I Let A Website Dress Me And This Is What Happened

Remember that scene at the beginning of the classic 90's chick-flick "Clueless" where Cher uses her now archaic desktop computer to plan her outfit for the day? Remember how desperately you wanted your own little machine to match your plaid skirt with your plaid blazer? Well now it (sort of) exists! Enter Daily Dress Me, a site created by California-based Nina Vir when she was in high school, that helps you choose your outfit for the day based on the weather.

I had a few reasons for wanting to test out Daily Dress Me. First, living in Boston means you can sunbathe in the Commons on a 70 degree day and then cozy up for snow the next (this actually happened a couple of weeks ago). Having a website tell me how the weather will change over the day and what outfit won’t leave me freezing or sweaty seemed like a pretty neat idea. Second, as a college student trying to balance homework, extracurriculars, and "Portlandia" binging, I was eager to see if I could shave some time off my morning routine and make life just a little easier. And finally, I’m in a total style slump. I high-key hate most items I own but have no idea what kind of clothes I actually want to wear. I thought testing out this site would be a good way to experiment with different styles and find a new one for me before committing to an expensive wardrobe overhaul.

Here’s how my experiment went!

Day One: Thursday, 22 February

Forecast: Snow. Mostly cloudy. Low 37°F. Winds NNW at 10 to 20 mph.

Daily Dress Me outfit: Bloomingdales grey ruffle neck sweater, grey coat, black skinny jeans, and black heeled boots


                                                                                                             Courtesy of Daily Dress Me

What I wore: Grey Northeastern t-shirt, grey blazer, black flare jeans, and black boots with gold embroidery

                                                                                                                Courtesy of Yazmine Lomax

Effects on morning routine: I struggled a little to match this outfit as I don’t own a long coat. Actually, that’s a lie – I own a killer burgundy number that I stupidly left at my parents’ house in Australia. I decided to match the Daily Dress Me based on style rather than utility so I threw on my grey blazer and packed a warmer coat to wear out and about. I realize this probably defeats the core purpose of the site a little but I’ll take it as a lesson learned for tomorrow. Underneath my flimsy outer layer, I was torn between a black sweater or a grey t-shirt, and again chose aesthetic over practicality. However, I really liked the grey-on-grey look which I haven’t tried before. Since I was more about matching the look rather than the utility of the Daily Dress Me outfit, I struggled a little bit with holding my coat while getting out of my apartment which made my morning routine a tad more complicated than usual.

Who I felt like: This look had the sleek sophistication of an Olivia Palermo outfit though she pulls this style off a lot better than a scruffy, sleep-deprived college student like me!

Nina’s Thoughts: “During the wintertime, it’s really easy to fall into a routine of black on black on black, so I love a grey coat to lighten things up!”

                                                                                                                Courtesy of Pretty Designs

Feedback: A little girl on the T told me she liked my gold-embroidered boots – I wear them rarely, but since I don’t own any plain black ones like in the Daily Dress Me outfit (shocker, I know), I was glad of a chance to wear them and bask in the compliments. Plus, a friend with killer style in my literature class told me she thought I looked "really nice today." It seems like sophistication with a twist is working for me.

Day Two: Friday 23 February

Forecast: Rain. Partly cloudy skies this morning will give way to cloudy skies and rain during the afternoon. High 41°F. Winds SE at 10 to 15 mph. Chance of rain 70%.

Daily Dress Me outfit: Bloomingdales grey collared shirt, black coat with fur lining, black leggings, and black heeled boots.

                                                                                                             Courtesy of Daily Dress Me

What I wore: Black leggings, chambray collared shirt, leopard coat, and black Converse

                                                                                                                Courtesy of Yazmine Lomax

Effects on morning routine: This outfit took a bit of time to put together in the morning because it didn’t really work for my schedule for the day. I had a friend visiting from out of town so planned to walk the Freedom Trail with her and heels would not be suitable. Plus, I again don’t own the recommended outer layer so compromised by choosing a faux fur coat to draw on the fur lining in the Daily Dress Me outfit. Neither the Daily Dress Me coat nor the one I owned had a hood for the forecasted rain, so I accessorized with my Patriots hat, which actually looked pretty cool with this look. I loved getting the opportunity to wear my collared shirt, which has been neglected at the back of my wardrobe for a few months now, but it required some last minute ironing. I usually just slip on a t-shirt which is definitely easier in my morning routine but not as stylish.

Who I felt like: Although pretty far from the coat recommended in the outfit, the leopard coat reminded me of Alexa Chung who originally inspired me to buy this bad boy a few years ago. I was reminded how much I love her style and it’s evolution – perhaps someone I can look to for pointers in the future?

Nina’s Thoughts: “Fur coats make you look put together instantly plus they keep you super warm. Win-win.”

                                                                                                                Courtesy of Daily Mail

Feedback: I didn’t get any comments today, but I did get a few funny looks from passersby when I was taking this picture on Beacon Hill. Note to self: America is not yet ready for an outrageous leopard coat outfit.

Day Three: Saturday 24 February

Forecast: Mostly cloudy. A mix of clouds and sun during the morning will give way to cloudy skies this afternoon. High 54°F. Winds NW at 10 to 15 mph.

Daily Dress Me outfit: Bloomingdales navy sweater, black coat, light denim skinny jeans, and black studded flats

                                                                                                             Courtesy of Daily Dress Me

What I wore: Blue t-shirt, black puffer jacket, denim skinny jeans, and Converse

                                                                                                                Courtesy of Yazmine Lomax

Effect on morning routine: This outfit was quite plain so I had to spend some time in the morning finding ways to accessorize it. I ended up choosing a pair of gold and black earrings, and bought a pair of yellow sunglasses in Cambridge later in the day that added to the look nicely.

Who I felt like: This outfit didn’t give me a lot of feelings!

Feedback: My friend agreed the outfit didn’t really evoke a lot but was a good base for accessories. It works as an easy go-to outfit that I’d probably wear when I’m studying at the café across the street or nipping to college.

Nina’s Thoughts: “This is a fool-proof outfit formula: your favorite denim, your go-to winter coat, and your everyday sneakers or flats.”

There ya go! In a little experiment that could be a plot line on the next season of "Black Mirror," I let a website dictate a large portion of my life for a few days. While I had to spend some time coming up with substitutes for pieces I didn’t own, it did prompt me to try outfits I hadn’t considered before and taught me that my style is a little quirky. Plus, the layers in the outfits meant I was always dressed appropriately for Boston weather's mood swings!