I Tried 5 Levels of Thrifting

Did you know in the middle of 2026, a teenager thrifted this Lakers jacket for three bucks? Not significant, right? Well, it's sold for $90,000. And that is because it belonged to Wilt Chamberlain worn during his very last season. This is just one of the many stories that has made thrifting kind of a thing. And I've only been thrifting once as an adult. So that is why today I'm going through five levels of thrifting to see what it's all about. And as the levels increase, the more intense, intriguing, and epic this video will get. I'm overwhelmed right now. Our goals are number one, to buy an outfit from each level and two, enjoy the experience of thrifting. Level one, the garage sale. So I drove all the way to the burbs of Chicago and let's just say this weather was great. Yeah, but not really. And I had a feeling this was going to affect our garage sale choices, but surprisingly there was a couple of houses and then I found a gem. How much is this? $10. Yep. You heard that right. $10. It didn't feel right to me. So I just gave her the $40 in cash I had on me. Plus I do find it uncomfortable to film in other people's homes. Luckily she was cool. So the jacket was secured, but as luck would have it, no more garage sales. And this made me nervous because we have to complete an outfit for each level. So the next day I whipped out the iPad because luckily with the power of the internets, you can have your own garage sale online via Facebook marketplace. But let's spice it up a little bit. So I'm going to whip out the thrifting challenge board. Whatever we pick, we must do at each level. So since we're on the first level, feeling a little lucky, lucky number seven. How about we go with that? Let's see what we get. First item, my size. This is where the first item that I see that's my size on Facebook marketplace, we must buy. So what I stumbled across was this sweater right here from Ralph. Let's send a DM. A little nervous. My first time doing a Facebook marketplace buying. Anyone else feel like it's kind of awkward? I don't know. Maybe it's just me, but I was making my way downtown, driving fast. Also don't hit on the Hello Kitty. This is the wifey's car. Let's pick up that item. Oh, hi. Hi. Well, here you go. Thank you so much. Challenge item secured time for the pants. And after being ghosted by so many people, Kaylee, I'm looking at you. We ended up securing these corduroy pants and here's how the fit turned out. Wow. This is crazy. I'm not going to lie. This jacket was an insane find. We got really lucky and the outfit was only 80 bucks. Could have been 50 if I got the jacket for 10, but the overall experience was quite bumpy onto level two. Level two, we have Goodwill, one of the most popular secondhand stores. And you can definitely tell because with over 4,200 locations across the globe, Goodwill still operates as a nonprofit taking in donations and selling it back to the community to fund community-based programs like job placement and career training, which does reflect on the price tags and that has fundamentally changed the fashion industry as a whole, but more on that in a bit. Hopefully we can find some good stuff. This is a bigger space as well. Never been. We'll see what we can find. But first, thrifting war challenge. The Facebook marketplace was fun, but for Goodwill, you know, in Chinese culture, number eight or bot, that's good luck. I'm feeling number eight. Let's see what we get. Technical difficulties. We got stranger's choice. This is where we will have to ask a stranger to make a decision for us and whatever the choice is, we got to roll with. This, this will be fun. See what we can find. And as you walk into this West Loop location, you'll find a nice warehouse ambience, interesting wall art, some Italian brain rot toys for some reason, the furniture and sports gear section. And of course the clothes. Oh, there's, there's some good stuff here, guys. Two-tone caps, dude. This crew neck right here looks pretty nice. 529. Nice color to it. Yo, MCR, dude. What's your favorite track on a Black Parade? Black Parade? I like, um, This Is How I Disappear too. It's a good song. As you can see, there was a lot of options, good and bad, like these Toms, if y'all remember that and an open bag of chips. Okay. So with level two stores, you really got to dig to find some good items. But eventually I found some Carhartts, nice graphic tops, leather coats, a clean pair of I was feeling a little more colorful, so I found these turquoise pants. They are women's, but I found them in the men's section. Must've got misplaced, but they do have a unique shape to them. And guess what? It was five bucks, which is why my parents absolutely love shopping at this place. Although I got clowned for it as a kid, at least it's cool now, right? Now over the years, what used to be a community-based thing has now become a phenomenon, creating and fueling entire industries just within the fashion space. Online reselling, other levels of thrift stores, which we'll get into, and even live selling from an app like whatnot. And Goodwill, well, they're at the