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My friends picked out my clothes for a week. Here's what I learned about style and self-confidence.

I thought I'd get some much-needed wardrobe inspiration, but in the end, I learned a lot more about myself.
Image: What to wear tonight?
Bored with your wardrobe? Don't shop — enlist some friends to style a few outfits for you. kupicoo / Getty Images

No matter how fabulous the clothes, we’ve all been there. We open our teeming closets, dressers and handy under-bed storage bins with a sigh and a frustrating thought: I have NOTHING to wear. If it happens to Carrie Bradshaw, it happens to the best of us, and this summer, I found myself stuck in this very style rut.

I’m not unhappy with my style or my clothes, but I cycle through the same six outfits over and over (which, for me, means navy, navy and more navy). I sometimes struggle with body image and a lack of confidence with new trends, and I’m sure I’m not alone in that. I wasn’t certain how to get out of the boring, neutral trenches. My problem definitely wasn’t a lack of clothing, but a lack of new ideas. I wanted to call in reinforcements for a fresh take — my friends.

Our friends are our kindest mirrors. They always see the things in us that we want to hide or don’t think we have the confidence to pull off. How often have we each been told by a friend we totally need to try on that cool new item, only to shrug them off and put it back on the hanger? I asked my two roommates, Jenny and Julie, to dress me for an entire week to see if I could get out of my fashion lows and maybe even boost my self-esteem.

Putting my wardrobe — and friends — to the test

We’ve been friends since college, and I’d trust either of them with my life. But I wasn’t sure how I’d feel once I’d trusted them with my wardrobe. We set a couple of ground rules before they set out to plan 10 outfits for me:

  • They could dress me in anything from our three closets.
  • They could dictate my hair, makeup and jewelry in addition to clothes and shoes.
  • I was not allowed to veto any looks, and would keep mum during the planning process. Even if I really hated something, I wouldn’t be allowed to say so.
  • I would document each look with a mirror selfie, keep a diary and note any reactions from others.

Never one for a mirror selfies (in part due to the confidence issue), I looked to the experts of Instagram for inspiration. I practiced a hybrid of the Eva Chen “baby giraffe pose” and Chelsea Fagan’s seemingly effortless “I just threw this together” smirk and started snapping away. I’d be pushing myself out of my comfort zone by documenting my day to day looks so closely both before and during the experiment.

Finally, I turned to my beloved “amateur” experts for the clothes themselves. Over the course of a few hours and a glass or two of wine, Jenny and Julie selected my outfits, both together and separately. Jenny, who sticks to clean lines and sophisticated neutrals with her own style, had me try on a lot of her clothes. She put me in things that were from my own closet, but styled in a different way. “This is stressful, but fun ... I want to dress you in all the things I could never wear but look great on you,” she said as she looked over my collection of pencil skirts.

Emily Pandise and her amateur stylists/roommates, Julie and Jenny
Emily Pandise and her amateur stylists/roommates, Julie and JennyEmily Pandise

Julie gravitates to a more colorful and feminine look, and loves a good pattern. She and I share clothes quite a bit, so this challenge, she says, put her on the spot a little: “There was a moment of next level of comfort zone for you — it’s not out of my comfort zone, because they’re my clothes...but what’s the look that’s slightly different than what I would have [usually] picked for you?”

The night before the experiment began, I had mixed emotions. Jenny and Julie had picked out a lot of things I loved — but also things I would never wear together, never wear at all or would definitely never wear with the intention of photographing myself for all the internet to see. I was nervous not so much for how I’d look; I knew my friends had done their job well. I was more anxious about how I’d feel. Clothing is such a personal expression, and I was scared that my clothes wouldn’t be reflective of me, or that I’d be self-conscious the entire week.

