I Did A 30 Day Style Challenge, Here's How It Went
And the outfit I absolutely hated the moment I put it on.
I recently finished a 30-day style challenge over on my Instagram. Style challenges aren’t new, this is not some grand idea I had by any means. I remember obsessing over Kendi Everyday’s 30 pieces in 30 days challenges she’d do in the early days of blogging. I ate that shit up back in 2011. Anyone else remember her doing that? And while I didn’t stick to 30 pieces, the plan was to challenge myself to create 30 outfits in 30 days.
As someone who works from home and may wear loungewear for a few days in a row, this felt like it would be a big challenge for me. And I was excited about it. With winter behind us, and spring officially starting, now was the perfect time to play dress up with my clothes. Figure out what I am loving in my closet, styling new pieces and fine-tuning my personal style.
I knew I couldn’t guarantee there won’t be a day here and there where the outfit would be straight-up loungewear. And I think that may be just fine! From the get-go I was also already thinking I may need to be on a day or two delay so this isn’t a stressful experience, but a fun one. I even toyed with the idea of batching just a couple of outfits for those days I simply do not get dressed. But my goal was to keep that at a minimum and still wear the outfit I created on the day I woul dget dressed.
The point of this little challenge was to fine-tune my closet and help me find my style. As well as helping me to get over the learning curve of creating quick Reels on the fly. And I’m excited that I gave this a try! Here is how it went…
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I Did A 30 Day Style Challenge, Here's How It Went
Week One →
Thoughts On The Challenge So Far
My first week I realized quickly that yeah, I don’t think I’m getting dressed every day. So this isn’t going to be 100% authentic. And I was fine with that. I don’t think any influencer out there is honestly doing a real 30 for 30 challenge. And if they are, good for them! I think if I worked in a traditional office, that would’ve been easier. But because I work from home and there are days that I just do not get dressed. I often find myself in my workout clothes until 3, then shower and why bother putting an outfit on at that point?
By day five, I was done talking through my outfits. They are harder to edit and, honestly, don’t usually perform as well on Instagram. Creating video, editing it and uploading it to 3 platforms (YouTube, IG and TikTok), is time consuming. So reducing the talking was a need. And yes, I totally fell off the YouTube wagon, oh well.
This week felt like the start of any project. Excited and eager. I really tried to wear things I hadn’t reached for in a while.
The Looks
A lot of the first week’s looks were worn during colder days. So lots of trench coats and jackets. I did have one nice dinner out where I got more dressed up. I love the Sezane top I wore for that dinner. I also finally wore my new Freja New York bag out in the wild. My one and only complaint about the bag, and it’s MY fault, the shoulder drop is not long enough to wear on my shoulder. It’s definitely a handheld-only kind of bag. I love the East-West shape, though, so now I am hoping to find another option that can be comfortably worn on my shoulder.
Week Two →
Thoughts On The Challenge So Far
Week one flew by and I was finally in a bit of a groove once week two started. I also decided to bank an outfit this week (the skirt and jacket set). I knew that there would be a day that I just wouldn’t get good light in the apartment, or that I just wouldn’t want to get dressed. After chatting with a few friends who have done these challenges before, I realized that absolutely no one is doing these in real time. They are 100% banking content. And I think that is the way you should do it if you want to stay organized and not feel stressed about it. Because at the end of the day, this is supposed to be fun!
The Looks
These were some of my favorite looks. Both new outfits, like the leopard track pants that I shot the day before I wore them out IRL. And also a favorite outfit combo, my wide leg cuffed jeans with a trench. And another repeat outfit, denim on denim. This is one of my go-to outfits.
One of these outfits, the skirt and jacket set, was a look I banked to have on hand. I had just gotten the set and I adored it. I thought that pairing it with loafers and socks was a great way to show you all how to wear pieces for spring when it’s still early in the season. Adding earth tone pieces, socks and loafers is a good way to transition those more springy pieces. I have yet to wear this outfit IRL but plan to wear some variation of it soon because the weather has been so cold.
This was also a week I decided to share a true lounge outfit. I came home from the gym and showered and knew I’d spend the day at my desk in sweats. This Gap set is a true look I’d wear at home. I also played with my first pair of barrel leg pants (a quick favorite)!
Week Three →
Thoughts On The Challenge So Far
I was so glad I headed to Atlanta this week because the weather in NYC was TRAGIC. So very cold. We had one nicer day before I headed South (the brown skirt and tee) which felt like a dream. But since this was a spring challenge, I was getting a little annoyed that the weather was not cooperating with how I wanted to get dressed.