forefront where most resellers rely on them for inventory. And then I came across something interesting that I've never seen before in any Goodwills. What is this? Mystery bags. $7.49 for a bunch of random stuff. That's more mystery bags right here. Size medium, we got mystery in every bag. And it says men's collared long sleeve. And since these are mystery bags, I decided to grab another so that we can uncomfortably ask a stranger for their choice. Talking to strangers for the camera is always awkward, so let's just do it. Fair warning. I'm sorry. You're going to have to sit through this. You're definitely going to get secondhand embarrassment. Time to talk to some strangers. Excuse me. Do we get, do you mind if we can get an opinion from you guys? Just like a pick? Yeah. No, just a picture. Like, or it's not a picture, a pick between one of these. Okay. Yeah. Pick left or right? Left or right. What do you think it'll look? Right. Right. We're going to roll with this. Thank you so much. Appreciate it. I quickly left the area to the furniture and electronics section. And I found some really cool things like some dumbbells, interesting reeds, great movies. If you're Vietnamese, you'll find this funny. And some clubs to practice my putt. It says it's a men's collared long sleeve. This will probably act as our top layer. So we'll get an under layer and then maybe some accessories. Of course, I was curious to see what was in the bag, but we will unbox it in the studio after we get all of our pieces. So for our shirt that goes underneath the top from the mystery bag, I decided to go with this light colored shirts for that monochromatic look. Now all these items alone, not even 20 bucks. So then I found this yellow trucker cap, this black bag to accessorize the fits. Let's check out. We got our items, 32 bucks. Pretty solid if I do say so myself. Here is the fit. Oh man. Yeah. Super colorful right now, but we still have that mystery bag. Let's give it open. Let's give it a go. Okay. Whoa. So this bag came with five different button all of various colors and patterns like this one with a cute colorful button. And even this one from the gap, these are our choices. I'm going to go with this purple shirt and I'm not going to lie from the side perspective. It looks kind of good and quite colorful. I'm a little out of my comfort zone with, with all these colors, nice shapes, super affordable. This was fun. This is dope. But yeah, those prices still crazy to me. Let's move on to level three. All right guys, for level three, we are here at Wicker Park. This is actually my first time being here. I guess it's like sort of a mini fashion district. I didn't even know there was a Supreme back there and there's a bit of a line developing right now. I guess there's some sort of drop going on, but we aren't here for Supreme. We are here for level three, which is a curated thrift shop. These are secondhand stores that have a curated collection of items geared towards the fashion enthusiast. And that usually means it is a bit pricier, but you really don't have to do as much digging as we had to do in Goodwill. Every city has plenty of their own like L train vintage in Brooklyn and in my hometown of Albuquerque, Heck Yeah Vintage seems to be the spot. But out here in the Chi, Layers Chicago is a favorite. Now remember guys, we have our thrifting challenge board. Since we're at level three, I'm feeling number three. Let's see, see what we get man. A little nervous. Employees choice. This is where we have to ask an employee for their choice of what piece we will have to add to the outfit. So this could go well. It could, it could not. Let's head inside. Looks like they're closed. All right, guys, it's been 84 years. I think, I think they're open now. Hey, what's up, man? Johnny. Good to meet you, bro. My first time here. So give me, give me a tour of the places. Yeah. Come on. Let's go. Now this here is Kevin. One of the few owners that was cool enough to let us film without music so that we don't get copyrighted, which is just a few of the reasons why this is one of the best shops in the Then proceeded to give us a full rundown of the place. Man, that's so much. This place is huge. Got a little display case over here. Some of the little bit collectibles, even like a little middle console, more bags, more shoes. Okay. They had a nice warm entryway that was cozy, welcoming, clothing organized by category and by color. Got to love that attention to detail and general decor that the crew loves making this space feel nostalgic. Got to put some respect on the clones. This is how layers does it. You'll probably find something similar at your curated thrift shop in your city. And I did a ton of research on the secondhand market. I only have so much experience. So why not ask an owner of a thrift shop about his experience with thrifting and the scene in general? How'd you guys get into like curation and thrifting in general? I grew up just going to thrift stores all the time. It was affordable for us growing up. You got kind of like bullied for it. Like, Oh, why are you wearing secondhand clothes? Why are you