My Friends Helped Me Virtually Clean Out My Closet, and Man Was It Productive

I wore this dress last Spring and thought it was great in the moment. It's very feminine and frilly in a lightweight linen material, but I just haven't reached for it again.

Dana says: "That's really cute. Why do you want to throw that away? I would say keep, but wear it as a bathing suit cover-up. I see this dress in high Summer with a T-strap sandal and one of those cute basket bags you have."

Laura says: "You can even wear it over shorts!"

Hannah says: "Since the belt is detachable, you can swap it out for a leather or a rope belt — something that grounds it a little bit more and makes it look less robe-y."

I've worn these jeans once. I got them when tie-dye was really taking off, and now they sit in the back of my closet. I feel like I'm never going to wear them again.

Dana says: "Where the fade to white and yellow starts is very strange placement for your legs, even though they're flattering on the top half. Maybe you can cut that part off and make them into cutoffs?"

Hannah says: "They're really cute, but the context on these are helpful. If you aren't wearing them, then toss 'em."

This was one of my first vintage purchases when I moved to New York for college and started thrifting from Beacon's Closet. I was thinking there might be a way to use the belt, but I feel like I'm over the dress. Yes, there's a nostalgia to it because it marks a certain time in my life, but I have other vintage dresses that I bought at the same time.

Laura says: "I feel like it flatters you perfectly, but it just does not feel like you."

Hannah says: "I like the idea of keeping the belt as a way to preserve this nostalgic moment for yourself."

Dana says: "You look beautiful in it, but I don't see you ever wearing this again. I wouldn't even keep the belt, I would donate as is and maybe someone else will find it and fall in love with it."

I bought this pleated set to wear to a wedding and ended up going with something else. This still sits in my closet with the tags on — I feel horrible when that happens.

Dana says: "I say toss. I love the colour on you and I think you should buy something else in yellow. I always feel like investment purchases are sometimes even harder to get rid of, but if something is from a store like Zara and you didn't exactly splurge, I think it's OK to get rid of."

Hannah says: "I think this is a good lesson in experimenting, but it's also about knowing your body's proportions. I've done this countless times where I see something I love at Zara for $30 and it sits in my closet the same way with the tags on because at the end of the day I can't transform my body to work for that trend or the cut is just wrong. When you're working with trend pieces, ask yourself what it is that's really working for you. If it's the silhouette, maybe gravitate towards a different peplum style."

Laura says: "I see through your tricks, and I feel like the hem is so cute when you're lifting your arms up, but it doesn't actually fit you that way. In which case I say toss. The body is just too long for you."

I own two pairs of white jeans, and these are my least favourite. They're cropped so I can show off my shoes, but I just don't feel like the cut is very now. I always reach for my other white jeans, so why am I hanging onto these?

Laura says: These aren't super current, but I feel like they're always in style. I think they fit you really well. I can't decide!

Dana says: I'm going to say toss. I think white jeans are stressful enough. If you personally put them on and don't like the way you look — maybe it's something about the fit or you just don't feel good when you wear them — then I don't like to hold onto stuff like that. It takes up space in your closet.

Hannah says: These highlight your tiny waist and they have a nice crop length that does work with a lot of shoes — especially with an easy sandal for Summer.