and warm jackets.