My Roommate Dressed Me for a Week and Here's What Happened

Last week, I had my roommate Abby pick out my clothes for seven days. She's Floridian, so her style is super beachy and comfy - which totally reflected in the way she dressed me for a week. Usually, I just ask her if my outfits are okay, or if I should wear one accessory over the other. She gives me pretty good advice, and everything she tells me to do with my outfits always is the right thing to do. I trust this girl with my life, and she made some really good decisions on my outfits for the week. 

Let me preface this by saying I am a control freak when it comes to my wardrobe. I pick out my clothes every night before the next day, and sometimes I even pick them a week in advance. I feel very strongly that clothes reflect who you are and that making good impressions is the most important thing for you to do. I also have a TON of clothes. I'm not even joking when I say I have more clothes in our room than we have anything else in our room. I have enough clothes to never repeat outfit combinations if I don't want to. 

All of the clothes featured in this article are things I own that Abby picked out and put together. The only guidance I gave her was what I was doing for that day, what the weather was going to be like and where to find my clothes/accessories.

I challenged myself and relinquished control of my wardrobe for a week, and was very pleasantly surprised.



Photo taken by Josh Heskel.

Day 1 was such a LOOK! I was obsessed from the beginning. Today, I had my psych class, an ASB meeting and an entire essay to write by midnight. For the first day, Abby picked out my fave pair of boyfriend jeans (a pair of $5 slim cut men's jeans from Gap I distressed myself, DIY inspo courtesy of my favorite boho blog), a tank by Blu Pepper that I purchased at my favorite upscale consignment shop (shouts to Sophie, Rhi, Christina and Becky), my fun flavored Keds (that I bought online on sale), my white canvas bucket hat from Gap, my slouchy beige sweater also from Gap and a little necklace with dried flowers in it.

This outfit felt so laid back and cool, so basically the complete opposite of me. I was really excited when she put this outfit together because I bought this tank top over the summer - I thought it was really cute but I hadn't worn it yet. Some weird part of me is scared to wear tank tops in the middle of fall (even if it gets warm), and it didn't stay as warm for as long this year in Boston. During this time of year, I typically shift my attention from my summery to my wintery wardrobe. Once fall hits, I need yarn to be touching my body at all times. This sweater definitely spoke to that side of me that constantly needs a "weather security blanket" (pun intended).

I GOT SO MANY COMPLIMENTS ON MY BUCKET HAT! My inner frat boy was screaming all day. I was so glad she picked a hat because *full disclosure* I was going on day 3 without a shower. Plus, every time I looked down at my shoes, I got hungry, but also happy. I was instructed to do minimal makeup with a nude lip, so I beefed up my eyebrows (which I also got complimented on by my friend Adam, and it basically made my day) and mixed two matte lipsticks by Maybelline, topped with a million coats of mascara.

Overall, I felt GOOD AS H*CK. Great day.



Photo taken by Abby Freeman.

Day 2 was deemed "gold accent day." Today I had my COM class, a CSC PR meeting, a HerCampus Editors meeting and I saw Sia in concert (!!!! I'm still yelling). Abby picked out my gold-studded mint tee from Forever 21 (I literally have had this since freshman year of high school), white paper bag shorts from the Sears Kardashian Kollection (also from ages ago), and my gold Steve Madden sandals (high-key they're my summer staple, low-key I'm too nervous to wear them in the city). She completed the look with my gold Alex and Ani Bracelets, gold octagon earrings from Madewell and a braided, gold ring I had made for me at the beach (appropriate af because both my ring and my roommate are from Florida). 

I'm going to be honest, I was cold. Like, really cold. And I feel so bad saying that because I know Abby is reading this, but I felt so cute. In her defense, the night before our weather app said it was going to be 79 degrees and sunny, but it was not. I loved the idea of the outfit and how it looked, but I felt so weird walking down Comm Ave in a pastel tee and white shorts while everyone else was bundled up and wearing all black. Part of that is my bad because I care too much about what people think, but I owned it the best I could before the evening.

I did gold eyeshadow that day (courtesy of Loreal Infallible) and a ton of highlighter because, why not. For Sia that night I kept the entire outfit, except I swapped my pastel tee for a black sweater. I kept the gold accents, but took my makeup look from day to evening by adding a plum shade from Colourpop. People on social media were OBSESSED with this look, and so was I. But I was left asking myself and also everyone on the Internet, "What's so great about a black sweater and white shorts?"

The world may never know.



Photo taken by Abby Freeman.

Day 3 made me feel so freakin cute. I felt the vintage-y 50s pedal-pushers-and-Keds vibes all day. Today was a rather chill day - class, homework, study session debate (DON'T GET ME STARTED). My tee is from American Eagle (go feminism!), the capris are from Gap, sneakers are white leather Keds (perfect for easy cleaning!), my sunglasses are from Garage (but are from ages ago) and my mom bought me my choker from a cute little store in Richmond, VA.

Today I felt super cute, but also super relaxed. AE's jegging tees are so soft, and the pants were so chill. I haven't donned a headband since I got all my hair lopped off, but I was totally digging the look. It was great, once again, because I was on hair day two, so I didn't have to worry about how greasy my hair was.

Abby took pictures of me doing my makeup for her photo project, so I did a little bit extra. I did sparkly eyelids and a navy liner, with mascara and a Too Faced Melted Metals liquid lipstick my mom got me for my birthday. Overall, I was really happy this day. It was a beautiful autumn day, and I felt really cute. 



