The Secrets Behind Carolyn Bessette Kennedy's Timeless Style

You know that woman who always looks chic, she doesn't look trendy, she's not overdressed. She just looks right. Well, the difference between her and everybody else is so much smaller than you think. Hello, gorgeous girl. Welcome back to my channel. And if you're new here, hi, I'm Tracy. I'm 51 years old and I'm such a lover of fashion, style, fitness, wellness, beauty, and skincare. Those are things that you like too. Welcome home. You're in the right place. Make sure to tap on that subscribe button and everyone tap on that little bell so you always know when I have a brand new video that goes live. Right now, I would say that collectively we are all once again in a complete chokehold over Carolyn Bessette's fashion right now. And if you haven't watched Love Story right now, which is streaming, I'm watching it on Hulu. I think it's also on Disney Plus and maybe FX. You need to watch. But I have always, yes, since the nineties referenced Carolyn Bessette's fashion. It was just forever tattooed in my mind because I'm such a lover of nineties minimal fashion and I was living in New York City at the time and it just brings me back to those days. Oh my gosh, I could talk about this forever. But here's the thing. We like so often to say that her fashion was minimal, but I say, in fact, it was actually something different and actually something so much more powerful. It's that everything that she chose to wear in her unfortunately very short life was intentional. The coat length, the neckline, the shoe choice, the bag choice, how she even wore her hair. Every single detail was made with some intention. And truly that's the difference between looking dressed and looking chic, especially now that we're over 40. So let's dive in and break it down so that all of us are really making it easy for us to look chic, to be that woman that is so put together and looks amazing without spending a ton of time or effort. The first thing that we want to remember is that chic is intentional. Dressed is accidental. All of us have to get dressed in the morning, right? I mean, it's inevitable. You have to put on some clothes in the morning and that can be done with intention or it can be done accidentally. You just put on the first thing that you find or your favorite pieces. But when we're thinking through the lens of intentionality, that's when we are so easily just up leveling our look. And it's actually quite easy. It starts by asking yourself a few key questions. Does this silhouette actually work on me? Does this color flatter me? And this is a big one. Does this feel aligned with who I am now and with who I want to be? You know, we talk about this a lot on my channel, kind of presenting that best version of yourself. Does what you're wearing actually align with that as well? Now look, in your twenties, you can just buy what's cute. I did it. I didn't have any money in my twenties and I just wore whatever I thought was cute, what was on trend. And with my little 20 year old body, it usually did look actually pretty cute. But when you're over the age of 40, you are now building a wardrobe. And that's why I know I keep bringing it back to Carolyn Bessette Kennedy, but it's like her clothes, you can wear them now 30 years later and they still look current. That is the power of intentionality. So chic women don't panic purchase. They curate. They consider their lifestyle. They consider cost per wear. They think about does the piece that they're thinking about buying actually work with items that they already own? You know, I have a friend who's quite stylish and she told me, you know, I will only buy something if I know that I can wear it with three other items in my wardrobe. Such a small, small thing, right? But it makes a huge difference because then you're not just going to have a bunch of random pieces in your wardrobe. You will be curating a look, a theme, a vibe, and intentionality is truly the foundation. Now, this is a concept that I had been practicing, but I didn't really realize that I was practicing. And I love this so much. And that is that chic thinks in columns, dressed thinks in pieces. So let me explain. I've talked about this many, many times on my channel, but one of the best and easiest ways to really uplevel your look and to look more chic is to dress in either monochromatic or in tonal dressing, and in my opinion, tonal dressing is actually so much easier than monochromatic, all black, all cream, all Navy, all chocolate brown, or even soft layers in the same tonal family. And like I said, tonal dressing is really one of my favorite ways to do it because you do not have to have an exact match when your eye isn't interrupted by harsh contrast, the look immediately looks more expensive. Now, when I was in my twenties living in New York city, I was broke, broke, broke, broke, broke. So I would always wear just all black because I knew even at 20, when I was putting a pair of black pants on and maybe like a little mock turtleneck top or a little black t-shirt, probably a baby t-shirt, it was the nineties and you know, whatever shoes I was wearing. I knew that I looked a little bit more expensive than the probably $20 item that I was actually wearing. So when you want to look chic thinking columns of color, is there a bit of cohesiveness here? Do these colors actually work with me? Are they sort of in the same family? And a great way to add a little bit more interest is by including texture in those same color families. You know, think about it. If you're wearing like, uh, maybe, uh, this, this jacket that I'm wearing, right, I have a white t-shirt underneath, but if I had like a brown leather skirt, or I have like a brown kind of a satiny sort of fuller skirt, that will look so much better. They're not the same