Fashion psychology: What makes an outfit look cool?

Hey y'all, hi. Okay, what makes outfits look cool? Coolness is such a pervasive, abstract yet graspable quality that my not-yet-two-year-old has already started using it to describe things when he likes something about them but he doesn't really know how to explain it. Like just the other day he said he wanted to walk on our cool new rug. He clearly already knows what it means even though it's so hard to define, or at least he already knows how to use it. Cool is a slang word but it's incredibly pervasive and endearing. And in western fashion over the last century the concept of coolness has had quite the run. Originally as something counter-cultural, something only possible like for the rebellious, and then eventually entering the mainstream and becoming marketable and marketed, and because of that simultaneously much more accessible and harder to define. Because now in a way there's coolness everywhere, like at every level of luxury, at every price point, to the point where it is very much in, as they say, the eye of the beholder. What looks cool to one person might look sloppy to another, and what looks cool to that person might look buttoned up or overplayed to the first person. So as I always try to do today I'm thinking out loud about how to make this fashion concept accessible across all of our lives, with all of our different bodies, life stages, lifestyles, and personal styles. What makes an outfit look cool? Not specifically, because what works for you, like a specific garment that works for you, is not going to be the same thing that does the trick for someone else. But how can we generalize and then kind of reverse engineer to think about, for each of us, combining the clothes that we already have and wear in a way that is especially cool? Now, before we start, I have to acknowledge that the concept of coolness has an etymological and cultural context that goes way beyond the scope of this video. Even though a nuanced use, like a non-literal use of the word cool goes as far back as Shakespeare and Chaucer, it was really Black jazz musicians in the 30s and 40s who started using the word cool in the way that we use it today. Like so much slang, and like so much of what is even cool, like aesthetically cool, musically cool, I would say posturally cool, like what is a cool attitude, like so much of what is cool, the word cool has its roots in Blackness. And I'm not qualified to really unpack and like deeply examine the specific links between those roots and what feels cool now in different settings. There are people doing that amazing academic work. This video is more of a zoomed out survey of fashion tools that might work for anyone. But it's important to acknowledge the history and the complexity. And funnily enough, I recommend the Wikipedia article on the aesthetic concept of coolness, which is surprisingly thorough, and the work of Robert Ferris Thompson, which I will link down below. Let us now get into the meat of the video. This video is sponsored by Quince, and today I actually want to talk about their homewares, the aforementioned cool new rug. So Quince, as a lot of you know, has a factory direct model that reduces margins and overhead costs, and that is what keeps their prices so low, especially relative to the quality of the goods, which I've talked about a lot on this channel with regard to their clothing and jewelry. Amazing prices for 100% linen, cotton poplin, 14 karat gold jewelry, and always at Quince with those design nuances that make the biggest difference. Quince has branched out gloriously into home goods, and just like with the clothing, they reliably use quality materials, a lot of pieces are made with natural fibers, and there's real attention to detail in the designs. I've been very impressed by their rugs, and this one is perfect for our hallway. I was looking for something with a bit of pattern interest, but neutral and not too busy, soft to walk on, but flat enough to work with our louvered doors. This feels great underfoot, I love it, and my friends, it's 100% wool. We also just got a set of their Japanese knives, which are absolutely beautiful, cut everything like butter, they have made meal prep such a pleasure. Some of the best value I think in Quince clothing is their leather goods. The leather jackets are so well executed and luxurious, and that really translates to homewares as well. They have some amazing leather travel accessories, like this duffel bag and their toiletries bags are really well designed. The same goes for linen. I'm obsessed with this garment washed linen bed cover. It's one of those heavyweight single layer linen summer covers, you know, lighter than a quilt but much heavier than a sheet, which is my perfect bedding for hot weather. All of it has the qualities that I like the most about Quince clothing. Their use gorgeous materials like wool, linen, and leather, and like a modern sense of design. And I love seeing how that remains true in their functional items for the home. So thank you to Quince for the sponsorship, and of course I'll link this exact duffel and rug and linen cover, and I'll put as much detail as I can in the description box about what the pieces are like in person. Okay, so what makes an outfit look cool? I think it has something to do with the interplay between boldness and restraint. And let us talk first about boldness. So sometimes I look at an outfit or a picture of an outfit and what's making it look cool is something bold. This can be one exaggerated piece, as I've talked about often, like a huge chunky scarf, a statement coat, a sculptural bag, a pair of heels worn with an otherwise casual outfit. That's a great trick to make something look really cool. And the simplest way to employ this principle yourself is when you're putting together an outfit, ask yourself, is there one bold item around which I can build this outfit? Or, you know, if you were already getting dressed and it's not working, can I just add one very bold item to this? So say you're wearing a t-shirt and your skinny jeans, and you're going to be walking a lot today so you just put on your sneakers, and you need like your basic tote today for practical reasons because of what you're going to be doing. You're about to leave the house and you're just feeling blah, like not quite as cool as you would like to feel. You don't have to change everything. My first thought is just switch out the skinny jeans for a pair of kind of dramatic wide leg trousers that you usually save for more formal outfits or fancier occasions. That's a very specific example that of course won't work for everyone, but the takeaway is universal. One bold choice can make everything else seem cool. Now let's talk for a moment about restraint. Sometimes, I would say often actually, I look at an outfit or a picture of an outfit and what's making it look cool is the deployment of restraint. Monochromatic outfits, of which I'm a huge fan, are actually all examples of restraint. It's a restrained color palette. Wearing all black, which is, you know, somewhat universally a reliably cool choice, is an example of the most extreme color palette restraint. Tight