44 Style Rules & Tips from 15 Years in the Fashion Industry

This is Anna. She just turned 44 this month. She has worked in the clothing and fashion industry for over 15 years and wanted to share some style rules she has learned along the way. Okay, I'm poking fun at being 44 a little bit, but to be honest, I am actually happier than I ever have been. I've been, um... at 44 than i was at any other age but anyway i hope you enjoyed a little humor i realized recently that i have been working in the fashion industry in one way or another for over 15 years so i thought for my 44th year on this planet i would do a video of 44 Style tips, summer style rules that I think everyone should learn and that I've learned myself just being on YouTube, being a boutique owner. I even went to Parsons in New York City. So I've just been in the fashion industry for a while and just learned a lot of things, especially with my time here on YouTube. So I want to make this video in a quick, snappy, snippy, like, you know, not much explanation kind of form and let's get started. If your outfit feels boring and basic, just try throwing a sweater over your shoulders. Instant upgrade. Also, if your outfit feels boring and uninteresting, add a really fun or cool handbag. Same outfit, it feels boring and uninspired, not interesting, add a really cool belt. However, do not add all three of these. That might end up being too much. It might look like a big frazzled mess. One, maybe two, is usually all you need. Stop caring about being overdressed. Focus more on wearing whatever is going to make you feel like your best self and the most confident that you can be. If you've never tried picking out your outfit the night before instead of the morning of, try it for like a week and it will probably change your life. If you have a larger bust, a tighter fitting, Crew neck, high neck shirt is going to emphasize your bust. If you want to de-emphasize your bust, if you wear a V-neck, it's going to bring all the attention up to your neck and your face. You know those fabric belts that come with a lot of dresses and a lot of shorts and a lot of pants? If you just take that belt off and put your own beautiful leather belt with it, it's going to look... A lot better, a lot more stylish, and a little more expensive. If your outfit is more relaxed and more undone and more effortless and flowy, try adding a structured bag to give it a little more intention. Matching your shoes to your bag looks cute and coordinated and like a look, but matching your shoes to your bag, to your earrings, and then your necklace, it can start to look a little bit dowdy and outdated, so the rule of thumb is two is great, three gets hate. I just made that up. I don't like that though. Let's see. Two is great. Three is too much. Anyway, moving on. Most of the time you're going to get what you pay for. And if you buy a $10 sweater, It's very likely that after about two or three washes, it's not gonna look that great, or it's gonna be stretched out and you might have to throw it away. Whereas you could buy a $100 sweater, but it lasts for years and years and you get hundreds of wear out of it. That's not always the case, but a lot of times it is. Now on the flip side, these bags that are like $10,000, I guarantee you they're not that much better quality than a lot of these handbags that are under 500. The ones that are between three and 500 have much the same quality in a lot of cases. There really isn't that much difference aside from that logo that's on it. And so those extra thousands of dollars that you're paying for that bag is, it's really for that logo. I'm not saying don't do it. I love some designer bags and I have a couple, but I am honest with myself about what I'm actually paying for. A tight, very fitted outfit is not going to make you look skinnier. In fact, it can do the opposite. A very tight, ill-fitting outfit that's just like, you know, all the way, it can kind of make you look a little bigger than you actually are. However, the over, super oversized, if you're trying to hide something, it often doesn't really, it hides everything, but it also just adds. Bulk, and it can make you also look bigger than you actually are. So the winning formula here is something either body skimming or relaxed or a little loose fit, but not super tight and not super oversized. And there is ways to wear both of these things, but they do take a certain styled balance and you have to work with your proportions. A lot of clothing that doesn't fit you quite right and it just kind of feels kind of does it kind of hangs improperly can really be fixed and made absolutely amazing with a $15 tailoring tweak. However, when it comes to buying clothes, you want to make sure it does fit you the way you want it to and the shoulders because that is the hardest part to tailor Unless you have a really good eye for color and you're really good at mixing and matching colors, your best bet and you're going to have a more cohesive closet if you stick to mostly neutrals in your closet. Notice I did not say all neutrals, but most of your closet are neutrals that you like to work with. You're going to find much more outfits within your clothes with neutrals. Steam and iron your clothes. Make sure that you don't run out the door with wrinkled clothing on. Not only does it look like you just pulled your clothes out of a pile on the floor, it also can give a kind of a sloppy