My Best and Worst Outfits Over the Years


Five years ago today, I hit publish on my first blog post ever… Crazy how time flies, right? It’s hard to believe what a big part of my life fashion blogging has become ever since I decided to start Graceful Rags in the summer after my sophomore year of high school. From thousands of photos, to 597 blog posts, to lots and lots of tears, it’s been a time and a half—that’s for sure. One of my favorite fashion bloggers Lee from LegalLee Blonde published a post a few months back where she shared her favorite and least favorite outfits from every year of blogging, and I thought that would be the perfect thing to post on my five year ‘blogiversary’. I’m really putting myself out there today because some of these outfits are cringey as heck—I hope you at least get some entertainment off my embarrassment. So without further ado, here are my best and worst outfits since 2016!

Worst Outfit from 2016

First off, can we just comment on that major baby face? I was 16 when this photo was taken and I look like I’m 12—at most. I never really thought my looks have changed that much over the years, but my old blog photos proved me wrong.

The first unfortunate thing about this outfit is the capri length of these baby pink pants. I don’t have a problem with colored jeans (and thanks to TikTok, they’re back on trend at the moment), but these pink pants are particularly unflattering. It could be partly the angle, but I look like an Oompa Loompa in this photo.

Next up, this camo top. I like camo print, but I do think it has a time and a place—and pink pants with a sparkly necklace and sparkly espadrilles is not it. Overall, not a horrible outfit, but it’s not cute, either. You can read the rest of the post and my cringeworthy writing here. I’ve always been a dork, but boy, these old blog posts put me on a whole other level. The dad jokes are just too much, even for me. Why were people friends with me in high school? Lol.

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Best Outfit from 2016

I still think this combo—a red flannel, beige sweater, black pants, and booties—is a cute fall outfit, and I’ve worn it several times in the years since this pic was taken. I would probably swap out the dark brown boots for a taupe color, to better tie in with the sweater, and I would pick a different purse. But otherwise, I still have all these pieces and would rock the outfit again. You can check out the full blog post here.

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Worst Outfit from 2017

This outfit is absolutely atrocious. I can’t believe I ever thought this look was even remotely cute. In fact, this outfit makes me seriously question my sense of style. Am I actually stylish, or do I just like clothes? Because I do think there’s a difference. For one, these jeans don’t fit me at all; they have a saggy crotch and are caught somewhere in the unflattering middle between skinny jeans and a straight-leg fit. The yellow purse is a completely random pop of color. Also, tucking this floral tee into my lower-rise jeans is a great way to make me look like I have a belly when I don’t. And last—but certainly not least—this Addidas striped jacket over the top? Why??? If you want to see more of this ugly outfit, check out the whole post here.

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Best Outfit from 2017

While not the best photos, I would wear this outfit again in a heartbeat. I love the color combo of burgundy, taupe, and crème for fall. I also think this plaid wool skirt is super cute and pairs perfectly with my big blanket scarf. Maybe this look seems really dated, but as I’ve established several times before, I’ve never been very trendy. Plaid skirts and blanket scarfs forever and ever. See more of the look here!

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Worst Outfit from 2018

Sifting through all my blog posts today was a good reflection exercise. It is nice to see that I’ve grown over the years—my writing has become more mature, my fashion choices are better, my photos are generally lighter and *slightly* improved. But one thing that I’m still not good at? Posing. This photo is a perfect example of an extremely cringey stance—awkward arm angle, scrunched shoulders… (You may remember my post Why I Could Never Be a Model). I like to think my blog posts have slightly better posing now, but that’s because I take a million photos before my stance is just right. I don’t think posing will ever come naturally to me.

Now, the outfit. These shorts are low-waisted and too big in the waist. As I established when discussing my worst outfit from 2017, tucking any top into low-waisted bottoms is a sure-fire why to make yourself look like you have a belly pooch. The purse is a weird pairing with the outfit, and I’m definitely too old for hair flowers. And lastly, the color combo and accessories together are so tacky. I love a good patriotic outfit for the 4th of July, but sometimes the red, white, and blue look too ‘forced’ together—case in point. You can find the original blog post here.

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Best Outfit from 2018

This outfit may not be the trendiness or something that most girls my age would gravitate towards, but I love the old-fashioned vibes. The crème lace blouse and olive midi skirt pair perfectly together, and the pleather military style jacket is a fun addition. I also think my light green clutch, which is truly vintage from my grandma, is the perfect accent color to the olive green. I would love to wear this outfit again and would probably only change the shoes—I think heels would be more flattering with the longer skirt. You can see more of this outfit in this post.