Look #1: A sweater tank and jeans from own closet and my roommate's earrings
Look #1: A sweater tank and jeans from own closet and my roommate's earringsEmily Pandise

My first look was for a Friday night out with a friend to see a play. Jenny picked this one — a sweater tank from my closet (my mom picked it out, I don’t like how it emphasizes my upper body so I never wear it), my jeans and sandals and Jenny’s earrings. I was pretty comfortable in this — basically all my own clothes, just not styled in a way I would usually wear them. Of course, my friend commented on liking the top as soon as she saw me. Jenny and my mom have this one right.

Look #2: A dress from Jenny, necklace and lip color from Julie and my own shoes.
Look #2: A dress from Jenny, necklace and lip color from Julie and my own shoes.Emily Pandise

Next up were my normal days at work. First, a dress from Jenny, necklace and lip color from Julie, and my own shoes. A few of my coworkers knew I would be doing this experiment at some point, but I hadn’t told them when. They both saw this outfit and figured out immediately what was going on. I liked this dress/necklace combo on the hanger, but it didn’t feel super “me,” especially with the bold lip. The dress is similar to what I’d usually wear, but a different cut. Overall, I’d try this necklace idea another time, but will save the high-maintenance lip color for special occasions (too much for a normal work day).

Look #3: My white blouse, a skirt from Julie and my sandals and earrings
Look #3: My white blouse, a skirt from Julie and my sandals and earringsEmily Pandise

Tuesday’s look was my white blouse (again, don’t wear it that often), a skirt from Julie, my sandals and earrings (which, granted, I went out and bought after seeing them on another friend). The pink lipstick is mine, but I’ve maybe worn it twice. My coworker, who didn’t know my roommate had picked it out, said she liked it but that it was more color than she usually sees me wear. This skirt isn’t something I’d ever really pick off the rack. I usually stick with simpler or more classic patterns (big fan of the tasteful leopard print), but I always love it on Julie. This felt more “me,” but not my usual comfort zone. If I borrow it again, I’d wear with a simpler black top instead. I like this so much I’ll be looking for more patterns like this to permanently add to my wardrobe.

Look #4: Julie's shirt, my navy work slacks, Julie’s green vest, a necklace I’ve had since college, and my favorite summer sandals
Look #4: Julie's shirt, my navy work slacks, Julie’s green vest, a necklace I’ve had since college, and my favorite summer sandalsEmily Pandise

For my third day at work, another Julie-styled outfit: a shirt that had originally been hers, but I’d grabbed from a giveaway pile, my navy work slacks, Julie’s green vest, a necklace I’ve had since college and my favorite summer sandals. My friend who was in on the gig said she liked it a lot — but could tell it totally wasn’t my usual style, and I agreed with her. I loved this look in theory — the brown lip, the vest, the glasses — but I would have never had the guts to put it all together. This was my favorite work look of the week, and I may even have to look for a vest of my own (surprisingly comfy in my usually arctic office).

Look #5: My skirt and shoes and Julie's fuchsia shirt
Look #5: My skirt and shoes and Julie's fuchsia shirtEmily Pandise

My last business casual work look was interesting — my roommates both styled this zebra skirt in slightly different ways, and I asked them to combine their ideas for the purposes of the exercise. It’s a skirt my mom picked out (thanks again, Kath!), and I’ve grown to love...when worn with white, black or gray. Julie selected the fuchsia top from her own closet, and everything else is mine. Jenny mandated the subtle earrings and nude lip. At first, I felt like the inside of a Crayola box, but as the day wore on, I grew to like it more and more. Maybe I can wear colors that aren’t navy, black or the occasional olive green!

Look #6: Jenny’s earrings, Julie’s shirt and my jeans and shoes.
Look #6: Jenny’s earrings, Julie’s shirt and my jeans and shoes.Emily Pandise

Finally, I slipped in a casual look at work — Jenny’s earrings, Julie’s shirt and my jeans and shoes. This top exemplifies Julie’s love of tasteful embellishment, but is not something I’d really go for. The longer earrings and heels felt like a little much for work, and I usually avoid v-necks to avoid drawing attention to my upper body — but, as the day wore on, I realized that I was paying more attention to my clothes than anyone else. I was into the gold makeup per Julie’s direction, and it was fun to really feel like I was in a Julie costume more than anything else.

