top of page
Writer's pictureWhitney Wisdom

This is What Happened When I let my Brother Pick My Outfit


It's really just a matching game.

It’s not really fair. I’d like to think he has a strong grasp of my style because he has seen me more of my 9,687 days of life than anyone else. But, then again, I cannot remember the last time my brother, Brandon bought me clothes or accessories as a gift. He reminded me he has not been featured on Whitney Wisdom Blog since January of Season One. “Okay, this will be fun,” I thought. The task is simple. Root through my wardrobe and select a seasonally appropriate outfit for me to do a photoshoot in.


During the first installment of this series of articles: This is What Happened When I Let My Man Pick My Outfit I had no expectations. Literally zero. That’s what made it so fun! The wondering of, if I opened up my entire closet, what would my boyfriend pick?


This go-around, its family. The pressure is on. First stop: my closet. Lucky for Brandon, I just did a closet cleanse the week prior so the surviving pieces all fit me and all show potential. The main challenge lies in putting the pieces together.


We aren't going to disclose the number of skirt options he had to dig through. For um, privacy reasons.

The layout of my closet made sense to Brandon so we stayed there. Drawers were too intimidating and since I have my clothes folded in stacks it would have been messy to go through. Brandon bypassed the “fancy section” aka dresses and went into skirts. I have all my shorts folded into drawers so shorts were a plan B if he couldn’t find a good skirt pairing. He planned to create the look around one of my many printed skirts since the only guidance I gave was to make it seasonally appropriate. He quoted me back to me saying, “The best compliment is when someone thinks your shirt and skirt are a dress because the pairing is so strong other’s think the two pieces were made for each other.” (Read: Wearable Compliments.)


Check it out!

With a railroad-conductor-inspired indigo skirt as the centerpiece, Brandon narrowed down the top options to two picks. A gauze white cold shoulder top that was on the longer side but would have worked knotted or tucked in or a button-front makeup printed cropped blouse. Since the outfit was for moi, he of course, went for the bolder option. I love print mixing but didn’t know if these two would work until I tried it on. I love the striping on an otherwise standard denim mini skirt!


Next we visited the shoe rack and after much deliberation, Brandon went with denim heels to match back to the root of the look, the skirt. During this selection he said nothing. A hush came over the room and the thought process was not narrated.


I find it interesting Brandon and Pat both picked really fun but, really tall heels.

As per usual, I stepped in for hair, makeup, and accessories. Since the print on the blouse pretty much dictates lengthened lashes and a pink pout, that is what I went with. The skirt and shirt are both a little longer so I did a front tuck to add shape and carefree vibes.


I added my own icing.

My hair has been flat from chlorine so I wanted to give it volume by creating tiers the Y2K way. This also makes the look more weekend and less biz casual. Thin silver hoops always add the oomf you didn't know you needed. To make the pink lips pop more from my shirt I added a baby pink bag. I wish the heels weren’t so tall but they are cute so I’d say he mastered the assignment. Who wants in my closet next?


So...how'd he do?

43 views1 comment

Recent Posts

See All

1 Comment


Frieda Holland
Frieda Holland
Aug 29, 2022

Oh my gosh B dud a good job. That must have been fun. Love it!!

Like
Post: Blog2_Post
bottom of page