Sometimes your best friend is your mirror image. And sometimes, the two of you couldn't be more different.
That's Jess Torres and I. We're best friends and coworkers — but even though we occasionally dress alike, our personal styles are WILDLY different.
So we decided to dress one another to push each other's style boundaries — and prove that there's NO fashion rule that can't be broken.
First, there's me. I describe my style as "luxurious witch." I like black clothing... and that's about it. Think: Jessica Jones if she woke up and started working in fashion.
I wear some variation of black jeans, a black T-shirt, pointy black boots, and my leather jacket nearly every day. I don't take a lot of fashion risks, because I've found what I like to wear and I stick to it. I don't wear color unless I'm forced to, and the more shapeless or aggressively ugly a piece of clothing is, the more I'll like it.
I stay away from clothing that's too "cute" or "sexy." I really hope that Jess doesn't put me in pink, but I have a horrible feeling that she will.
Jess Torres describes her everyday style as ANYTHING GOES. "I spent years feeling like I needed to hide my body," she said. "Now I wear whatever I want."
"I love crop tops, over the top accessories, and anything that's loud and obnoxious," she says. "I like showing off how I look. I don't like anything that's too shapeless or like a mom would wear, because that's what I was always told I had to put on to hide myself. I also don't wear a lot of really sexy, revealing stuff — I'm still a little uncomfortable being 'hot.'"
The first outfit that I styled for Jess combines a few of her fashion fears — tapered pants, sheer mesh, and a long suit jacket.
I knew that Jess would never, ever wear a business goth outfit — so that's what I put her in. I wanted everything to be very sleek and streamlined, with little hints of trends that I've been wanting her to try. I was especially excited about the Universal Standard jacket ($230, Nordstrom), which was the PERFECT combination of cool business bitch.
"I haven't worn a blazer like this since I was a kid," said Jess. "Plus-size office clothing is usually so dated and ugly. This jacket is really cute, and it's really warm — I'd wear this in winter for sure!"
"This sheer shirt made me SO nervous," said Jess. "But the second I put it on, I was ready to go to a business meeting at 4 and be a ho at 5. Alle really gets me."
"I've been avoiding pants with the tie-waist and tapered legs because I didn't think they'd look good on my body," said Jess. "But these are BOMB."
Jess is wearing ASOS curve peg pants with woven tie ($40, ASOS) in a size 20, "These fit really well, even with my fuller belly. I also really like that these have pockets, and I LOVE this tie-waist! It's a little bit of a change for me — I never would have picked these out by myself, but they're bomb."
"When Alle showed me these shoes, I thought she was joking," said Jess. "I thought I would hate them, but they're adorable."
Sometimes I just see things and I KNOW that I need them for Jess. I've never seen Jess wear ANYTHING like these Shiraz pointed heels ($48, ASOS), but in my heart I knew that she needed them with this outfit.
Jess needed a little more convincing. "These were pretty comfortable, and I liked the pointed cut out that matched the toe," she said. "They're really '90s, but I like them. I'm glad Alle pushed me."
The first outfit that Jess styled for me was this. It was VERY different than anything I'd ever wear, and it forced me to face a lot of my fashion fears.
This is a LOT for me — and according to Jess, that was the point. "Alle never does wild accessories, so I wanted to put her in a bright red beret and give her a crazy bag," said Jess. "I think that Alle avoids trends or things that will make her stand out, so I gave her all the trendy clothes at once."
I was completely convinced that I'd *hate* this beret — but I honestly didn't.
"Berets are my THING this season," said Jess. "So when I saw this red beret ($16, ASOS), I needed to make Alle wear it. She'd never wear it, but I LOVE her in red."
I do *not* love me in bright red. But this beret didn't make me want to die, which was surprising. I've been out of the ornamental hat game for such a long time, I thought I'd look like a military clown... but it was pretty cute!
"Alle has this asymmetrical white T-shirt that I REALLY love — but she's only worn it once," said Jess.
This is a collab that designer Cedric Charlier did with Fruit of the Loom. I like this shirt very much, but I'm scared to wear it because it's so cool... and down in my heart I don't think I'm a very cool person. Jess forcing me to wear it kind of forced me to admit that I'm awesome, and I can take non-classic fashion risks.
Jess knows I avoid "Instagram fashion trends" at all costs, so she put me in RIPPED BUTT MOM JEANS.
"I originally wanted to put her in these ripped bum jeans ($56, ASOS) in faded light blue — something else she'd never wear," said Jess. "But ASOS was sold out, so she got the dark gray. I thought these looked amazing on her, I wish she'd wear them every day."
While I don't think these pants looked *bad* or anything, they're not something I could wear to the office. The actual underside of my butt was almost visible through these rips, and that's a level of exposure I need to work up to.
Jess and I both realized that styling another person — and forcing them to expand their style boundaries — is harder than it looks. "I feel like we turned into each other with these looks," said Jess.
"I'd 100% wear this," said Jess. "But I can also see Alle wearing my outfit, too. I feel like I'm wearing a bit of her confidence in this — she'd wear a sheer shirt, so why can't I?"
