Basically, over the past ten years, I’ve taken myself from this fashion disaster to this fashionable disaster. So I thought I’d share some tips from my fashion evolution from finding your style to feeling comfortable and confident in the clothing that you wear and how to turn fashion from something that you might kind of dread, putting an outfit together every morning, to something that you could take pride in and something that makes you really excited like it does for me!
Assess your current wardrobe
Step number one, and yes, I did break this down into steps because I am a hoe for lists. Your girl loves some good organization. So, step number one is to assess your current wardrobe. Now I want you guys to start with your own wardrobe because it can be so intimidating to, like, jump off the deep end into the Interwebs and try to figure out like, from scratch what your style is, so, I think the best place to start is looking at the clothes that you already wear and that you already love because that’s gonna give you a good hint to what you actually feel confident in.
I also feel like most of us have a couple pieces that we really love that are kind of pointing us in a direction of style, but we just haven’t brought the rest of our wardrobe around to fit those, like, a few pieces that we love, so I would suggest you guys do an experiment. For two weeks, try tracking all the clothing that you actually wear. There are a couple of ways to do this.
First of all, you could move the clothing that you’ve worn to a clothing rack if you have it. You could move it to the front of your closet. You can also turn around the hanger hook on all the clothing that you’ve worn or if you don’t do laundry that often like me, you can literally just put it in the laundry bin. Once you have this sample of clothes that you actually wear, you can start looking at what those clothes have in common.
Are they a certain fit? Do you really gravitate towards like, an a-line silhouette or a loose pair of jeans? What about the color scheme? Do you gravitate more towards pastels or do you tend to reach for your black and white clothing the most? Is there a certain brand whose quality and fit of clothing you actually find yourself wearing a lot? And lastly, something that a lot of people overlook is what is the comfort level of that clothing?
Some of us love to be comfortable and love to be able to run around, so, that is something that you should be honest with yourself with and take into consideration when you’re forming your style. I definitely grew up with the misconception that you just have to like… suffer and be incredibly uncomfortable in order to be fashionable and that’s not, like, the direct correlation.
I feel like that’s where a lot of us have a bad relationship with fashion because we’ll buy the, like, stilettos or the bodycon dress that frankly, we’re not comfortable in and then, like, beat ourselves up for not wearing it, when in reality, like you should be looking at your style from what fits your life. You shouldn’t, like, have to change to fit your clothing, y’know? *wink* So after looking at your wardrobe, you have a couple ideas of the things that you lean towards naturally and the clothing that makes you feel the best. Whether it’s a color scheme, silhouette, fabric, brand, etc.
So you’re ready to dive into the next step, which is finding inspiration. This is the fun part where you can get out your phone and your laptop and scroll through Instagram and Pinterest and old movies and old magazines and runway shows and call it research because *ZOOMS* technically it is.
Instagram and the Instagram explore page are a huge resource for trying to find your style, but before we get any further into this section, I want to say that we are looking for style inspiration, not a reason to hate ourselves and those things are sometimes a fine line on Instagram. Do I wish that I had Summer Mckeen’s face and Avery’s dog and Jesus’ abs? Don’t we all?
But, me looking at a pretty girl’s Instagram and wanting my face to look like her face is not called fashion inspiration, that’s just called hating on myself for not being born with different features. I know it can be hard sometimes but when you’re looking for fashion inspiration, try your best to separate this persona and like, the seemingly perfect life of somebody online who’s wearing it with the actual outfit and just seeing like, is that good fashion?
And would I feel confident in that outfit? That’s all that matters. So obviously, Instagram is a huge source of inspiration, both for fashion and just like, photography styles. I really like to use my explore page, but I know the explore page algorithm can be like, really weird for some people you spend three hours scrolling through memes on Instagram ONE TIME and that’s your entire feed for the next like three years. Also, just Emma Chamberlain is like, always on my explore page.
So, if you have a screwed-up explore page, I would suggest creating a new Instagram account that’s just for fashion and inspiration and you don’t look at memes on that account. Then, on your explore page, you should just get more fashion inspiration from similar accounts and then, you just have this endless resource for more fashion images that you might like. I’m gonna on the screen now a bunch of my favorite Instagram accounts for inspiration and I will also link them down below if you guys are looking for some people to follow.