Being in the warmer temps in Atlanta made me instantly excited about spring clothes. I also felt like this was when I got really fast at editing and had a true routine down. The corner of my Atlanta condo where I shot also made me realize how pathetic my bedroom videos were of me getting dressed in NYC. I need to figure out a new backdrop in NYC as soon as possible. That was top of my to-do list when I headed back.
The Looks
I loved some of these looks so very much. The brown skirt, a favorite. The leopard shorts, will be on repeat all spring and summer. And the track pants and soft pull on pants are quickly becoming comfy favorites in my closet. These looks, I think, encompass how I want my spring vibe to feel. Comfy!
Week Four →
Thoughts On The Challenge So Far
This week had me feeling like I was almost sad to see this challenge come to a close. I am starting to brainstorm what I’ll do next, or if I’ll just start sharing my outfits every day more often now that it’s become second nature almost. There’s something fun about it being an actual challenge with a countdown, though, don’t you think?
The Looks
These outfits are a mix of NYC and Atlanta, and it’s chaotic. It was FREEZING in NYC and look 1 was worn with a wool coat. Criminal. Look 2 is going to be a favorite easy outfit but was a banked look in hopes I’d have a warmer day to wear it to a coffee shop to get some work done.
This week, I wore an outfit I HATED. Look 3, the faux leather blazer and straight leg jeans with Mary Janes. I have never felt so OFF in an outfit. Which is so interesting since all of the pieces are favorites in my closet. But together, not so much. I felt super business casual. Someone even messaged me to say “when I saw this outfit, I instantly thought I’d wear it to work”…exactly, it’s for the office! I’m glad I inspired someone, but I couldn’t rip this outfit off my body fast enough.
It really had me thinking about how I put outfits together. It was just a lot of business casual pieces in one look. And even though I thought the leather blazer would add the edge I felt the Mary Janes needed, it wasn’t enough. A true reminder to make sure you are balancing your outfits with your more than one style “words” to create balance and interest.
Final Thoughts On The Challenge
This challenge was designed to do just that, though. To play dress up, to fine tune my style and rediscover pieces in my spring wardrobe. You hear me say it a lot that you have to play dress up in your closet. Personal style is almost like a muscle. You have to practice and work at it.
Plus, sometimes you do have to have bad outfits you don’t feel good in, and that’s okay. It’s a reminder to to then better formulate outfits the next day. I think if you, Indigoer reading this, are wanting to try something like this, you can! Start documenting your outfits each day with a quick snap in the mirror and save them to a Notes folder or album on your phone so you can reference favorites and tweak from there.
This challenge also helped to remind me of my style words. What are style words? This is something that
dubbed, and it’s having 3 words that you use to craft your outfits. Everybody has their own 3 style words. I’m still figuring mine out, but I’ve mostly narrowed them down to the following.Effortless/Casual - I like pieces to be simple and streamlined that gives off an effortless feel. It’s unfussy and feels easy.
We all know I like a casual look. I lean towards sneakers, tees, comfortable jeans and so on. And I also love a slightly undone look. I think this also plays into me always having my hair wavy and not done perfectly.
Tailored/Structured - This one I am still debating, but I am someone who does love things to be tailored and not sloppy. I like a good structured blazer or jacket. And if I’m wearing something that’s super casual, I like to add more tailoring or structure over top to balance it.
Edgy/70s - I do like a touch of edge in an outfit. Whether it’s in an interesting and edgy shoe, or a graphic tee. And I love the 70s look but only like to have a smidge of it. Usually in a silhouette of denim or earthy tones.
I’m still fine-tuning this. But I think when I look back at all of these outfits from 30 days it gives me a good idea to figure out what those words are. Which makes it easier to get dressed. When you start to put an outfit together, you want to add in something from EACH category. It creates that balance and also interest to your outfit that makes it your personal style. We don’t want an entire 70s outfit or it’ll almost feel like a costume. And if everything in my outfit is tailored and structured, it might feel too stiff for my personal style. But mixing these pieces together with other items in my 3 words, can help to balance out an outfit and make it feel more like ME.
Will you be trying your own style challenge? I hope you followed along with me on Instagram. It was really fun. You can browse all of them on my Instagram here.
So inspiring!! Need to do one of these as a creativity challenge for myself 😂
Maybe 30 days (or whatever number) of styling jeans different ways?! I think most of us love and wear them often but get stuck in styling them the same way!