In the Bedroom in 2010, open the closet and then the two top drawers. You should notice underwear in both of them. Move all the underwear to one of the drawers.
Below is a full walkthrough of every missable achievement in the game with timestamps and English commentary!
Timestamps:
0:00 - Intro
0:17 - Solve A Puzzle Achievement (1997)
0:30 - Blast Some Tunes Achievement (1997)
1:00 - A Sometimes Food Achievement (2004)
1:35 - Electrical Hazard Achievement (2004)
1:58 - Strike A Pose Achievement (2004)
2:22 - Gotta Flush Em All Achievement 1/7 (2004)
2:32 - Game On Achievement (2007)
3:03 - Hat On Head Achievement (2007)
3:47 - Gotta Flush Em All Achievement 2/7 (2007)
3:53 - Tidy Whities Achievement (2010)4:45 - Brew Some Coffee Achievement (2010)
5:55 - Gotta Flush Em All Achievement 3/7 (2010)
6:01 - Rediscover Childhood Achievement (2012)
6:30 - Brilliantly Solved Achievement (2013)
7:20 - 12 : 00 Achievement (2013)
7:57 - Gotta Flush Em All Achievement 4/7 (2013)
8:04 - Gotta Flush Em All Achievement 5/7 (2015)
8:11 - Fuzzy Friends & Baby Builder Achievements (2018)
9:21 - Gotta Flush Em All Achievement 6 & 7/7 (2018)