wearing your big shirt? I'm like, Oh, like it's what I like. And then funny how nowadays it's cool now. Yeah. My sister in like junior high school, she would just take me to Unique and Salvation Army. And she'd just say like, I'm not buying you new clothes. You go find something over there. And I guess that's where like the thrill of the hunt started. Why do you think thrifting is so popular now? I think it's just more of a trend thing right now, but I really love it because it's making a lot of people eco-conscious. That's right. As the fashion industry is the second highest polluter and more specifically fast fashion. Now with the secondhand market on average, everybody wins. Resellers can make a living. Consumers can go out and touch some grass while also getting good pieces at a nice price. Some great insights from Kevin, but for now, I got a task, man. I got to ask one of you guys to pick a piece for me. Let's do it. So now let's put together that outfit. Now, when it comes to, when it comes to curated stores, unlike Goodwill, everything is good. So it's going to be a bit of a challenge trying to put together an outfit because everything's so, so nice. Since I believe pants are the most important part of an outfit, I decided to start with that. And we came across a lot of good options, patchwork jeans, striped wide fitting pants, double knee denim. But the problem was none of them were my size. We had a small window of items to work with. Y'all discriminating on size 30, man. Best seller guys. That's why you got a limited option, but that's fine. We're doing too well. Oh, hold up. Some bootcut pants. And after getting humbled, two pants caught my eye. This light wash bootcut denim and these faded rust orange CDG pants. So I think this is the perfect time to tackle that challenge. So we hit up our boy, Kevin. Kevin! Let's see what he picks out for us. All right, Kevin, I'm stuck between these two. All right. CDG pants, some light wash bootcut denim. Okay. You got to help me pick an item, man. So you can do one for this. You can do one for this. I'm going to pick whatever I think looks best. So I'm going to see over here real quick. Now, while we're trusting our man, Kevin, over here with the fits, there's actually a level 3.5 that you guys can use while I'm working on this fit. And that is why we partnered with Shop for this video. Let me show you. Most people probably recognize Shop for tracking their packages, but did you know you could actually shop on Shop? I didn't either. And look at my feet. There's a lot of gems I never would have found myself. And since we're still on level three, there's also other secondhand curated thrift stores on Shop. So we're also going to look for an accessory for the fits using the Shop app. But let's check back in on that employee pick. Nice little graphic here. It's like nice and soft, nice and broken in. And as much as I love the process of thrifting, checking out pieces, as you can see, we're just limited to this store. But instead, you and I can browse a bunch of different stores and brands all in one place. And more importantly, the feed becomes curated to your taste. So my feed is basically clothes, clothes. Oh, hey, mattress. I see the jewelry collection that I designed. And take a look at this. Here is another curated vintage store. So if you don't have one of these curated stores in your area, well, now you can just hit follow and stay in touch with other secondhand curated stores. And this is exactly what I like about the thrifting process. Just finding cool items. Only this time, we're using our phones. Makes it so much easier. Now, I've never heard of these brands before. And it looks like they've got some really good secondhand pieces. But also, since we're at Layers Chicago, y'all can follow them on shop if you can't make it out to the side to shop in person. So while Kevin is still looking, I actually picked up this wallet chain from a secondhand store through shop, which we will add to the fit. Now also, my favorite brands, checkout, and all my orders are all in one spot. And at the same time, you and I can get discounts exclusive to the shop app and earn shop cash on eligible purchases. Just look out for this purple badging or check out the deals tab. And it looks like Kevin found a piece. Let's see what he picked out. Pink and the red kind of goes well with like the light wash denim. Yeah. Yeah. I think we'll do that. Lock in with this one. Yeah. Is that a drink? Yeah. Is that alcoholic drink? Yeah. I don't drink. Oh, you don't drink? Not bad. Not bad. So if you want to see what shop finds based on your taste, download the shop app today. Now, Kevin thought the Jaeger shirt was fine, but he wanted more options probably because I said I didn't drink and then something crazy happened. Yo, somebody got hit. Oh, snap. Oh, right in front of the Supreme line too. So yeah, a scooterer, he hit that car that was trying to turn in. I don't know who's at fault, but most likely it was the driver. If y'all scooter or bike out there, cars don't care about you. So be careful out there. Anyways, Kevin was stuck between these two shirts