color, but they're sort of in the same tonal family. That's going to make it look a little bit more cohesive. And then if I brought in sort of like, I have a beautiful brown pair of boots that I actually bought probably 10 years ago because of Carolyn Bissette, they would, that would kind of pull the more camel color. So again, your eye isn't like crazy, not knowing where to look, but it looks cohesive. Now this is a big one for us ladies, and I really want you to take this one in. Chic is about fit. Dressed is about size. You know, how many times have you thought, oh, I'm not going to buy that because that size is too big, even though maybe the pair of pants actually don't fit you. Whereas if you actually upsize a little bit more and maybe got the waist tailored and got the pants taken up a little bit, the fit would look like it was made for your body. So hear me now, especially over the age of 40, we do not want to be run by the label on our clothes. If they don't fit, just buy another size. It's not a problem with your body. It's just the size of the clothes. But a few things also, you know, I love oversize. I love that look of like something really oversized. And I know for some people it's really polarizing, but you know, for instance, I bought this like leather bomber jacket specifically because I knew that it was an oversized look. Some people hate it. I personally love it. And I think that that is really an intentional choice. It is very obvious that was intentionally oversized. It doesn't look like I'm wearing my husband's jacket, but it was an intentional choice. Now I love wide leg pants. I love that look of fluidity and draping and movement in your clothes. But again, because I'm only five foot two and I'm a relatively petite girl, I often will have to get the waist taken in, the pants taken up so that they really fit my body. Again, it's not the size. A lot of times I'll buy my pants a size larger because I want a little bit more of that draping, that fabric, that movement. So become friends with your tailor. It doesn't have to be super expensive, but it makes a world of difference. I recently just bought a skirt and it was like a size eight, which I'm not generally a size eight. And I could have worn it on my hips, but I was like, you know what? No, let's bring this up. Let's get the waist taken in. And I even had like around the hips taken in. I did the same thing with this beautiful kind of mock croc brown skirt that I have. I absolutely am obsessed with this skirt. But I've lost a couple of pounds and I realized it was sitting lower on my waist that I wanted it to. So again, same thing. I brought it in and for like $40, it's like a new skirt and it fits like it was made to my body. So use your tailor and remember that fit is actually quiet power. Chic actually styles jewelry and is intentional about her jewelry and dress just wears it. You know, it's so funny. I have a friend and I feel so badly, but she really loves like statement earrings. And in my opinion, they just end up a lot of times looking cheap and I'd rather she take that money and invest them in some pieces that are timeless, that are chic, that are elegant. And yes, they can still be fun. So choose an earring that actually works with your hair, with the way that you're styling your outfit. Choose rings that actually mean something for you. You know, I often will wear a signature necklace and it's really special to me because it has my grandmother's wedding band and it has an L for my daughter's first name. Those choices can take a basic and kind of boring outfit, even if it's jeans and a t-shirt and really elevate it into something chic and again, intentional. And I like to think of jewelry as sort of the punctuation on the outfit. Look, right now I'm basically wearing jeans and a t-shirt. I threw a little jacket over it, but I was very intentional with my jewelry choices and that is really the punctuation on the sentence. So for instance, today, the earrings that I'm wearing, I love that they're so fun and they're actually different and that's intentional. And these are from the brand Ideal. What immediately stood out to me about Ideal is the quality. They're designed in Antwerp, which is actually the diamond capital of the world. And every piece passes through multiple skilled hands before it even gets to you. And you can really feel that level of precision. And I also love that it's a 90% female run company. So we love supporting the girlies. They use the top 1% of lab grown diamonds. So you're getting a true fine jewelry look without the traditional markup. It really feels like legacy jewelry. And I know that these are favorite pieces of mine and I will be wearing them for years. And what's really fun about Ideal is the modularity. They are not one note pieces. You can stack them. You can layer them. You can change them depending on your mood, your neckline, or even just your vibe for that day. Okay. So let's just talk about what I'm wearing today. First of all, I got this little ear cuff and I've been kind of thinking about like, should I start using some of the holes that are on this side? And then I was like, you know what? Why don't I get a cuff? So I was so thrilled to see this little diamond cuff. It's so gorgeous. I'll leave the names of all the pieces that I've chosen on the screen here. And then these earrings, I have two of these, but I decided today it comes with like a diamond stud, but then it has a little huggy around it, which looks so, so cute. And then this one gives that look like I put in a bunch of studs, but it's really just one hole and then the diamonds go up. And what's cool about this also is I could wear it going up my ear like I'm doing today, or I could kind of choose to just have it hanging down like that. So it's so, so cool. I gasped. I actually gasped