Photo taken by Becky Hawryluk.

Day 4 I felt badass as h*ck! Abby thought she was making me too beachy for Boston, which is not true, but I wasn't dressing myself. She wanted to pick something a little bit more edgy because that's how I've been dressing lately. Thursday I had class, and my mom was arriving for Family and Friends weekend so I would get to see her fabulous self and go out to lunch. My shirt is Halogen from Chic Envy; my jeans, jacket and boots are from Gap and my choker is from Walmart (yes, that Walmart!). 

I felt super comfortable in this look the entire day. I felt this was the edgy version of me and I totally dug it. I felt really cool and powerful while carrying my friend's air mattress down Comm Ave for my mom to sleep on. I love the collection of earth tones Abby picked out - she even picked out my denim that has brown undertones. I was really impressed. 

Overall, it was a really great day. I listened to an empowering podcast and looked like I was going to drop kick the patriarchy (which I did). 



Photo taken by Becky Hawryluk.

Day 5 was a TRIP. I had class and a crazy test, a visit to Sephora opening in Fenway, and I was seeing my friends in The Addams Family that night. Abby wanted to stay in the cooler cold weather color scheme with grays and blues. My button down is Garnet Hill from Chic Envy, my tank top is from American Eagle, my jeans are from Gap Factory and my Chelsea rain boots are from Target. My necklaces are both from Forever 21.

Rain was in the forecast for today, but little did we know we were in for a torrential downpour. It was raining so much that we took off our shoes, closed our umbrellas and traipsed home with reckless abandon. Needless to say, we were soaking wet and ready for a hot chocolate. We had an amazing time, and that's why we forgot to take a picture of just me. So, here's this one. You can use it for blackmail purposes.




Photo taken by Becky Hawryluk.

Day 6 was the beginning of the best weekend of my life. I was celebrating my upcoming birthday by having brunch with my BFF, exploring South Boston, making a regular trip to Gap in Copley Square (my place of work, come visit!), and going to my friend's comedy show. Here, I am squinting in front of the Boston Public Library wearing a tee from JCrew Factory, a scarf from Marshalls, jacket and jeans from Gap and boots from Target. 

My girl today MIXED PATTERNS. I was so impressed. Like, I was floored. She originally had me wearing my taller patterned rain boots, but it wasn't supposed to rain that much so she let me wear my short black ones. I was also super nervous about wearing a scarf. That sounds bizarre, but I brought scarves to school thinking I would never wear them because lately I've just not been impressed by them. However, Abby totally proved me wrong and picked this adorable scarf to complete the outfit and give it some color on a chilly fall day.

I kept my makeup pretty natural again, except I added a pinker lip with my Lancome Juicy Shaker (in Piece of Cake) I bought at the Sephora grand opening. I love the color because it's like a more vibrant version of my own lip color. 



Photo taken by Becky Hawryluk.

Day 7, the final day of Abby picking out my outfits, was admittedly a very sad and very happy one. I was sad that it was my last day not having to worry about what I was wearing, but it ended up being one of the best days of my life. I went to Primark with my mom and had a pre-birthday dinner and TWO ice creams with Abby and a couple of my friends. My last outfit made me almost as excited as I was about the first one did. I felt so artsy and so cute. Abby picked out my Eileen Fisher waffle sweater from Chic Envy, a bralette from Aerie (not pictured), girlfriend jeans from Gap, white Keds and a huge scarf from Forever21. I also wore blue stud earrings and a ring. 

Once again, Abby had me wear a scarf that I was sort of iffy about at the beginning, but was completely obsessed with as the day went on. I wore it a bunch of different ways - wrapped around my neck in the pic above, and also wrapped around my arms like a shawl in the pic below. I chose to wear this Hillary Radley coat I got at Goodwill with my mom, which is real wool and only $18. I put my hair in a topknot because Abby always loves when I do, and I used the new Urban Decay Naked Basics palette for my eyeshadow. I used the beige color "Nude" and the copper tone "Extra Bitter," which I think accurately describe who I am at all times. 



Final Thoughts

Abby singlehandedly restored my (and my mom's) faith in scarves. Honestly, this year I had given up on them, but now I'm going to give them a chance. Abby picked out things for me that I never would have thought of putting together, and she picked out things that I haven't worn in a while. She made me rethink the way I was picking out my outfits every day. I'm finding that since I watched her pick out my clothes, I'm going to make more unexpected and bold choices in my wardrobe. She awakened my inner Floridian.

This week was an incredibly challenging and freeing week for me. It was really hard for me to not be constantly in control of my appearance for a long period of time. Sometimes I had to convince myself not to freak out. It wasn't even because of the outfits themselves - I loved them. It was the idea of not being able to control one of the only things in my life that I have the ability to control. However, once I let myself not care and really trusted Abby, it didn't bother me as much.  If you have good base wardrobe, anyone can pick outfits for you. If all of your clothes make you feel good and exemplify who you are, there is almost no outfit that you won't like, or would look bad on you.

I am so, so happy that my roommate Abby picked out my clothes for a week. It allowed me to relax and focus on self-care for a little bit longer throughout the day since I didn't have to worry about my clothes. She made me feel beautiful, and for that I am so grateful. I love her so much and I feel like this experience brought us closer together, and made me appreciate her sense of style even more than I already did.