Look #7: My clothes, styled a completely different way
Look #7: My clothes, styled a completely different wayEmily Pandise

On Tuesday night, I had a first date with someone I’d met through an app. Jenny dressed my in my own clothes — jumpsuit, denim jacket, earrings and heels — but not in the way I’d usually style them. This outfit was the one I felt most anxious in — it felt weird to be meeting someone for the first time in something I wasn’t super comfortable in. We were grabbing a casual bite, and I was making excuses for myself to bail the whole time I was getting ready — I’m overdressed, it’s raining and the walk is too far to do in heels, etc — and came really close to jumping ship on the no-veto rule. After taking the photo and a deep breath, I realized that my clothes don’t really change me. If I act like I have the confidence to pull off a jumpsuit and block heel at a coffee shop, I will have the confidence to do it. Ultimately, I ended up feeling pretty good in this, even though it was tough to get out of the house and stop overthinking. I felt like this outfit proved my hypothesis — sometimes, all it takes is a new perspective and the support of a friend to feel a little better in the clothes you already have.

Sometimes, all it takes is a new perspective and the support of a friend to feel a little better in the clothes you already have.

Look #8: Julie’s tank and workout pants
Look #8: Julie’s tank and workout pantsEmily Pandise

Wednesday, I joined a friend to walk her dog in Julie’s tank and workout pants. Julie requested boxer braids to complete the look. My workout clothes are strictly black, white, and gray — I have long subscribed to that hard-to-escape “only wear black because it’s slimming” rule. These pants were not too bright, and the green was a fun little pop of color. Not sure if I felt comfortable enough to buy for myself, but it’s further proof that our mothers’ style rules are often wrong.

Look #9: Julie's jumpsuit and leather jacket
Look #9: Julie's jumpsuit and leather jacketEmily Pandise

Thursday night, I went to a networking event, and Julie put me in a jumpsuit and leather jacket of hers, and my evil-eye earrings and sandals. She also mandated a top knot — not a look I usually go for. I got myself into the jumpsuit, threw on a berry lip and spent a solid 20 minutes putting up and taking down my hair before finding a bun-making method that didn’t make me look like Pebbles Flintstone (for any inquiring minds — a ponytail and two bobby pins holding a swirl in place). This was another look that I objectively liked a lot but didn’t feel very “me.” As the night wore on, I leaned into it more. The clothes don’t make the person, they simply enhance. It took me six days to realize it, but I was finally more comfortable being put out of my comfort zone.

Look #10: Julie's shirt and my shorts
Look #10: Julie's shirt and my shortsEmily Pandise

For my final look, Jenny and Julie picked something casual for me on my day off. Julie’s shirt, my shorts (again, picked by my mom), a Julie-supervised mini-smoky eye and my choker, which Julie wears way more than I do. I’ve never felt radiantly comfortable in shorts (who does, really?) but this look was cute, perfect for early fall weather, and it was nice to not just wear gym clothes to the grocery store. I felt like all of these things together made me look a lot younger, and I wish I’d had the fashion sense to wear something like this when I was in college. It was good to get out in the world with an intentional style (rather than gym clothes) for a change.

Finding comfort outside my comfort zone

By the end of the week, my hypothesis had proven true. Despite my “boring” wardrobe, my body image issues and my occasional lack of confidence, my friends had fulfilled their mission well, and I definitely have a few new ideas for how to style my own clothes. I want to wear things I look good in and feel comfortable in, rather than feel like I’m wearing a costume of someone else’s personality. But wearing something a little different or out of my comfort zone didn’t need to be scary — it actually ended up being a lot of fun (despite the many bun attempts and minor pre-date panic). Clothes are so personal, and they are important — but they are also simply clothes, and they don’t solely define who you are.

NEXT: How to build a work uniform on a budget

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