tailoring, like a very sleek tailored coat or a fitted suit, the polish and impact that that exudes, that's a kind of silhouette restraint. And I'll tell you a story about this. Recently, I was going on a trip for a couple of days and I needed to take a light jacket and I was trying to choose between a really dramatic drapey oversized linen blazer that's like very fashion. That would definitely have been quite a bold choice to take as my one jacket to wear with all of my outfits. And the other option was a simple cropped, still beautifully designed, actually it's from Quince. It's my Quince Windbreaker. I love the silhouette of it and the design. It still looks chic, but it's not bold. It wasn't a bold choice. I was mostly wearing all black on the trip and on the day I was trying to decide, I was about to leave, I was trying to decide which jacket to take with me and I was wearing all black. So I put on the oversized blazer and it was like very fashion. And then I put on the Windbreaker and I was saying to Joe, which one of these do you think I should take on the trip? And he was like, well the black one looks cooler. That was how he described the quality that it had, even though the oversized blazer was very bold and very fashion. He was like, you look cooler in the Windbreaker, which is a much more utilitarian garment. But I think that that was because of the deployment of restraint in the outfit with Windbreaker. It was a tighter silhouette, it was less of a fashion risk, but also when I put it on, I was then wearing all black. To Joe, I just looked cooler. He couldn't really explain why, but that was his immediate reaction, even though I was thinking of the oversized blazer as like the really cool option. So the simple way to deploy this concept by itself in your life is to just think about if there are ways that you can sort of simplify or pare back your outfits. You know that old famous saying of Coco Chanel, before you leave the house look in the mirror and take one thing off, kind of a way of saying just tone it down a little bit. Our instinct is usually probably to do too much and doing a little bit less is going to get you there. Going with an unfussy choice instead of a fussy choice, leaning into cleaner lines, fewer colors together in a single outfit, that can be really powerful. Fewer pieces in a single outfit, just eliminating the bells and the whistles. Now, at this point in the discussion, these might seem like opposites and like opposite strategies, opposite pieces of advice. And that's what makes this question so interesting. Utilizing boldness, which was the first strategy, in that case you're adding something to turn the impact volume up. And using restraint, it seems like you're turning the impact volume down. And you would think that those two wouldn't really talk to each other, right? You're just choosing one or the other. I actually think they talk to each other quite a lot. And I think that's where the magic is. I think that what really makes an outfit look cool is not just choosing boldness or choosing restraint, like choosing one as a trick and leaning into it, but rather in the interplay between the two of them. For example, one of the things that makes me feel the coolest, like if I am going somewhere and I'm like more than anything else, I really need to feel cool and I really need to look cool. My most reliable strategy is to wear all black and have my clothes be pretty fitted, and then big chunky black boots and like a rugged or oversized black jacket, like a leather jacket. So in this case, the color palette is restrained, the formality level is a bit restrained as well, right? Because it's kind of laid back, doing a little bit less. But the boots and the jacket are bold, very bold. And then the overall look together has a high level of impact, a dramatic quality that is also bold. So the boldness and the restraint kind of end up dovetailed together. And I think that the opposite of this example also works. So let's say your boldness is in color and you're wearing something really colorful or a bunch of colors together. To apply restraint to that, you might simplify the silhouette, have it just be palpably laid back, draped, informal, keep hair and makeup pretty effortless. Here's an example from the tumblr account New York Looks, which a lot of the imagery that I sourced for this video is from that tumblr account, so I'll definitely link it down below. And that's where I got this image. Some of these choices are bold, right? Color, pattern, texture. But there's so much restraint in the styling. Everything is loosely layered, instead of anything being tucked in or buttoned up. Hair is loose and long, no noticeable makeup, shoes are pleasantly dirty, no bag, no heels. In a way, I think what we're seeing is that these two qualities that seem opposite, they kind of feed each other. If you show the amount of restraint in your look that's necessary to really impact the way that it comes across, in a way then the restraint and what it leads to has become dramatic in its own right. So it's like the restraint has become boldness. And if you do what I was suggesting at the beginning, if you choose a single extremely bold piece to like carry your entire outfit, in order for it to stand out and really do its work, like really do its utmost, you often have to show restraint with rest of your outfit. The more you think about it and the more you actually act on it and play with it, the more they start to speak to each other and kind of blend into each other. It's like it becomes circular. I think though depending on how you dress now, what you have, what you need, what your instinct is, what comes naturally to you, and what's hard for you, it might be that either boldness or restraint on its own is the kind of mental springboard that you need to inject some cool into your current styling. But if you really want to lean into it, I think that the most fun can be had by thinking about how boldness and restraint are affecting each other in a single outfit, and what you can change about one by tinkering with the other. So what do you think? What makes you feel really cool? And is there anything that I've said today that correlates with what springs to mind for you? What do other people wear that makes them look really cool to you? And maybe there are some of you with a more academic understanding of aesthetic cool, its history, its complexity, the place that it occupies in the zeitgeist and in the English language, who can shed some light on whether or not this idea that I've come up with, which is the interplay between boldness and restraint, is actually like traceably a legacy of the cultural evolution of cool. I would love to hear your thoughts, as always. I've always had the best commenters, the most brilliant comments, and the most brilliant comment section, but you all have been absolutely smashing it lately. Like every time I get down there in the comments, I'm like, these really are my people. So do weigh in. Thank you for being here and spending this time with me. And don't forget to take extra good care of yourself so that you can be the most effective version of yourself as you do your work in the world.