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I Let My Guy Best Friend Dress Me For A Week

If I had to call my style anything, I’d call it bohemian-grunge. I love anything Free People, and I’ll probably end up pairing it with Docs. The combo of ethereal and 90s aesthetics call out to me and are, I believe, a perfectly good way to create an outfit. Though I’ve never had anyone complain to me that my sense of style was off (on the contrary, I usually even get some compliments here and there). However, I have had people get confused by the fact that I’m pretty much a walking, talking fashion contradiction: one day I’ll pull the cutest outfit out of my closet and the next I’m wearing sweatpants and my brother’s old T-shirt.

Here I am with Oliver! This outfit is definitely representative of my usual style.

Obviously, I need some help when it comes to maintaining and further cultivating my fashion sense, which is why I recruited one of the more stylish people that I know to pick out a school week’s worth of outfits for me from my closet. Oliver is a theatre studies major, a junior, my best friend, and he’s also a fantastic dresser. His wardrobe of skinny jeans, striped sweaters, patterned button downs and messenger bags is truly envious. However, although Oliver works in the costume department I had doubts going into this experiment as to whether or not he would succeed in picking out clothes for someone of the opposite sex. Especially for one whose personal style is much different than his own, and particularly for someone that he knows so well (probably too well).

Oliver:”I would describe Olivia’s style as 70s inspired, she’s very free-spirit-esque. But she’s classy too. I agreed to do this experiment because Olivia’s my best friend, and I felt like this was a fun way to invade her personal space… I don’t know why she’s letting me do this, because I’m definitely going to make her wear the weirder stuff in her closet, but hey, she asked!”

DAY 1:

Dress (Marshalls, Brand: Soprano), Cardigan (Old Navy), Shoes (Clarks), Necklace (The Peace & Justice Center in Burlington, VT)

Day 1 consisted of a little black dress, a brown cardigan, black tights, brown leather booties and an orange beaded necklace. I was supremely impressed with this outfit, which was both very cute and very flattering. However, it is definitely far fancier than I usually dress for class, especially on a Monday. The necklace is one that I never wear, and honestly I can’t remember why as it really brought the whole outfit together and added a nice pop of color. All in all, I loved this outfit and I think that it really started the week off well.

DAY 2:

Sweater (J. Crew), Pants (Lane Bryant), Shoes (Lands’ End), Beanie (Faces in Northampton, MA) 

As Oliver was looking through my closet he kept talking about my “peasantry clothes” as he called them (a.k.a. anything bohemian looking or covered in patterns). He shied away from these items, preferring to dress me in a style that was more preppy than I was used to: hence my Day 2 outfit: a wool sweater with suede elbow patches, olive green pants, a burnt orange beanie and suede desert boots. Overall, I liked this outfit. I probably would never have put it together. If I had, I would have switched out the shoes for combat boots to add a little bit of edge, but It was definitely more casual, which I appreciated. Oliver said that he “kept forgetting I was a girl” and was basically dressing me like himself, which was admittedly weird, but also explained why my outfits had been so preppy up to this point.

DAY 3:

Dress (ASOS), Bracelets (Alex & Ani), Boots (Doc Martens) 

Ugh. Day 3 was absolutely freezing. Storrs winter is in full swing and I was dreading wearing anything other than leggings layered under sweatpants, which I knew was definitely not in the outfit plan. Today called for a black dress with ¾ sleeves and a patterned overlay, black tights, my floral Doc Martens and a few gold bracelets. I was excited about the cuteness factor of this outfit. However, after about five minutes outside I realized why this dress had been in the back of my closet for months: it’s very, very short. I spent most of my day pulling the dress down while simultaneously freezing to death in tights. However, I did get some compliments on both the dress and my boots (which are amazing), so I suppose that it wasn’t a total loss.

DAY 4:

Jacket (Patagonia), Jeans (Lane Bryant) 

Today’s outfit was extremely casual: jeans, a T-shirt and my fleece jacket. I personally didn’t mind this outfit, as it included my absolute favorite pair of jeans. However, Oliver wasn’t a fan of the jeans, especially after I told him that I got them on sale for five dollars (a personal point of pride) to which he responded, “Yeah, I can tell.” He paired the jeans with what he likes to call my “Scooby-Doo Jacket” due to its light brown color and blue accents. I liked this look, as it was both comfortable and reasonably cute. Oliver however, had other opinions which he clearly stated by saying, “This jacket makes Olivia look like Scooby-Doo, so I chose this it solely for embarrassment purposes… and comfort.” Thanks friend.

DAY 5:

Sweater (Clark University Thrift Store),  Jeggings (Forever 21 +), Boots (Doc Martens) 

Today’s outfit was surprisingly adorable and one of my favorites. It seemed very simple at first, dark wash jeggings, a grey sweater that I hadn’t worn in a while, and my floral Doc Martens. I had forgotten that this sweater has colorful flecks sewn throughout it giving it a really interesting quality. Additionally, the whole outfit was warm and comfortable, two major pluses in my book. Overall, I loved it because it was definitely an outfit that I would have chosen for myself; simple and stylish.


My favorite outfit was 100% Day 1, as it was both very stylish and comfortable and was reminiscent of my personal style. It also allowed me to try something a little different. It was hard to choose a least favorite look, but I’d have to say that it was probably Day 2. The sweater and olive pants combo was just a bit boring in my opinion.

Overall, I think that Oliver did a pretty great job picking out outfits for me and he really surpassed my expectations. Though sometimes he got frustrated during the process, frequently shouting things like, “God, I need a drink!” or complaining that so many of my clothes looked like something Diane Keaton would wear (she’s amazing, so I take that as a compliment), he did a great job and proved that the people you love really do know you best. Thanks Oliver!


Olivia is a Journalism and English double major who spends entirely too much time watching Netflix and is not even sorry about it. She loves to sing, write feminist musings, hang out with her pets and fantasize about a world in which everything tastes like Nutella. In another life she is best friends with Veronica Mars and married to Logan Echolls (and they're both totally cool with it). 
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