I Put My Confidence To The Test And Tried Overdressing For A Week — Here's What I Learned

Grocery store shopping, but make it fashion.

When it comes to putting an outfit together, my main priority is always comfort. And while I hope my ensemble is aesthetically pleasing, I'm sure we've all heard the saying about how we need to feel comfortable in our clothes in order to be more confident. Which is why I thought I'd put said confidence to the test and try overdressing for a week. For the experiment, I spent time in low-key informal environments (think: bookshops and grocery stores) while dressed in outfits that were far from casual. 

This was the approach I was going for: 

I Tried Overdressing For A Week

OK, I wasn't going to be that over-the-top, but you get the idea. However, I noticed one thing when I looked through my closet: I don't actually own a lot of decadent, flashy pieces. And fashion, of course, is subjective, so while some looks may seem extravagant to one person, another might not share the same perspective. With this in mind, I set three rules for myself each time I stepped out in my "overdressed" outfit: I must stay in the location for at least 30 minutes; I must wear at least three pieces of clothing (including shoes); and I must incorporate one "standout" item in the look. It should also be noted I live in Los Angeles — and I've seen everything from people dressed in sweats to women who looked like they just came from a photoshoot out in public on the same day, so I really didn't know if I was going to stand out or not. Ahead, I documented each look along with the pros and cons of the experience. 

Look 1: 

Location: Huntington Gardens & Museum 

Outfit: White Long-Sleeve Top, Gold Lamé Skirt, Black Slide Loafers 

Standout Item: Gold Lamé Skirt

This Is What I Learned From Overdressing For A Week

This was my first time visiting Huntington Gardens, so I had no idea what to expect. For the occasion, I chose to pair a simple white top to balance out the metallic gold midi skirt and tied the look together with black slip-on loafers. I was pleasantly surprised I unknowingly coordinated with the gold drapes in the museum, and posing on the grand staircase made me feel less out of place. But, let me say, backless loafers are not the best type of shoes to wear when you're walking around gardens for an hour and are trying to make as little noise as possible in a library. Also, it was particularly freezing that afternoon, and while all the other visitors were bundled up in padded jackets and jeans, I was the only person within a mile wearing a skirt. I didn't receive any uncomfortable stares, but I did find myself wishing I had more layers — and different shoes — on. Overall, I would wear this outfit again if the day was warmer and involved less walking. 

Look 2: 

Location: Whole Foods

Outfit: Silver Fringe Jacket, Black Turtleneck, Black, Skirt, Tights, Knee-High Boots, Red Purse

Standout Item: Silver Fringe Jacket 

This Is What I Learned From Overdressing For A Week

For a trip to my local Whole Foods, I donned a silver fringe jacket over an all-black ensemble and added a bright red purse for a pop of color. Unlike before at the museum, I felt extremely overdressed from the moment my friend I and stepped out of the car in the parking lot. It might not be visible in the photos, but the jacket was decked out in sequins, calling more attention to the statement item. Once we were in the store, it was clear I was the only one who wasn't dressed in a shirt-and-pants combo. After a few minutes of perusing the wine section, a man passed me and my friend in an aisle, and after evaluating our two (very) different outfits, gave me a wide-eyed confused expression. Eventually, I began to have fun strolling around in my boots and party-ready look. I wasn't bothered by the glances and just enjoyed myself. I would probably only wear this outfit again for a holiday party or dinner. Bonus Tip: Whole Foods is a prime location for colorful backdrops. 

Look 3:

Location: The Last Bookstore

Outfit: Plaid Blazer, Blue Overall Dress, Tights, White Ankle Boots 

Standout Item: White Ankle Boots 

This Is What I Learned From Overdressing For A Week

One of my favorite places in LA is The Last Bookstore, so I chose to test out a not-so-subtle outfit while I added a few more books to my collection. Win-win, right? I call this look: '60s British bookworm. First, I learned while the boots may be very sleek, they are not quiet. Walking up the staircase, I felt like the entire second floor was being notified more people were making their way upstairs. And, yes, they are very Austin Powers but the white hue and block heel helped to elevate the ensemble and give it a mod touch. It's not the most over-the-top outfit, and I didn't get any double-takes, but I still felt like the outfit was a bit much for a bookstore. I would most definitely wear it again if I were to visit the National Art Library in London. 

Look 4: 

Location: My Local Neighborhood 

Outfit: Blue Shaggy Jacket, Floral Dress, Tights, Knee-High Boots

Standout Item: Floral Dress

This Is What I Learned From Overdressing For A Week

This definitely isn't my go-to dog walking outfit. I wandered around my neighborhood with my friend's dog, Louie, in a shaggy blue jacket, colorful floral dress, and black tights. I topped off the look with matching knee-high boots that were actually comfortable given the amount of time spent outside. I definitely received a few glances, but to be honest, I think people were more interested in Louie than my outfit. A woman who was also walking her dog actually stopped me to ask where my coat was from (Zara) and complimented my look. I don't think I'll wear this ensemble again for a leisurely stroll, but it would definitely work for a more festive occasion. 

Look 5:

Location: Coffee Bean And Tea Leaf

Outfit: Blue Coat, Pink And White Striped Jumpsuit, Orange And Pink Flats 

Standout Item: Pink And White Striped Jumpsuit

This Is What I Learned From Overdressing For A Week

I stopped by Coffee Bean And Tea Leaf in my final look of the week: a baby blue coat, striped jumpsuit, and vibrant pointed flats. I don't usually wear so many eye-catching colors at once, so this outfit was definitely out of my comfort zone. I was self-conscious at first because everyone around me was dressed in neutral hues and outfits appropriate for a rainy day. However, after a couple blocks, I didn't feel like all eyes were on me and started to feel more comfortable. Once I was in the store, a few people stared but then quickly went back to what they were doing. I ended up really liking the combination of bright colors and would wear this look again — even to a coffee shop! 

Final Thoughts:

This experiment pushed me to rethink the way I put outfits together and really take a look at the items in my closet. It made me realize comfort is still the most important thing, despite how cute those backless loafers are. Overall, I enjoyed the idea of dressing up more for occasions that don't necessarily call for it because it gives you an excuse to wear things that might have been sitting in your closet for a while — and the worst that can happen is you receive a few lingering stares. I learned confidence is not only about comfort, but also how you carry yourself. So while I may have felt self-conscious on the inside, I didn't let it show, and I think people responded to the way I presented myself. I also noticed I'm seriously lacking in pieces worthy of the KiraKira Instagram effect — and I need to get on that ASAP.