Boyfriend Picks My Outfit Challenge—Fashion Editor Edition – Fashion Trends & Style Advice

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In our eyes, there are two radically different ways to approach getting dressed—dressing for yourself, and dressing for others. Most days, STYLECASTER’s Fashion Team prefers the former, but in the words of Carrie Bradshaw, we couldn’t help but wonder…what would our OOTD posts look like if our boyfriends were the ones picking the outfits?

In honor of Valentine’s Day and boyfriends everywhere waiting patiently for their girlfriends to pick out the right dress, we’ve given Brian and Pat full control of our wardrobes for not one, not two, but three fictitious date nights. And hey, if we like their selections, maybe we’ll wear them on actual date nights!

Dressing to appease others is never the move, but seeing how a fresh set of eyes approached our closets actually got our creative juices flowing. Suddenly, the sartorial options seemed endless! And while neither boyfriend will be giving Law Roach or Maeve Reilly a run for their money anytime soon, we’d say they did a pretty good job at playing stylist for the day.

Without further ado, check out the good, the bad, and the why-didn’t-we-think-of-that below.

Pat’s First Outfit For Bella: B for Basic

The Look: Central Park West Cut-Out Sweater, American Eagle Jeans, Steve Madden Boots, Freja Bag

Pat’s Vision: This is a standard outfit. Everyone needs a pair of jeans in their wardrobe. Black is a good color to wear out at night. So, this is a safe first outfit pick.

Bella’s Critique: As someone who hasn’t worn a simple black-sweater-and-denim combo in years, this felt super basic. But I really do love these American Eagle jeans, so this was a good reminder to wear them more.

Brian’s First Outfit for Olivia: Roses are Red, Date Night is Blue

The Look: Mango Blazer, Zara Top, 1 People Blazer, Mango Heels, Balenciaga Bag

Brian’s Vision: I like the color blue and think this shirt looks nice on Olivia. I basically just picked out everything blue in her closet and put it all together. The blazer made it fancy so I added heels.

Olivia’s Critique: I am really excited that Brian put together this look because it is an outfit that completely encapsulates my personal style (and I’m honestly surprised I hadn’t thought of the combination myself yet). My only piece of feedback is that linen pants are a little too cold for February, but I will definitely be wearing this look come spring.

 

Pat’s Second Outfit For Bella: Tiger Stripes

The Look: AFRM Dress, Steve Madden Boots, Prada Cleo Bag

Pat’s Vision: Long dresses are for classier dates, which is the best time to wear the Prada bag. The pattern on this dress is better than just a solid dress.

Bella’s Critique: I have tons of these sheer mesh dresses from AFRM and I love them so much, so this outfit was an immediate Yes for me. I’m pretty sure I’ve worn it head to toe before without him knowing, so this is definite proof that he “gets” my taste.

Brian’s Second Outfit for Olivia: Rain Check

The Look: Zara Dress, Nocturne Rain Jacket, Zara Boots, YSL Bag

Brian’s Vision: I liked when Olivia wore this black dress in Mexico so I thought it would be good for a date. It’s too cold to wear a dress right now so I added the rain jacket to be practical.

Olivia’s Critique: I knew this would be an interesting look after Brian held up the strapless black dress and said, “what is this?”. He really went above and beyond my anticipated intrigue by pairing it with a rain jacket. Brian is a rock climber and spends a lot of time outdoors, so I do appreciate his commitment to functional pieces. When I do wear this out, I’ll probably swap the rain jacket for a leather blazer.

Pat’s Third Outfit For Bella: Best in Brown

The Look: Le Lis Wrap-Front Blouse, Princess Polly Skirt, Zara Trench, Steve Madden Boots, Brandon Blackwood Arlen Bag

Pat’s Vision: Brown is a good color on Bella and she looks good in skirts. I’m not sure what else goes with a skirt besides a blouse, so that’s why I picked it. It’s a bonus that her boobs look great in that top.

Bella’s Critique: Other than the cleavage, this feels like more of a meetings outfit than a date night look, but I’d definitely wear this IRL. It wasn’t until he added the leather trench and BB bag that I was sold, though!

Brian’s Third Outfit for Olivia: Man Repeller Reborn

The Look: Vintage Sweater, Vintage Skirt, Lisa Says Gah Jacket, Urban Outfitters Pants, Zara Boots, Bottega Veneta Bag

Brian’s Vision: Corduroy is a cool jacket material and I thought the sweater would look nice. I’ve never seen Olivia wear this skirt before so I thought, why not? I didn’t want her legs to be cold so I added pants (note: Brian was unsure if these were regular pants or pajama pants).

Olivia’s Critique: I’m going to be honest, this outfit caused a little fight because I thought Brian wasn’t taking the assignment seriously. This look is made up entirely of items I never wear from my closet (rough start) and is proportionally unflattering. Even though I think it’s a questionable look, Brian insisted that it was “cute and looked like I had a sense of humor”. Brian better put his money where his mouth is, because I will be wearing this outfit on a date to prove my point.