first impression. Fit is really everything. If something is $1,000, but it's too tight and it's pulling and pinching and everything else, it's not gonna look as good as the $20 item that actually fits you really well. Back to a previous point, I would get things tailored if they aren't fitting you quite right, but you really love them. Fashion trends will change and I don't think they change as fast as people think they do but they do change and if you like trends and you like buying into some trends just know that every few years that item is probably not going to be in style anymore. So nothing wrong with buying trends. I love trends. Lots of people love trends but just know that Whenever you start with trends, eventually that thing will become dated. And I think that's where a lot of women get in trouble is they get into trends in their twenties and then by 35, they're just not into trends anymore, but they're still wearing the trends that they wore when they were 25. And then they start looking a little bit outdated. Editing my closet every season has changed my life. If you do nothing else in this entire world of fashion, just edit your closet and have only the things in there. That work for you and fit you right now that you can wear right now. It will change your life. If you're shopping and you see something that looks kind of cool, ask yourself, would I wear this tomorrow? Could I wear this tomorrow? And if the answer is no, you probably don't need to buy it. Beware of sales and buying things just because they are cheap. If you buy it just because it's cheap and just because it's a good deal. But you're never going to wear it. It's still kind of a bad purchase. The thrill will be gone once you get home with that cheap item, and then it will just sit in your closet forever, taking up space. Stop saving all your special items, all your very nice items, the special items that have meaning and you keep in a box where they're safe in your closet because you don't want to mess them up. Stop doing that. They are not meant to sit in a box. They're meant to be worn. Wear them, love them, use them. And in fact, a lot of these items that you find really special and you love a lot are the thing that's going to really give you a lot of personality in your clothing and a lot of personal style. If you take a picture of yourself in your outfits every single day, and then you put them in a folder on your phone, you're going to have an online catalog of everything you have in your closet. And then of course, if you go back in a year and you only have, you're only wearing the same 10 items in 19 different ways, then you can kind of tell what you might not need in your closet anymore. If you only ever buy one coat, you want one coat in your life, and that is all you want, like, Say you live in Florida and you don't need a lot of coats, buy a long coat. The long coat looks beautiful over evening wear, over dresses, over casual wear. It even elevates your casual outfits. It really just goes with so many things and it makes a beautiful first impression. I love the short jackets. I love the crop jackets and everything, but they're not quite as versatile. A trench coat is really good here, but it doesn't have to be a trench. Buy for your real life, your real life right now, not your fantasy life. I love the fantasy life, and my fantasy life, I get swept off to all kinds of fancy, beautiful, wonderful vacations. But in real life, I got to go pick up my kid in a little bit, and he's probably going to want to play outside in the hot, sweltering heat and ride his bike. So in a lot of days, I need to dress for that, not being swept off to the Greek islands. on a yacht although i would i would love that i would love it but that's just not my real life right now your closet should generally match what you spend most of your time doing you are not investing when you buy clothes maybe the one Chanel bag that's going to be worth something more someday but any other items you're not investing when you buy fashion you're investing when you invest into a 401k or a Roth IRA or index funds and you are investing for retirement or something like that those things can actually make you money in the long run. Now buying clothes that you love and feel amazing in is an investment in yourself and so I think that should be the key takeaway here is to invest in yourself and not only is that clothes that make you feel good but that's doing things for yourself and saying no when you need to and giving yourself space and giving yourself time to breathe and think and be you. That is an investment in yourself. But fashion in and of itself, an expensive coat is not an investment. That's just a beautiful coat and it's probably a great purchase, but let's not kid ourselves and call it an investment. Just because something is trending does not mean that you need to have it. In fact, a lot of trends, if you really look at them, they might not be for you. A lot of them aren't for me. It's more beneficial to spend time I'm figuring out what styles. work best on your body, what you feel comfortable in, what you really love to wear, and then you can look at these trends through the lens of your own personal style. Personal style takes time. It's not something you can figure out in one day. If you want to be the person that has, that you can get ready in just five minutes and look fabulous, you have to do a lot of work on the