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The 30 Day Outfit Challenge

Updated: Apr 30, 2021



You know that TikTok trend where people show off all the outfits they never got to wear in 2020? While I haven't exactly hopped on that trend, I have plenty of those outfits myself. Seriously, some of my cutest outfits are just sitting to waste in my closet. Why? Because I thought I needed a special occasion to wear them, but after binge-watching videos on #FashionTikTok I was reminded that I don't. With an idea from my sister, I have challenged myself to wear a new outfit every day for the next month which I'm uncreatively calling The 30 Day Outfit Challenge.


Of course any challenge comes with a few rules;

  • You can repeat pieces, but not full outfits within these 30 days. (No 8th graduation, outfit repeating Lizzie McGuire's here!)

  • Do your best to fit the brief. I did buy a few extra pieces for this, but most come from what I already have. Don't feel pressured to buy anything.

  • Have fun! This is simply an excuse to dress up after all!

Now, I present the outfits. This will be updated daily with a picture of what I wore, and brief description, so stay tuned!


1. Your Best Influencer 'Fit- We're talking the outfit that will give you all the likes on the 'Gram.

Because satin = all the likes.

I've seen satin dresses and two pieces all over my Instagram feed! I love this two piece set because of its gorgeous blue color and shape. Not sure how many like this photo would get, but at least I look good!


2. An Animal Print Outfit- Leopard, Snakeskin, and Zebra! Oh my! the possibilities are endless.

These pants were a need. I still don't know what for though.

I don't know where I was planning on wearing these snakeskin pants when I first bought them almost a year ago, but an animal print themed day was the perfect excuse to break them out!


3. Dress Like Your Sibling- Or someone you consider to be a sibling! Also, this is a great excuse to steal (oh, wait, I mean borrow) from your sister's closet.

My sister is probably not getting this shirt back.

My sister I am are basically polar opposites. I have a more girly, glam sense of style, and she has a more laid-back, cool style. However, I truly admire her style, so I borrowed her oversized Beatles shirt and fun red glasses. She definitely would have pulled this off, but than me, but it was fun to wear it!


4. Your Easter Dress- It's Easter Sunday after all. Let's see that Sunday best!

The Easter Bunny could never.

One of my favorite Easter traditions is picking out my Easter dress. This year I went with a blue, floral maxi dress with a tie-back, and a ruffle strap. For sure, I was feeling blessed and rocking my Sunday best! Happy Easter!


5. A 60's Inspired Outfit- This was such an amazing time for fashion. You can wear mod, hippie, or even a sophisticated French style.

A simple black shift dress for the win.

For my 60's 'fit I wanted to do an elegant look with my outfit, but really play around with the hair and makeup. I went simple with a black shift dress that my grandma assured me she would have worn in the 60's. I accessorized with a pearl necklace, and black pumps with a bit of sparkle. I did a fun poof with my hair and did Twiggy's iconic lashes for my makeup. I truly felt like a refined 60's icon with my look!


6. A 70's Inspired Outfit- It's time to break out the bell bottoms!


That 70's Show, but make it fashion.

Like I said, bell bottoms for the win! I paired them with a cute, fitted striped top, brown boots, and a matching belt. I curled my hair and parted it down the middle, and used warm tones for my makeup look. I truly think it's a look that Jackie from That 70's Show would approve of!


7. Dress Like Your Favorite Disney Princess- This is really just an excuse to wear stunning shoes and a tiara

I guess it's pretty obvious what princess I chose.

Okay, so I didn't wear a tiara, but neither does Cinderella when she goes to the ball. To channel my forever favorite princess I choose a lace blue dress with puff sleeves, glittery silver pumps, and accessorized with a pearl headband. Now if you'll excuse me, I'm off to find my Prince Charming!


8. A Grunge Look- The 90's are back.

It's not a phase mom.

When I put on this outfit I felt like I had transformed, just for a moment, into the person I was meant to be, so don't be surprised when I'm hitting up every rock concert post-Covid. For my grunge look I rocked a Rolling Stones tee, and red flannel, leather shorts, black tights, combat boots, and a couple of black chokers.


9. An Early 2000's Mean Girl Outfit- Channel your inner Karen Smith, Gretchen Wieners, or Regina George

So fetch!

Obviously, I was going for the Queen B herself, Regina George. In typical 2000's fashion, I wore a Juicy Couture jacket, a fitted pink tank, a mini skirt, and some black pumps. I finished off the look with an initial necklace and Regina's signature straight side part. Now don't let the look fool you, the only Mean Girls energy I'll be channeling in 2021 is the the fashion.


