冬 天 (winter)， 能 (can) 穿 (wear) 多 少 (amount) 穿 (wear) 多 少 (amount)； 夏 天 (summer)，能 (can) 穿 (wear) 多 (more) 少 (little) 穿 (wear) 多 (more) 少 (little)。 Without the word "夏天 (summer)" or "冬天 (winter)", it is difficult to segment the phrase "能 穿多少穿多少".
we usually need utilize the non-local information for more accurate word segmentation.