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Worst Outfit from 2019

blue and white bodysuit, tuxedo striped jeans, striped heels

Even the thought of this outfit makes me gag. It is SO unflattering. Ghastly, really. I remember wearing this in downtown Denver with my friend on our ‘night out’, and I’m mortified at the thought of wearing this in public (let alone that it’s on the internet). I didn’t have a proper bra to wear with this blue and white bodysuit, and I somehow convinced myself that it was okay to go braless in it. WRONG. This top is low-cut to begin with, so I was hunching over and pulling it up all night, worried about a nip-slip. There is also unflattering side boob/armpit flub on full display in this bodysuit. And, yet again, I tucked it into low-waisted jeans. I have since vowed never to wear a bodysuit unless it is with high-waisted bottoms. I do like the color scheme of this outfit and the striped navy heels, but the braless-ness really kills it. I should try recreating this look with updated pieces—a white lacy bralette underneath and high-waisted blue denim. Maybe then I could redeem myself? Here’s the original post (barf).

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Best Outfit from 2019

pastel blue, pattern mixing, white shoes, botanic gardens

I think this outfit is so stinking cute! This is one of my favorite tops to begin with (it’s pinstripes AND polka dots so the pattern mixing is built in), and wearing it tied with this blue bedazzled skirt was a chic way to do monochrome. And of course, I can never go wrong with my white studded mules. I don’t know what I wore before I got these. See more of these fun botanical garden photos here!

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Worst Outfit from 2020


Thankfully, finding the worst outfit got harder as the blogging years went on. (But in the first few years, there were a lot of bad looks to choose from.) My point being that this palm print top and black shorts combo isn’t horrible, like some of the others, but I wouldn’t wear it again. The black is a little too harsh for this playful top, and my biggest problem with this outfit is the fit. These shorts are too big in the waist and they’re low-waisted (are you noticing a theme?). Since my shirt is pretty cropped, this meant you could see my clashing belt and an awkward strip of stomach. Plus, in hindsight, I really don’t like these photos, so that also sways my opinion of this outfit. You can see more pics here (at least my necklace layering and hair are cute).

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Best Outfit from 2020

Jane Sloan style, the bold type, freeform

This look is from my Binge Worthy Fashion series, when I dressed up as Jane Sloan from the TV show “The Bold Type”. I feel like such a badass in this outfit. The dark lip, the slicked back low bun, the statement sleeves, and most of all, the clip-on dangly hoop earrings. Simply put, this outfit has a lot of drama, and I’m all for it. I would love to actually wear this look out somewhere, since I photographed it during quarantine and didn’t have anywhere to go but my bedroom. I think when I do eventually wear it, I’ll pair it with a cooler purse for added pizazz—maybe something silver or colorful. See more of the outfit here!

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Worst Outfit from 2021


There’s nothing fundamentally wrong with this outfit. I like the Carrie Bradshaw vibes of the pink furry skirt (which is actually a scarf) and the silver accessories. However, I don’t think this outfit is particularly flattering on me. Something about the bright pink color on my bottom half and the peplum top made me look SO hippy—as in, having wide hips. I’m all for a good hourglass look, but I don’t know… something about this outfit made me feel very wide in the worst kind of way. But again, the concept of the look is cute! You can hear more about how I styled this tube scarf as a skirt in this blog post.

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Best Outfit from 2021


This might be my all-time favorite outfit from the blog. Not only did the pictures turn out well, but I felt SO cool and stylish in this look. The leather shorts felt more ‘high-end’ than what I usually wear, and the star-print tights were the perfect accessory. The color scheme was on point, too! I just love everything about this outfit. You can check out the original blog post here.

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So there you have it. My favorite and least favorite outfits from over the years… ’cause if you can’t make fun of yourself, then you’re doing something wrong—right? It’s hard to believe it’s already been five years of Graceful Rags; it really does feel like a part of me, and as many times as I have considered quitting blogging, it’s hard to imagine life without it. Probably would have a lot more free time, though, lol. You can check out last year’s blogiversary post here, where I talked about the best and worst parts of fashion blogging. Whether you’ve been there from the beginning or are a more recent follower, thank you SO much for all your support! I have met some really cool people and had some awesome experiences because of my fashion blog, and I’m so grateful for that.

I hope you have a great start to your week.



10 comments on “My Best and Worst Outfits Over the Years”

  1. This is such a fun post and reading your critique was really interesting. I definitely agree with the low waisted vs high waisted bottoms with certain outfits: it can make a difference in look and fit. I really love your favorites and your pink scarf skirt outfit is really cute to be but I think hips are not a bad thing lol!

  2. Such a fun post, Grace. I love your ‘Best 2021 outfit’ it’s so well put together! Whenever I flip trough my photos from decades ago, I find many that makes me cringe and think – What was I thinking with that outfit? But then again sometimes I choose outfits based on how they make me feel

    1. Thank you Aiva! I’m glad you enjoyed the post. It’s fun reminiscing and laughing at ourselves, isn’t it? Haha.

  3. Happy Blog Anniversary, Grace! This was super fun to read. I agree completely with this statement…”’cause if you can’t make fun of yourself, then you’re doing something wrong”! That is so true. But that being said, we are our own worst critics and I think that your cringey outfits are not nearly as cringey to the rest of us! But I hear you, girl! I have some pretty cringey outfits and articles out there in internetland, too!


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