You guys know I’m not a personal fan of Pinterest, but you can also look there and make your Pinterest board or whatever the kids are doing these days. I think Pinterest just skipped my generation, like, it’s a 30 year old mom thing or a thing for 17 year olds, and I’m just in the middle and Pinterest was not cool when I grew up. I was a Tumblr gal personally. Tumblr is also a great resource! Although tragically, you can no longer look at female presenting nipples, which was really my main use for Tumblr so…
Old magazines and movies are also great resources AND would you believe it, physical bookstores? If you go to the fashion section of a Barnes and Nobles, they have the coolest coffee shop books with like, collections of fashion photography. Recently, I found this book about all of the fashion designers that had been in movies and like, talking about the costume design behind them and I just like, oh, it broke my heart.
It was like my two loves were colliding. It was too much for me. So, whatever inspiration source you choose, think critically as you’re looking at each of these photos. If there’s an outfit that you’re not attracted to, before you scroll past it, think about, what do I like about that? Is this neon color a little bit too loud for me, or are these barrettes a little bit too quirky and teenager-y for me? And do I have a little bit of a mature-er style? Do I not like this gingham in her outfit and what is wrong with me??? because gingham is the BEST print. No, if you don’t like, you know, that is fine by me (or is it).
Do as you please. Ask yourself: What about your style is different from that photo that you don’t like? And the same thing for the images that you do like. Think about: Is this a really flattering fit on her? Do I like the color scheme in this photo? Those are all things that can point you in the right direction towards what your style might be. So, whatever inspiration source you choose, save up all of your photos on Instagram, you can like, create a saved folder on Pinterest, you can do a board. If you have magazines, you can cut out your victims and pin them to the wall like the fashionable serial killer you are.
Point is, you want like a mood board/collection of all of your favorite outfits so that you can zoom out beyond just one or two outfits or one little trend and see what style are you generally drawn to. At this point, It could go one of two ways. You have either found your perfect style. You are perfectly drawn all to girly twirly dresses or you were perfectly drawn towards like edgy dark colors. which might be some of you, which is incredibly lucky and then there you go. That’s your style! But for the rest of us, it’s probably gonna be a mix of things, so from there, I would suggest refining your mood board a little bit.
Go through each Individual photo that you saved or that you cut out and really ask yourself. Is this something that reflects my personality? Is this something that I could see myself wearing? Is this something that fits into my lifestyle? From there, you can zoom out again. See if it’s a little bit more cohesive. Like honestly though, you do not have to box yourself into one style. I’ve been doing this for so long, I do not have one particular style, but the mood board is more just to get an arrow pointing in a general direction. Like, do you have a little bit more of a mature style? Do you have more of a trendy style?
Do you like some bold colors and patterns and silhouettes or do you like something that’s a little bit more minimalistic? You can combine styles! Honestly, there’s where you find your own style. It’s like combining all these elements from different styles that you like and then it creates something entirely new. That’s your own, and that’s the whole point of this whole thing!
Now that you have your mood board and a sense of your style, that brings me to step number three, which is buying clothes. Ooo, this is our favorite part. Get in loser, we’re going shopping. Even though you’re probably feeling real good about your new style and you want to buy a whole new wardrobe I would recommend do not do that Impulsively buying yourself a whole new wardrobe is how you end up with a whole wardrobe of clothes you don’t want to wear like a year down the line. So I recommend choosing the five pieces on your mood board that appear the most often and that you think are the most vital to your style.
Before you go shopping, make sure you list out the five pieces, attach inspo images if you want, just so when you go shopping, you don’t get distracted by like flashy, trendy, on sale items. You are on a mission to buy the five things that you wanted from your mood board list. Once you find those perfect five items, you can take them home, wear them with your new wardrobe for a couple months, keep developing your mood board and assessing whether this new style works for you and then three months down the line, you can buy another couple pieces and keep building up your wardrobe and your new style.
Practice. Practice. Practice.
People do not think of fashion as something that you need to practice, they just think of being stylish as something that you’re born with and it is, absolutely, not. Just like you would not expect a surgeon with zero training to be able to operate on you, you shouldn’t expect yourself to have this, like, amazing, celebrity level style of fashion when you haven’t given yourself any time to practice.
Hopefully this won’t take as long as med school, but start out by giving yourself 10 to 20 minutes every morning or if you have roommates like when I was in college, I had so many roommates that I would just like, write down when they were gone and I would spend that time putting together outfits because I didn’t want other people around judging me when I was trying on like a bunch of different things.