10. An Outfit for Going Out- Time to break out that outfit you've been saving for the first night out post-Covid.


What? You don't get dressed up to lounge around at home?

I'll admit, for a night out I don't usually go with a sequin romper, but after a year of being stuck inside I plan to be dressed to the nines on my first night out. This wine colored sequin romper is fun and flirty and perfect for dancing the night away!


11. A Cute Workout Set- Don't worry this doesn't mean you have to go to the gym.


*cue Werk Out by Todrick Hall

Working out is actually fun when you look this fierce. For my 'fit, I chose this cute two-piece leopard set from Fabletics and paired it with leopard adidas sneakers. I truly felt like I could accomplish anything. Now let's ignore the fact that no workout followed putting this outfit on.


12. Dark Academia- Think Gossip Girl, but darker.

Cause everyone reads standing like this.

As someone who is obsessed with Gossip Girl, I've been looking forward to this day. For my dark academia look, I did a white button down with a plaid skirt, black tights, heeled combat boots, and a black jacket.


13. Your Zodiac Sign- Interpret this how you want. As a Virgo, I'm using it as an excuse to dress like a Goddess.

In case you didn't know, Virgo is the goddess of purity which I interpreted as an excuse to wear my cutest gold romper. I matched the romper with some strappy champagne heels, and, in typical Virgo fashion, I felt ready to conquer the world!

14. Front Row at Fashion Week- This brief is nothing more then me trying to manifest being back at Fashion Week soon.

The only question is am I dressed for New York, London, Milan or Paris?

If you were to ask me what I miss most about my life in NYC, it would be Fashion Week. Although, I want to produce the shows rather than be front row, I still imagine how I would dress all the time. Blazers are one of my favorite reoccurring Fashion Week trends because they're so chic and timeless. I paired mine with some black tights and my favorite Steve Madden booties to complete this front row worthy look!


15. Your Favorite Celebrity (Past)- If you know me, you know exactly who's style I'll be channeling for this look.

I know. No one is surprised by my choice.

No surprise here. I dressed up like my queen, Audrey Hepburn, in her most iconic role of Holly Golightly. This meant a sleek lack dress, pearls, sunglasses, and, my favorite accessory, a tiara. Sadly no Tiffany's box or cat without a name was included in this look.


16. Your Favorite Celebrity (Present)- You'll probably also know who I plan on channeling here.

If you guessed Blake Lively then you were correct.

Who could forget that time Blake Lively wore all those fabulous suits to promote A Simple Favor? Definetley not me! I decided to channel that look with a white pinstripe blazer suit, a black tank, black booties, and, of course, a red lip. I just hope it would make Blake proud.

17. A Monochrome 'Fit- Head to toe in one color. But what color will you choose?

I chose head to toe pink!

I love a chic monochrome set, and ha been saving this one in my closet for a rooftop brunch in NYC. While I'm hoping that day will come soon, I decided my outfit challenge was a great enough occasion to finally paired. I paired the pale pink set with bedazzled pink heels and cute dangling earrings to complete the look.


18. A Vintage Outfit- I mean all pieces MUST be purchased at a thrift store or vintage shop. Let's see what we can find!

Am I using this challenge as an excuse to wear these booties as much as possible? Yes!

Okay, so, this outfit isn't exactly thrifted, but each piece is secondhand. I found the sleek, pink blazer at a thrift shop, ordered the chic, blue shorts at a thrift shop, and my sister gave me her old white tank. The shoes technically aren't secondhand, however, I've worn them so much, the might as well be!


19. Your Cutest LBD- Cause everyone needs at least one. Let's ignore the fact that I have like 15.

Seriously, one of my favorite wardrobe staples!

Name a look more classic or elegant than the Little Black Dress. You probably can't! When it came time to decide which LBD to wear the choice was hard. I have too many. I ultimately decided on this lace one that I wore to my first New York Fashion Week party, since that holds a special place in my heart and on my Instagram feed.


20. Dress for the Job you Want- I mean the dream job.

The perfect excuse to break out one of my Fashion Week jumpsuits!

Most of you know by now that my dream job is to be a fashion show producer. While you might think this calls for my most glamourous outfit, this is not the case. Typically, working a Fashion Show means whipping out all black attire. I, personally, love to wear jumpsuits because they're put together and classic. The jumpsuit I chose also made it on to The Real Housewives of Beverly Hills, so obviously it's a good one!

21. Dress Like a Tourist- No ugly tee and socks with sandals here. I'm talking your most fashion forward tourist look and for anywhere you plan on traveling.