when I opened the package, when I got my pieces, but these feel like everyday, but chic-er. They're interesting. They're cool. I don't know. It just makes me feel like I'm having a little bit more fun with my jewelry, which I love, and it actually really works with my rings that I wear on a daily basis. So we love that. Jewelry is never the headline, but it is the punctuation. And that really is the difference that makes it all feel intentional. And that's the secret that chic women know. So if you want to check out Ideal, I will leave all their information down below in the description box. Truly, these are gorgeous. And you're going to be seeing them on my channel a lot. And if you're watching me here on TV, you can scan this QR code so you can check out Ideal for yourself. A chic woman is aware of the trends, but a dress woman is ruled by them. Now, here's the thing. And I know that trends for a lot of people can kind of be very polarizing. Some people are like, I don't care what's trending. I'm just going to wear what I like. And I love that. However, I do think it's important to know, to have just a subtle sense of awareness of what is actually on trend. It doesn't mean you have to wear it, but that you have that awareness that maybe certain silhouettes or certain colors are just of the moment right now. Again, it depends on you, your coloring, your body type, right? Low rise pants, they might be on trend. I'm not going to wear them. I don't like them. I'm only five foot two. I need a high or a mid rise so that my legs don't look like little stumps. But my point is having that awareness of trends. And that also makes it fun just knowing like, Oh, it's funny. You know, olive green right now is really having a moment, but maybe it doesn't work for your skin tone and you can choose to opt out. I have a great example of this, cardigans. I feel like every woman has a cardigan. Well, if you have that waterfall sort of no button longer cardigan or even worse, the cardigan vest, that to me sort of screams 2016. We all had them. We all love them. I totally had one, but now in 2026, a cardigan is very chic, but it has a slightly different silhouette. For many, it's a crew neck or it can be a V neck, but it has a slightly more cropped length. Now it doesn't mean that your tummy has to be sticking out, but that you can either tuck it into your pants or that it just lands right on your pants or at least above, you know, your rear end, right? So that's those slight, slight differences are what's going to make you look more chic than dated. So this is one that you might want to write down. Chic women update their shapes, not their identity. The next one is that chic women consider hair part of your outfit, especially if you have longer hair, this is a huge one to consider. Hair is really an accessory, right? So for instance, we were talking about the jewelry that I'm wearing today. It was not unintentional that I decided a little bit of a side part pulled this back. Why? Because I want to showcase these fun little earrings that I'm wearing. I want to show the silhouette of the jacket that the collar sort of stands up on its own, right? If you're wearing something that's like off the shoulder, in my opinion, either very loose, kind of like carefree, like I didn't do my hair at all, but you totally did your hair is a great look or kind of wearing it up. But in my opinion, wearing it up, especially if you're going to like a formal event so that it's a little bit looser, just slightly undone is what's going to look a little bit more chic and a little bit less stuffy, to be honest. So think about it this way. It's a really easy kind of formula that you can adopt. If your look is more structured and formula, let's say you're wearing suiting, I might not do one of my very much signature looks, which is sort of the slick back bun, but you know, um, the point is I will usually, if I'm wearing like a suit or something a little bit that goes a little bit more masculine, I probably want my hair to be a little bit more feminine, a little bit more slightly undone. But if you're wearing something that's way more casual, I don't know, like maybe you're wearing like a loungewear set or something like that, having your hair, if you're going to be wearing it to the grocery store or something like that, you might want to just make sure that your hair is combed, that it is neater, that it's just looking a little bit more put together, or even just like throw on a headband so that it just looks like, yes, I did actually choose this and I thought about it. I didn't just roll out of bed. Chic women think about things like head to toe. Nothing is random and it's really a thought, a consideration. Think of Carolyn Bessette. We're going to bring it back to her, right? She would have her hair loose and flowing and, you know, flipping that hair all over the place, right? With her natural texture, but while wearing something a little bit more structured, that white button up top with that kind of long sort of slinky skirt. Right. But then when you would see her on the street with maybe like cropped jeans and a little t-shirt, she'll throw a little triangle scarf in her hair. A little Jackie O'Nod, which we also love. We see you, Carolyn. We see what you were doing there. But my point is every single choice was made with intention. Oh, I could talk about this one all day long. And I love this because this is something where if you literally spend $20, you can completely change your outfit. And that is chic understands the power of sunglasses. Sunglasses to me are like the sprinkles on an outfit. Now, yes, I live in Miami. It's sunny every single day. So I do need sunglasses, but I truly, at this point, have an entire wardrobe of sunglasses. And that again is intentional because depending on what I'm