Putting together an outfit is a process and really, the only way that you can figure out what your style is and what looks good together is through trial and error and that’s how I learned like, the majority of my sense of style is just every morning waking up putting together an outfit, realizing that it doesn’t look like how it looked in my head and it’s absolutely hideous, and then slowly switching out pieces, trying on a new pair of shoes, adding a belt, changing out my earrings, adding a new jacket, until the outfit looks balanced and it looks good. Related to that, make sure you give yourself adequate time to shop.
Spending more time shopping does not mean that you buy more clothing, it means that you’re giving yourself extra time to find the perfect piece of clothing. I was like a very weird shopper growing up and I really still am. I would go to the mall for like 4 hours, try on tons of outfits. I was SO annoying to all of the fitting room employees, they’re like, “when’s she gonna buy something?”
I would spend so long at the mall, going through all of these stores, trying on all of this clothing and I would usually not buy a single thing. BUT it really helped me develop my sense of style because I knew from trying on all of these new pieces of clothing what I liked, what fit me, and then when I did make a purchase, it was thoroughly informed like, your girl did her research!
Not giving yourself enough time to shop is also a huge reason that we end up with shit that we don’t like in our wardrobes because we like, bought it on impulse in a sale or we didn’t really take the time to think about it. So unfortunately, I don’t have like, a definite conclusion to this. There’s no point that you’re gonna reach where you’re like AHA! I found my style! It really is a process, and even I am still deeply in the process of trying to find my own style but over months and years as you continue to exercise your critical eye for outfits to really think about what suits you and what doesn’t. You’re gonna develop your own unique sense of style and I don’t know! That’s so exciting!!! That was really geeky, sorry, I get excited about fashion sometimes
So many of us have a really cool, adventurous sense of style. We have these outfits in our heads that we wish that we could wear, but we just don’t feel confident enough to. It’ll sound stupid to a lot of people, but I’m here to tell you that wearing an outfit that you love and changing up your style is something that is scary and it’s something that takes courage in a very specific way.
Putting effort into an outfit is a way of going out into the world kind of vulnerable because these days, it’s so cool to not care and to not put effort into anything, but dressing your best is a way of saying Hey! I woke up and I cared today! I cared so much and I put together this really cool outfit and please just don’t insult me about it. That was why I was so scared to express my style in high school for a while everybody from my dad, to my calc teacher, to my classmates would comment about my outfits. Even like, compliments and well-meaning comments can… kind of hurt when you’re like, experimenting with something.
Like, when you wear dress for the first time and then your mom’s like, “Oh,” like, “somebody’s dressing up today.” Yes! I am! I am! I changed, okay! It’s hard to change sometimes, and you should be proud of me for that! So anyways, if you guys are scared to wear what you actually want to wear, I like, completely feel you, but I also wanted to give you guys some of my tips for how I overcame that over the years.
So, my first tip is to ease yourself into your new style piece-by-piece. Sometimes, people just take a while to adjust to change but eventually their image of you is gonna catch up with your image of yourself. For me, it took like a year of dressing up for people to realize like, “Oh, that’s just Ashley now. She just likes fashion.” By senior year, I could pretty much wear like, anything. I could wear heels, I could wear a dress, like, I could be the most extra person ever and people were just like, ”
I started out by wearing these little booties that were like three inches tall on the heel, and they went by a little bit less noticed because they were like boots and they weren’t open toe heels and then gradually, I like, worked my way up to a little bit of a higher heel and a little bit of a fancier shoe. Even though probably nobody cared that much, like, that was my way of slowly introducing the heels into my wardrobe My next suggestion, especially if you aren’t surrounded by people who really love and appreciate fashion, is to make your own little space to enjoy it.
That’s honestly how I got started on like, my whole YouTube journey was really just that I wanted a space to geek out about fashion and to show off my outfits because I didn’t feel like I had that outlet with my family and friends and now it’s honestly easier than ever. You can start a blog, if anybody still does that. You can make your own Tumblr page, you can make your own Instagram or your own Youtube.
Especially if you’re surrounded by people who don’t really appreciate your style it can really boost your confidence to find a place online where even just a couple people are appreciating the outfits that you put together. 00:13:35,000 And my last tip is that fashion is so subjective, and just because somebody doesn’t like your outfit, does not mean that it’s not a damn good outfit. *sassy finger action* You know who never gets roasted on their outfits? Jimmy Fallon. You know who always gets roasted on their outfits? Lady Gaga. Who is the fashion icon? It’s Lady Gaga. Sometimes, it can be hard to put yourself out there with fashion, because you know if you wear like, a hoodie, nobody’s ever gonna make a comment about it.