Considering I live in Florida, I could have gone to the beach for this photo, but I decided the palm tree in my front yard was just fine.

So, I was going to to do a more cosmopolitan take on this brief, and dress how I would if I was in London or Paris, but then I found this palm leaf romper in my closet, and decided it ,must be worn. I paired it with some chunky espadrilles and sunglasses to complete my tropical look. I hope one day soon I can travel in this outfit!

22. Earth Tones for Earth Day- Bonus points if the outfit is sustainable.

It just feels right to wear green on Earth Day!

For Earth Day, I decided to wear green sweat pants, and a charcoal bodysuit to match tones found in nature. I also believe this cute set from Fabletics is eco-conscious. (At least, I'm pretty sure. Please, don't quote me on it.)


23. A Spice Girls Outfit- But will I be Scary, Sporty, Ginger, Posh, or Baby?

Spice up your life!

You all probably thought I was going to be Posh, but I went with Baby. This was mostly because I look most like her and love a pink dress moment. I finished off the look with white sneakers and her signature pigtails. I've spent the rest of the day with "Wannabee" playing on repeat in my head, but I'm not mad about it.

24. Jeans and a Nice Top- I mean, it's the go-to.

It's anything, but basic.

Jeans and a nice top is quite literally the most generic outfit combination. However, there are so many ways to play around with it! I chose a hot pink corset top, distressed straight leg jeans, and finished off the look with some fabulous pink shoes. Seriously, I can even find a way to make jeans and a nice top #extra.

25. An Outfit for Shopping in Soho- Time to channel your inner New Yorker. My guess is she's chic and wearing black.

I wish this was Soho!

The amazing thing I learned while working in Soho is that in the city, you can wear anything you want as long as you have the confidence to do so! However, I did choose the an embody a typical chic, all-black look. You just can't go wrong! I paired my jumpsuit with snakeskin heels, a high ponytail, and a bold red lip, and I was back to feeling like a fabulous New Yorker!


26. An Outfit for Dining on Melrose Avenue- Be the LA cool girl, you've always dreamed of being.

"So do I call LA, or does LA call me?"

When I think of LA fashion, I think of flirty and trendy styles. I'm not too sure that this look is fully LA, but, lately, I've been loving the many ways that influencers have been turning scarfs into tops, so I decided to hop on that trend. I was able to transform my $10 scarf from Amazon into a flirty top using nothing but a gold chain necklace, and a safety pin. After throwing on some sunglasses I was ready for LA to call.


27. Your Best Street Style Outfit- What will you be wearing when the paparazzi snap your street style photos?

Please pretend that this photo was taken in the streets in NYC.

For this look, I decided to go with an outfit I wore to a street style event for NYFW. I made a fun pair of joggers look more glam with a fun asymmetrical top, but kept it casual with a pair of sneakers.


28. Your Favorite Movie Character- What would your favorite movie character be wearing in 2021?

"The rules of hair care are simple and finite. Any Cosmo girl would have known." -Elle Woods

I've loved Elle Woods since I was a young girl! In Legally Blonde, she proved that any woman can be both fun and girly but still have a brain. With this look I show that I mean business by choosing a blazer set, but keep it fun and true to Elle by choosing a hot pink color!


29. Your Favorite TV Character-Who's your tv style icon?

"A little bonjour goes a long way!"

I'm sure many of you thought I was going to choose Serena van der Woodsen or Carrie Bradshaw, but I went with Emily from Emily in Paris. I was obsessed (and I mean OBSESSED) with her check blazer set and red beret outfit, so much so that I was constantly searching for dupes on the internet. (We can't all afford Amanda Uprichard!) When I finally found the perfect set on ASOS I just had to buy it, and this brief gave me the perfect excuse to finally wear it!


30. An #Extra AF Outfit- I'm talking the most extravagant thing you have in your closet! Like seriously break out that old formal dress or pull out a ball gown!

Would you have expected anything less from me?

Of course I threw on an old formal gown and went full glam for the last day of this challenge! I accessorized with rhinestone earring, a Kendra Scott necklace and bracelet, and pearl clips. I truly felt like I had stepped out of an episode of Gossip Girl, and had saved the best look for last!


For me, this challenge was a good reminder that dressing up makes you feel your absolute best, and you don't need an occasion to do so! It's important to dress for you and to just wear what makes you happy, whether that means wearing a ball gown or just a pair of sweats. As Coco Chanel says, "every day is a fashion show and the world is your runway!"


XOXO,

Kristin


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