wearing, what the silhouette is, what the fit is, what the color is, I want to make sure that those sprinkles of the sunglasses really match the vibe. They can really elevate even the most simple outfit and even better when you have like a no makeup day and you just can't be bothered and you kind of want a high, sunglasses are it. And my favorite thing is that you do not have to spend hundreds and hundreds of dollars on sunglasses. In fact, my most recent purchase of sunglasses were about, I think, $22. Of course, I will leave them linked down below. These are a very much designer inspired of a brand of sunglasses where I almost fell off of my chair. The sunglasses were almost a thousand dollars. They were like $960. I'm sorry. I have a problem. Like I'm just not going to spend that much money on sunglasses. But of course I found a pretty much exact dupe for under $25. But my point is a chic woman understands this. Think of Jackie O, signature, large, round sunglasses. Think of Carolyn Bessette, oval, right? That sort of minimal. Now it depends on you and your face. I don't look good in small sunglasses. So whenever that comes around and you know, fashion is cyclical, those smaller sunglasses, I just skip them. I might do something a little bit more elongated, but it will still have to be a little bit larger. Cause honestly, I think I probably just have a big head and a bigger face that just needs a little bit more coverage. So play around. You don't have to spend a bajillion dollars. Check out my links cause I will leave some of my favorite pairs down below in the description box. But sunglasses, again, they really are the icing. They are the sprinkles on your outfit. And it really makes you look again, that you intentionally chose them. And it really makes it look like you're putting together a whole look, even on a very easy, casual, no makeup day. Chic knows the shoe equation. And yes, honey, we are talking math here because there is shoe math. I've said it before on my channel, but I hate the wrong shoe theory. No, no, no. Wear the right shoe. Cause this can really make or break your outfit. But here are some of the equations on shoes that I think really matter. If you are wearing a jean or a trouser, you again, don't want to break the line with your shoe. So a boot, something with structure or heel. I personally love a more pointed toe look because again, I am shorter. But the main point is again, thinking in columns, you want to keep that length. If you're wearing a skirt, a pencil skirt, a midi skirt, which is very on trend right now, a boot, again, something that has structure or a pump or even a kitten heel, or you could even do a loafer, again, everything chosen with intentionality. When I'm wearing pants or jeans that showcase my ankle, that's when I love pulling out my loafers because again, that little bit of ankle showing for me at my height, it makes the shoe look intentional, not like I accidentally just happened to throw on the jeans and then just chose the shoes, but it's this length of pants with this shoe together, it looks chic. It looks like a choice, not an accident. Some outfits need a heel, some choices need a loafer, some you're just going to look best in a sneaker that is well chosen, but understanding proportions is absolutely everything. In fact, I have a whole video all about outfit formulas, and that'll help you just kind of get dressed quicker and easier and have that more chic, elevated, timeless look. So after this video, you can definitely check that out next, but just remember this, shoes are architecture and it really will either make or break your look and it can either look great, cohesive and chic or like what is going on there, something is off. And the last thing I want to remind you is that chic is cohesive. Just being dressed often looks busy. I am looking in the mirror when I say this, I used to wear all kinds of like crazy prints and colors and the more like fun items in my wardrobe, the better. But now at 51, I'm finding myself so much more drawn to pieces that are more simple, that are chic, that are timeless, that just really focus more on fit and quality than busyness. And again, bringing it back to Carolyn Bessette, that's exactly how she chose her wardrobe. I saw something interesting. They were like, maybe she wouldn't have made those choices if she wasn't a Kennedy. But I actually kind of disagree because I think that her individuality, her creativity, it still came out with some of the shapes that she was wearing in like that pop of a bright red lip and some of those like more fun items that she had, nothing about her wardrobe was basic or boring, but every single thing was intentional and that is what's going to take you from dressed to chic. So if you finding yourself having like visual chaos in your looks, have a friend over, get her a coffee, a matcha, or even a drink and say, come over or do it yourself, I always, always use my phone and I take videos of my outfits because sometimes the mirror lies and I'll think something looks fantastic. But then if I watch it on my phone, I'll be like, Ooh, that actually doesn't fit or doesn't flatter me that well. So either a trusted friend or your phone can be one of your best assets here to take you from just being dressed to chic. So that's what I have for you today. I hope that this was helpful for you. I hope this was insightful for you. This is not about judging you, judging your choices, anything like that. But this is truly for the woman that's nodding her head right now saying, yes, this all makes sense. I am ready for that up level. I also want to always look chic. I want to look elegant. I want to look timeless and I want to have fun getting dressed. So if you want to keep hanging with me here on YouTube, make sure to check out this video next. I'll see you there.