As for me, I liked my outfit, even as I didn't feel like myself. I was also roundly roasted for it in the office — someone who shall remain nameless told me that I looked like an off-duty Urban Outfitters model. THAT'S WAY HARSH, TAI.
For Jess' next outfit, I picked three things I knew about her style and pushed — she doesn't wear drape-y, shapeless clothing, she doesn't do clunky shoes, and she's NEVER worn purple.
"I was so nervous about this dress," said Jess. "When Alle pulled this off the rack in the studio, my heart sunk. I've never worn purple — when I was younger, I didn't want to look like Barney. I thought I would because I was so big."
I'd been on the lookout for a casual, bright purple dress for my girl for a few months now, and finally found this midi dress on sale ($32, ASOS), I JUMPED at it.
"I liked this casual dress with these angular sunglasses," said Jess. "Balancing the purple with the black made me feel more confident."
Jess' second outfit also pushed me in REALLY serious ways. Hello, drape-y millennial pink dress worn over sheer top!
Wearing color makes me feel vulnerable. But this dress had enough tough details to keep me from feeling like a total fraud... and I was honestly very into the sheer shirt.
I would have never, ever picked out a striped mesh crop top ($29, ASOS) to wear under a pink slip dress at 33. Looking at this outfit made me feel like I was playing dress up — but according to Jess, that was the point. "I knew you'd never wear pink on your own," she said. "And maybe you won't wear it again, but I wanted you to know that you COULD."
Jess finished my outfit with a pair of rose quartz cat eye sunglasses that she got from a street vendor. "Alle and I both love sunglasses," she said. "It was fun to make her wear a pair that's more my style than hers."
We didn't plan to trade shades — that's just what happens when you spend 50 hours a week with someone.
Overall, our second outfits really pushed and challenged us in ways that we weren't expecting.
"I love my body," said Jess. "But when I wore that purple dress, I realized how some of the things I used to worry about when I was younger still affect my self-image. Alle's outfit showed me that I don't have to let those things bother me. There's still a lot of fashion challenges for me to take!"
As for me, I don't think I'll magically transform into a pastel pink kind of girl — but I did realize that my fashion rules, which do protect me, can also be limiting. Risks are scary, but sometimes feeling vulnerable is worth it.
For her final outfit, I put Jess in a super hot rose dress. I know she's more comfortable in "cute" clothes (which is 100% fine), but I wanted to push her out of her comfort zone.
"I don't usually see myself as sexy," said Jess. "That's something that I'm working on. A dress like this that's strapless and really out there makes me feel like I'm putting myself out for too much attention. But I deserve attention!"
I chose this City Chic dolce rose dress ($170, Nordstrom) because Jess looks awesome in red. Jess is in a size 20, but says that women with bigger busts or fuller bellies should size up.
"I was worried about this dress," said Jess. "I'd never pick something like this out, but I'm glad that Alle did. It showed me how she sees me — that I'm beautiful and sexy the way I am."
"You don't have to wait until you lose weight or change your body to be sexy," said Jess. "You're sexy right now. That's what this dress reminded me of."
Meanwhile, Jess styled me in something that combined all of my biggest emotional stumbling blocks: HOT PINK SKIRT-SUIT WITH VISIBLE BRA.
"Alle hates pink," said Jess. "I wanted to work up to this outfit with that lighter pink dress, then push her all the way out there with this look. I was inspired by Hillary Banks from "Fresh Prince." This is a double-breasted blazer ($80, ASOS) and uber high-waisted skirt ($45, ASOS). The skirt is very true to size, but the blazer runs VERY large — you may want to consider sizing down.
"Alle picks clothes that cover her up," said Jess. "I wanted her to wear this blazer unbuttoned to completely show her bralette, but it was a lot."
This suit was so bright, you could see me from space. Just putting the blazer on made me feel like I was being pushed out of a spaceship into the cold depths of the void, THAT'S how far out of my comfort zone it was.
But Jess doesn't challenge me unless there's something that I need to learn. I realized that I felt vulnerable in this outfit because, on some level, I don't want to be seen to deliberately attract attention — something you can't help but do when you're nearly six feet tall and dressed in neon pink.
While I don't think my all-black uniform is anything other than an expression of who I am and how I want to be seen, there's really nothing like a high-waisted miniskirt and visible bra to remind you that COLOR MAKES PEOPLE STARE AT YOU. This outfit was a really valuable fashion lesson from Jess to me.
"I think these last outfits were about how we see ourselves, versus how we see each other," said Jess. "I see Alle as someone who isn't afraid to be the center of attention, and she sees me as someone really beautiful. The looks we styled for each other reflect that."
No matter where you are on your self-love journey, sometimes it's hard to see yourself the way the rest of the world sees you.
And sometimes you have a friend who's willing to take you all the way out of your fashion comfort zone and remind you of all the ways you're really awesome. I'm really lucky to have that in Jess.
So at the end of our style experiment, what did we learn?
We learned that styling someone else, no matter how well you know them, is HARD.
We learned that, no matter who you are, there are always fashion boundaries to be pushed. Style rules, even the ones you make for yourself, are there to be broken — and breaking those rules can be fun!
We learned that personal style isn't a size, or a color, or a silhouette. It's about bringing your own brand of confidence to whatever you have on.