for the CDG pants. So we called in some reinforcements and we got our boy Wes for a second opinion. I think it matters about the fit more than anything. Yeah. Yeah. Yeah. Cause that's like a more narrow, right? I'd go the more boxy one. All right. Add a phone in front, add a phone in what? Shout out to Wes. Appreciate you, man. Chicago Bulls with the light wash denim, alcoholic drink with the CDG pants. I don't drink, but I'm gonna roll with this one right here. I think I like the colors. How should we complete the outfit? I then looked for some accessories as I didn't want to hide the shape of the items with a top layer. So I got some recs again from Kevin when he decided to take us to the display case. Ooh. And we went with this stone cold ski Boston cap. I then checked out at a price of $138. Still pretty good for a full outfit with the hat surprisingly being the most. I looked it up and these stone cold hats are crazy. Interesting how the vintage market works. Anyways, here is the outfit. Yo, this outfit is clean and there's like, it's more on the slim side, but it still looks great. Not everything has to be real baggy, you know? So yeah, everything feels cohesive. The pop of orange on the hat matches the pants. The black accessories, black boots match the black graphic on the shirt. The wallet chain matches all the other accessories. Great fit. Curated thrift stores, highly recommended. Now since this was my first time in Wicker Park, I just wanted to enjoy the vibes a little more. And we saw so many other thrift stores, this really nice coffee shop with this old school back to the future theme. I can see why people like this place, but I was itching for something different, which is when I came across this store called Happy Belated Clothing. So welcome to level four. We are at Happy Belated Clothing and what makes this level four is how unique it is. Every item is imported from Japan and it goes $10 a pound. Anything you get. I've never been here. Hopefully they got some good stuff, but we've got the thrift challenge board and for here, blue's my favorite color. Let's see what number six has. Okay, we got thrift roulette. Now this is when I will have to close my eyes, scroll through a rack with my hands, and whenever my cameraman says stop, I'm going to have to grab that item and make that a part of the fit. But for now, let's head inside. Now walking in, you'll find a completely different storefront than anything we've seen in this video. Stuffed animals, a disco ball, more stuffed animals, cool art pieces, and the store manager, or at least one of them. And of course, tons of clothing stretching all the way through this hallway into the back of the store. And mind you, if you ever come to a store like this, because every item is imported from Japan, you want to size up. But also if you're on the shorter side like me, five foot seven, all of their items are going to fit much more proportionately. Now, unfortunately, a lot of the men's items was towards the front of the store, so I think this is a perfect time to start the fit off with thrift roulette. I'm going to start three, two, one, go. Ooh, okay. Oh, this is Uniqlo's Puptec size XL because we're in Japanese sizing. This probably like a size large US. So let's try it on. Yep, definitely glad that this piece was from Uniqlo. And after trying it on, it brought a smile to my face. So now it was time to gather the rest of the outfit. After seeing a ton of other pieces that definitely would have cost maybe 10 bucks. And let me tell you something, it was very tempting, but we got to complete the outfit. So then I found this simple top also from Uniqlo. I then stumbled upon this clothing rack with a ton of pants options. And I ended up picking up these black Hakama style pants. And look at the hardware there. That's actually pretty sick. I think I might roll with this. It's adjustable too. And then this trucker hat as an accessory. Time to check out. Have you all been here before? No, this is my first time. Oh, cool. Yeah. I moved here last year, so I'm just checking everything out. When did you guys open? Like a little over a year and a half ago. Oh, really? It's very new. And then we've got a little scale here. Yeah, totally. We got the hat. Yeah, we got by the pounds. Oh my. What? Only 3.85 pounds? Yeah, totally. That's crazy. For a full outfit. Yeah, 42 bucks after taxes. Guys, they're so chill here. So chill here. 42 bucks for this is crazy. And yes, that smile on my face says a lot about this place. Such a cool experience and only $10 more than Goodwill. Here's how that fit turned out. Already this fit alone, it looks nice. It's my first time wearing it. And it just goes to show how much pants affect an outfit. But let's try on the jacket with it. Ooh, okay. If y'all can find a Japanese thrift store, try and find some Hakama style pants. They do a whole lot. So happy belated, sleeper. But now on to level five. And guess what, guys? We brought out the family. And we are at Vintage Fest. I know it doesn't look like anything right now. It's about to, I just felt a raindrop. It's about to pour like crazy and it's