Jackie Howard wore so many cool outfits in My Life with the Walter Boys, that it’s hard to keep up with her wardrobe choices.
As many of those who watched the show will probably already know, Jackie moves to Colorado to live with the Walter family after her mother and sister tragically passed away.
With hopes of attending an Ivy League college, the teenager finds it challenging to adapt to small-town life after leaving the bustling city of New York.
Along with the way Jackie also finds herself caught in a love triangle with Alex and Cole, each pulling her in different directions.

But now let’s talk about Jackie’s fashion choices because let’s face it we’re all a bit envious of her style. She is often seen rocking preppy styles and wearing other clothing items, which include pops of pink. From blazers to dresses, her outfits always stand out.
Preppy Outfits
We all know Jackie is super smart, and even though her school doesn’t have a strict dress code, she often wears preppy outfits. She rocks cardigans, plaid shirts, sweaters, sweater vests, and brogues – which are all pieces that fit her style perfectly.
Here’s some outfit inspiration that’s budget-friendly and totally match her aesthetic.







Pretty in Pink
Throughout the show, Jackie wears some elements of pink in her outfits whether it’s her jumpers or coats.
In My Life with the Walter Boys, the straight-A student navigates a new relationship after settling into a completely different state. Everything is new, including her living situation and room. But thankfully, what Jackie gets to keep are her old pictures from her past life and her belongings, including her comfort clothes.
Here are just some outfits that I know she would totally rock.



Jackie Howard’s Perfect Outdoor Wear
After moving to rural Colorado, Jackie spends most of her days outside whether it’s going to the lake with Cole or watching Alex horse riding. However, because of the chilly weather, the teen has no other choice but to pull on her coziest coats and sweaters – and there very stylist!



Go-To Summery Dresses
Her summer dresses are lush. Whether it’s a flowy floral dress or a simple, chic sundress, she knows how to keep cool while looking put together.

These dresses show off her fun, laid-back side while still maintaining that preppy vibe she’s known for. Paired with simple accessories or a cute pair of sandals, Jackie’s summer outfits are the perfect go-to for warm-weather days.



Must-Have Cardigans for Every Occasion

Ok, another thing we have to talk about is Jackie’s awesome cardigan choices. Her purple cardigan really stood out for me as it screams I want to dress feminine whilst also going for a preppy and put-together look.
This particular scene showed Jackie in her element as she tried to sign up for as many extracurricular activities as possible to impress the admissions officers on her college applications.


Jackie Howard’s Sleeveless Summer Tops

There are so many outfits she wore, that it’s hard to keep count. However, I was particularly envious of the blue sleeveless top she wore. You remember – the scenes where she went out with Cole as they rode horses? Yep, that’s the one. If you want to find your perfect Jackie-inspired summer top, then look no further.


If you loved reading this post, check out a ranking of My Life with the Walter Boys season 1!