I Let My Grandma Pick Out My Outfits For A Week

by Hayli Goode

It may be sound like risky business to some, but I was not worried at all about asking my grandma to dress me for an entire week. While I don't necessarily follow the "grandma style" (my mom may argue differently), my grandmother and I have always had similar taste in fashion. And men, actually. (Not mad about that either.) What was scary, however, was asking my grandma to FaceTime with me. I am admittedly not patient when explaining technology to anyone, and she's still learning how to use email with the iPad my parents gave her for Christmas last year.

My grandma is a master planner. She chooses her outfits every week by pairing pants and a shirt, then folding them up together in her drawer. Since I have visited her at work in the past, I figured that the ensembles she picked for me would mostly be made up of slacks and printed cardigans — aka her very adorable uniform. I was surprised, however, when I noticed that when picking out the outfits, she was considering my personality, what my schedule was for that day, and my own fashion tastes. Not only did she pick out outfits that I would actually wear, but my co-workers and friends even complimented my clothes.

My favorite part wasn't her picking out pieces that hadn't seen life outside my closet in a while, or complimenting my neutrals-only repertoire (take that, mother). When we were picking accessories, she hated that I didn't have enough earrings for her to choose from. "I need to get you more earrings, Hayli," she insisted by the end. Fine by me, Grandma. My other favorite part? We FaceTime once a week now. Here's how it all went down.


My grandma totally understood the need to start the week comfortably. She doesn't quite understand that my full-time job is at a fitness magazine, which means I wear sweats to work the majority of the week. But black jeggings paired with a sweatshirt disguised as a blouse is close enough for me! And while this wasn't the most "dressed up" outfit, she advised applying red lipstick, which instantly made it go from casual to wow! My co-workers gaped at me wearing lipstick, but said I should do it more often. And I may. Although I didn't run into anyone besides them, I felt confident, fierce, and therefore productive all day.


Before choosing this outfit, my grandma asked if I had any plans for the evening. Typically, the answer would consist of CrossFit before TV and popcorn, but on this particular Tuesday, my parents were coming into town to see Wicked. I needed to dress up a bit, but not go full ball gown. Because this skirt is my grandma's favorite (she tells me that every time I wear it), she thought it would be perfect for a play.

I would have gone a bit fancier, but I absolutely loved this outfit. And I would not have assembled it myself! Tying my shirt up at the front? Never would I have done that voluntarily. It looked a lot better than I imagined. The only part of this outfit I would have changed were the boots, but my co-workers and parents told me that they liked them with the skirt.


Of course my grandma found the one bright item I have in my closet: this red shirt. I suppose it was easy to spot amongst the blacks, browns, creams, and grays. She then matched it with these printed "MC Hammer pants," as she called them. While I wasn't mad at the outfit, it was louder than what I would have picked out. I totally felt like it was grandma-esque when she insisted I should bring a sweater to work.

Despite my reservations, my co-workers actually loved the look. They were so surprised to hear that I was still doing the experiment. One even stated that their grandma would never pick out anything with such excellent prints. Which just proves that I don't have a regular grandma — I have a cool grandma. They insisted we grab drinks after work, just because everyone *magically* dressed up at the office that day. When we left that night, I was so happy to have the sweater. This was definitely my favorite look of the entire week.


This dress was hiding in the back of my closet, and I forgot how I much I loved it. It's long enough for me to feel comfortable sitting down at work, and is acceptable for any setting, from work to happy hour to dates. Which is exactly why my grandma picked it for Thursday. She even insisted that I wear my spiky boots instead of my short heel-less black ones. And I can never find a reason to wear the long, formal diamond earrings she paired with this look. I wore them to my high school prom (reserve judgment — they're adorable and classic), being absolutely obsessed with them at the time.

When I first walked into the office, my boss Z-snapped me and told me I looked fierce and very professional. She was impressed with my look, and said I should wear it at our year-end meeting. I didn't have anything going on after work today besides a CrossFit class. Typically, I avoid wearing dresses for long lengths of time because I hate feelings my bare legs touch, but with the help of anti-chafing Spandex shorts, this dress made it through the workday comfortably.


Casual Fridays at business-casual offices typically mean this type of outfit. At my office, however, this was dressed up for casual Friday. Still, I thought my grandma's pick of TOMS boots, cuffed jeans, a loose sweater, and colorful scarf was absolutely adorable. I actually have put this outfit together with a different scarf. Her choice of hairstyle also brought my back to my junior high days.

While it pained me to watch my co-workers in sweatpants while I wore skinny jeans, overall I felt comfortable and, again, productive. After all, I was more dressed up than I would be on a typical Friday. And I was able to go right to dinner after work without changing!


Before choosing my outfit, my grandma asked what I typically did on Saturdays. I told her that, besides a short run, I preferred to not leave my apartment and Netflix queue during the day. Apparently, my grandma has got athleisure down. She dressed me in my new favorite running tights, my favorite I <3 NY shirt (which I proudly snagged for $3, because you're never not a tourist in the city), and no shoes. She specifically told me to put on socks but not shoes. Don't have to tell me twice, Grandma.


My grandma really wanted to wear a skirt to my sister's wedding in June 2014. A couple of weeks before the wedding, she "practiced" wearing a skirt to church. As she was sashaying down the sanctuary, however, she had a friend rush up behind her and, standing about two centimeters away from her, warn that her skirt was caught in her underwear. My grandma hadn't worn a skirt to church in over a year before that, and now vows to never wear a skirt again.

Because she can't, apparently I have to wear a skirt to church. She called this my "Grace Kelly" look because it was very minimal, with no jewelry and neutral makeup. I was also pleasantly surprised that she chose brown shoes to go with this instead of black boots, because it's exactly what I would have done.

Is Grandma My New Personal Stylist?

Yes. I am calling my grandma to dress me for the week every Sunday.

But, seriously, I was very surprised that I liked the majority of the outfits she picked out, save one or two small things that I would have changed. I knew that my grandma and I had pretty similar tastes, but I figured that the outfits she picked out would look much like her typical uniform of dress pants, a blouse, and a cardigan. It just goes to show that you don't necessarily lose your sense of style after you hit a certain age.

What I loved most about this experiment, though, was finding a new way to communicate with my grandma. I'm honored to be her first-ever video chat, and now I look forward to our weekly FaceTime dates (during which she tells me what to wear during the week, and I hear innovative new ways to clean my apartment and make delicious meals).