back end. You have Figure out what works for you. Really take some time, just spend time on yourself to figure out how you wanna show up in the world. Build a closet over time that represents how you wanna show up in the world and eventually you will get there and it's totally worth it, but it does not happen in a one day. If you focus on textures and fabric and styles in your closet rather than prints, your wardrobe will feel more timeless and chic. Now prints are not the enemy and nothing wrong with prints and I have a few prints, but when your closet is full of prints, You can often find... find that you go to your closet and nothing really goes with each other and you have a closet full of clothes and nothing to wear. Y'all, don't buy shoes that are uncomfortable and then expect that you're going to wear them more than once because you won't. You wear them one time, you get blisters, and you will never want to put those things on ever again. Don't buy clothing that's uncomfortable or itchy or that you have to fidget with or have a skinny day or only be standing like this in order for it to look good and feel comfortable. If any of those things happen, you're going to wear it once and then you're never going to wear it again. Your posture is part of your outfit. I've had to work on this my whole life, but it's a very easy and free thing to do and to work on to look better in your clothes. If I know that I'm going to be walking a lot or I'm going to be on my feet all day, I pick out my shoes first and I build my outfit from there. It just eliminates a lot of things in my closet and makes it easier to get dressed. You can make more use out of the clothes that you currently have by mixing three Formal with casual. I think a silk blouse, a beautiful silk blouse always looks beautiful with a pair of blue jeans. When in doubt, dress it up. Dress up a little bit more than you think you should. You're never gonna be embarrassed by being the best dressed person in the room, but if you're the worst dressed or you look like underdressed, you. you're not going to feel that confident. It's not the end of the world if you wear an outfit that later you deem to be a fashion fail. In fact, all of the most stylish women out there have many fashion fails and that is how they have ended up honing in on their own personal style. Plus, I feel like it could make a great story. it is okay and actually very on trend in 2025 to mix gold and silver together. most every stylish woman i've ever met and ever known has somewhat of an organized closet. maybe it doesn't look pinterest ready but they generally have some kind of rhyme or reason to their closet. if you have not edited your closet, if you have not organized your closet in a while but you want a new wardrobe, you want a new style, Your closet is a really good place to start. Speaking of closets, more times than not, having less clothes can actually lead to more outfits. When I got rid of a lot of my clothes a few years ago, and I mean, I was in the situation where I could barely even get any space in between my clothes. I had so many crammed in there. When I got rid of everything that just was not working for me right now, was like too small, just had to wear high heels, five inch heels to wear and all of this stuff. And I just Did something else with it and I got it out of my closet. It just made getting dressed so much easier. Replace your bras at least once a year if you can. Do I replace mine once a year? I try. I try. Okay. And have I found really wonderful bras out there? I haven't. But you really are supposed to replace your bras probably a lot more often than we actually do. And not Not having a good supportive bra can often lead to your clothes Leave your clothes not looking as good on you as they could. And sometimes they can even make us look a little older than we are. So good bra, good undergarments are important with getting dressed. Your style will probably always evolve. What you love now and what works for you now might not work in 10 or 15 years. And that is totally okay. Our life changes, our circumstances change. And so our style can evolve as well. And my last style tip, number 44 of my... Birthday style tip extravaganza is to not discount how important dressing and getting yourself dressed and fashion is in your life. Not fashion necessarily, but putting yourself together and spending time on yourself and putting in the effort to just look good and look the best you can. It isn't frivolous. It isn't selfish. It's actually very important to how you show up in the world. You're not going to show up as the best mom or employee or a boss or anybody if you don't put some time and energy into yourself. Prioritizing yourself and your own happiness and and how you like to feel is extremely important and will make you show up better in every other aspect of your life. So anyway I hope you liked this. It was like you know I was trying to go fast and um just to the point. In my head this seemed like a fun video. Let's see how it works out. I know I've said a lot of these before, but sometimes it's fun just to hear them again and just like in a little reminder way. So I hope you like this video. You'll have to let me know if you're new here and you made it till the end. Oh my goodness. Hi. You can subscribe down here in the bottom and um So yeah, let me know what you think. I hope these were helpful and I will see you next time.