“And these pants are flowy, but not too flowy that they’ll get stuck in your bike chain,” I say to Anna as she looks in the mirror. I stand back to admire my work.
“Do you hate it?” I ask, feeling my heart rise in my chest.
“No!” Anna exclaims. “I like it!”
I can’t tell if she’s just saying that because she’s my sister and she knows I’ll be upset if I found out the truth.
But the task was to style her with items she’s never worn together, so here we go!
Anna loves being extra. In our circle of friends, she’s known as the risk-taker, always playing the wild card with her choice of clothing for concerts, clubs, fancy restaurants—you name it. And she doesn’t play by the fashion rules. In fact, she makes her own rules. A puffy-sleeved leopard dress with sparkly heels? Yes. Wearing all white after Labor Day? 100% yes.
Once she went barhopping with friends and told them she dressed “casual, but with a flair of sex appeal.” Her friends didn’t know what to expect and were puzzled when she showed up wearing jeans and a men’s button-down.
“What’s so sexy about that?” Brit inquired.
To which Anna responded, “Well, me. DUH!”
So when it came to styling Anna for happy hour after a monotonous day of remote work, I wondered what other rules can I make her break?

I styled her in a sleeveless flamingo pink t-shirt from Pangaia. She’s biking to happy hour and breathable clothing is a must in Sacramento’s heat. This particular cropped shirt is sustainably made out of organic cotton and is guaranteed to keep you cool in the sun. Plus, it’s made with Pangaia’s PPRMINT oil technology that’s meant to keep your shirt crisp and clean for longer, so you could wash it less, making it all the better for the planet.
The trickiest part of the look was picking out the right bottoms, since Anna was biking. We’ve had countless experiences pulling over to free clothing that got stuck in the bike chain while pedaling. So, a pair of polished and flexible trousers from J.Crew were the answer (similar). These trousers are silky to the touch and feature a vibrant elephant print. I added a hot pink blazer (similar) to the look because it matched the trousers’ texture and helps the pink stand out among the slightly muted trousers.
I chose classic white sneakers, since they match with everything. This pair from Sezane has a smooth leather exterior paired with adorable laces that elevates the status of a basic white shoe, especially when worn with sparkly socks.
For accessories, Anna wore simple blue earrings and a long necklace (similar) to bring the outfit together.
As I watched Anna bike off to meet her friend, I saw the mechanics of the outfit rise to the surface. To me, it represents comfortability and functionality without the fear of being “too much.” When you dress without the need to follow a set of fashion principles and instead dress for yourself, that’s when the magic happens.
