If you follow me on Instagram or TikTok, then you’ll know that last week I let a random number generator choose my outfits. What does that mean, you may ask? Since I track all my clothes in a cost per wear spreadsheet, I decided to assign numbers to all my tops (sans sweaters—it was too hot last week) and all of my bottoms. I then spun an online “wheel” to choose a number for both the top and bottom to create the base outfit. Was the entire outfit randomly generated? No. But I decided I needed some leeway with layers, accessories, etc. in case the two pieces didn’t match at all. It turned out to be such a fun exercise in stretching my closet and looking at my clothes in a way I never have before.

Day One

Started off so strong with this outfit (full video here). Of course, it’s no surprise when one of the random pieces was one of my favorite pairs of jeans, which go with nearly everything. Even so, I tried to push myself and style the outfit differently than I normally would have. It took a couple of iterations, but I landed on wearing this striped hair scarf as a sort of tie/ascot underneath the collar, which I think turned out so stylish (and on trend!). The maroon velvet flats felt like they were out of my comfort zone at first until I realized they matched one of the stripes in the scarf perfectly. I can’t help myself. The only thing I would change in this outfit next time is that I wish I added a belt! I don’t love how the length of the top lands exactly where the jeans start, and without a belt it just looks to me like something is missing.

Gingham Top: Hand-me-down, last worn here | Jeans: Express, $15 ($0.26 per wear), last worn here | Flats: Sundance, $60 ($3.16 per wear), last worn here | Scarf: Hand-me-down | Purse: Kate Spade New York, $110 ($11.00 per wear), last worn here

Day Two

Day two was… less successful. In fact, it may have been my least favorite outfit of the week. You would think a white top and white pants would lead to infinite possibilities, but I actually felt really stuck with the monochromatic look. I knew I wanted to try to style this blue jacket with it (which I hadn’t worn yet—this year or ever), but I think that was my first mistake. I ended up adding a bunch of silver accessories and calling it a day until my boyfriend said I look like someone from a Eurovision music video (very futuristic, lots of metallics, etc.). To be fair, he didn’t mean it in a bad way and actually liked the outfit, but it ruined it for me.

I went back to the drawing board and ended up wasting a lot of time for what was ultimately a pretty boring outfit. Orange and blue is one of my favorite color combos (even if it is Bronco-y), and I loved the little pop of orange in my Ziggy Stardust earrings, which you can’t really see in this pic. But ultimately I did not feel confident in this outfit and would not wear it again.

White Blouse: Thrifted, $12 ($0.71 per wear), last worn here | Blue Jacket: Clara Sunwoo, gifted by brand, last worn here | White Jeans: JCPenney, $25 ($2.08 per wear), last worn here | Orange Flats: DSW, $13 ($0.62 per wear), last worn here

Day Three

At first I thought there was no way I could make this grey/blue “Love” graphic tee and yellow printed pants work together, but in the end I think it turned out to be a really stylish outfit! I felt very “cool girl” and was proud of myself for putting something together that I wasn’t embarrassed to be seen in. The top and pants did seem very pajama-like at first, but the black denim jacket added structure while tying in some of the colors of the pants. The real star of the look, though, is the mustard yellow earrings, which did wonders to pull the whole outfit together. I firmly believe this look would not be the same without the earrings.

Tee: Philly airport gift store, $25 ($3.13 per wear) | Black Denim Jacket: Topshop, $55 ($1.17 per wear), last worn here | Pants: Clara Sunwoo, gifted by brand, $135 ($27 per wear), last worn here | Sneakers: JustFab, $50 ($2.63 per wear) | Maroon Purse: Nordstrom Rack, $50 ($1.92 per wear), last worn here

Day Four

Day four’s outfit turned out to be cute, but not out of my comfort zone at all. This is very much an outfit I would have styled normally (not actually, because I wouldn’t have paired this black velvet top with my grey ripped jeans, but generally speaking it is very on par with my usual fall outfits). I wasn’t disappointed, though, because I hadn’t worn the belt, shoes, or purse yet this year, so it was a successful outfit in other ways. The only interesting thing about this look is the sparkly beaded purse, which you can’t see great in this pic. At first I thought it was too much for daytime, but then I thought, “When else am I going to wear a sparkly purse? I should just do it!” And I’m glad I did.

Black Velvet Top: JCPenney, $15 ($1.36 per wear), last worn here | Maroon Jacket: BB Dakota, $25 ($0.30 per wear), last worn here | Grey Jeans: Express, $24 ($0.92 per wear) | Boots: Portland Leather, $95 ($11.88 per wear), last worn here | Belt: Unknown, $50 ($1.61 per wear) | Purse: Francesca’s, $20 ($2.86 per wear), last worn here

Day Five

This is the first outfit that I did not wear. When I rolled for this one-shoulder green blouse and my navy polka dot shorts, I thought there was no possible way I could make them work together—the styles, the fabrics, etc. were just too different. I still finished styling the outfit just to see it through, and I decided on a denim jacket (to cover the blouse) and big silver earrings, thinking they might distract from the rest of the look. I added my unique face purse to say, “I’m funky and I wear funky outfits!”

A handful of people commented on this outfit and said they think it’s actually pretty cute—or at the very least, not so bad that I shouldn’t have not worn it. I’ve given this look a lot of thought since. I still stand by that I don’t think it’s good. However, I will admit that it’s not as bad as I originally thought. I kind of wish I had worn it anyway just to see the series through.

Green Top: Local boutique, $20 ($20 per wear), last worn here | Jean Jacket: JCPenney, $19 ($0.08 per wear), last worn here | Polka Dot Shorts: Kohl’s, $36 ($2.12 per wear), last worn here | Silver Sneakers: JustFab, $50 ($4.17 per wear), last worn here | Face Purse: Boutique, gift, last worn here

Lessons Learned

Overall, I had so much fun putting together this series and dressing completely out of my comfort zone. My first big takeaway is that I love to be matchy-matchy in my outfits. There’s nothing wrong with that, but it can be kind of boring sometimes (and some might argue “out of style” at the moment). I’ve been following some new people on TikTok lately that wear really fun, funky, colorful outfits that have been inspiring me to get more out of my comfort zone. And I think the key to doing that is accepting accessories and pieces that don’t match perfectly but just “go” (as Stacy and Clinton would always say).

My second big takeaway is that my accessories are seriously lacking in color and variety. There were so many times during this experiment that I found myself thinking, “If I only had earrings that were this color,” or, “If only I had a purse in this color.” Accessories can do SO much to tie an outfit together. I tend to lean towards neutral accessories that go with everything, but this was a really good reminder that I should look for more unique statement pieces that really make an outfit.

In case you missed the series on social media, here are all the full videos and thought processes behind each outfit:

Randomly Generated Outfits: Day One

Randomly Generated Outfits: Day Two

Randomly Generated Outfits: Day Three

Randomly Generated Outfits: Day Four

Randomly Generated Outfits: Day Five

Randomly Generated Outfits: Reflections

I want to do another randomly generated outfits week soon, probably in the winter so I can work in all my sweaters! It was such a good way to look at my clothes differently and feel excited by what’s already in my closet.

 

Miles of smiles,
Grace