going to get wild in there. Now we still got to do the fifth challenge board. I got to do this before it starts pouring. We're on some grass right now. It's green. Why don't we go? Number two, price wheel. Okay. So this, I have to grab the price wheel. This is where we spin this price wheel. Whatever we land on, that's going to be our budget for one item. So let's go for it. Ooh, 25 bucks for one item. I mean, I'm sure there's gonna be something more affordable. Let's head inside before we get drenched. Anyways, as we walked inside, it was overwhelming in a good way. Illinoisans just enjoying a community thing. And it's beautiful to see how one event brings together so many people. Earlier this summer, they were at Navy Pier, but currently we are at the DuPage County Fairgrounds. But yeah, the founders host these events that provide the opportunity for small businesses all around the Midwest to sell their secondhand stuff, not just clothing, because there is a lot, but it really helps out these small businesses. Plus it's a really cool event. Now for this particular event, you'll find a massive warehouse full of small businesses, a center stage with its own boutiques, food trucks on the outside, and a separate building with even more stuff. There are so many options, so I have high expectations on what I could find. All right, we've got some kicks over here. Got the Union LAs. I got these ones too. And there's some good stuff in there. It's like almost too much. I don't even know what to get. This was just the first couple of minutes inside and almost everything was a gem or nostalgia bait, which I quickly fell victim to. If you remember any of these, you're a real one. Game Boy, Pokemon Gold, Red, Blue, Emerald. You know, there's like 200 bucks secondhand nowadays. That's right. Pretty wild. Torchic was the best starter for third gen, no debate. Got an old school PS1. Bro, life was better when there was cheat codes. Cheat codes in books. Okay, old PS2 games, old PS1 games. Burnout 3 is a good game. Yo, I grew up with this game. Smackdown, here comes the pain. Dude, this is the greatest wrestling game of all time. That's right. If you didn't grow up with this game, I'm sorry. You did not have a childhood. And after some more walking around, my son trying to take off some clothing from the racks, I found some nice vintage watches, this booth that has these hand-stitched poster designs, vinyl records, and even more cool jackets. But I'm thinking for our challenge item, we find some pants. What better place to find pants than Vintage Fest? I'm sure we'll find something good. And as luck would have it, we found a boutique that fits our budget for the challenge item. Every pant was under $20. Crazy steals. So we ended up with these camo cargo pants. I'm not sure if you guys can see them, but trust me, it's there. So thrifting challenge item, check. And as much as I want to shop for my own self, we got to complete the fits because at this point in the search, I wasn't kidding about that weather. Yo, guys, I think, I think we're trapped in here. Yeah, guys, honestly, it was quite terrifying. We got some tornado warnings. Guys, I'm from the desert. I'm not used to tornadoes. Anyways, back to the hunt, I'm thinking we should get some sort of top. Since we're at Vintage Fest, I feel like we might as well get something that represents Vintage Fest, you know? I think this thing's pretty cool. Which we did end up picking up. This was a crew neck with a nice graphic. And I'm thinking to compliment that military look from the cargoes, a utilitarian jacket might be the move. Yo, these old school leather jackets are clean. Harley jackets. Look at this one. 140 bucks. Got some vintage Carhartt. Already did the Carhartt things in these probably. Dude, there's just so much stuff here. I'm overwhelmed right now. So after some more walking around, I then picked up this black chore jacket. It was one size, but I love the shape of it, love the design. And I thought it would pair really well with this outfit. And the fit's pretty solid. Only 95 bucks. The workwear, the cargo pants, the vans. Level 5, incredible. Now, this is just in my state of Illinois, but for your level 5, this could be any big event or pop up or community gathering of small boutique shops. Back when I lived in Brooklyn, they had this flea market every weekend right underneath the Manhattan Bridge. I guess that makes it my second time thrifting as an adult. And I just find these events so wholesome and necessary. You know, with AI, social media, and just the modern world in general, people crave these types of events. And to go full circle, Illinois Vintage Fest started as a garage sale, level 1, with just a bunch of friends. And look at what it's turned into. If it can be done here, it can certainly be done in your community. And you just might be the one to start it. So here are all the outfits again. Which fit did you like the most? Let me know in the comments. And hey, since you made it this far, why don't we kick it a little bit longer? Do you remember some of these fashion brands back in the day? Well, check this video out.