Are you gonna invest or not?!
because crashing a yacht is one thing—buying the wrong pants is another.
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I am an incredibly uncultured human. You could probably rattle off your top five greatest movies of all time, and chances are I’ve seen none of them.
So no, I may not have seen The Godfather, Pulp Fiction, or Casablanca, BUT I can recite every single word of Step Brothers.
One of my favorite scenes is when Dale and Brennan pitch their business, Prestige Worldwide, to their dad. They show him a video they filmed on his prized possession: his yacht. The video ends with them crashing said yacht. Their dad is stunned, furious, and completely speechless. Dale, completely unbothered, looks at him and asks, “Are you guys gonna invest or not?”
That line made me think about my wardrobe, not my yacht (kidding, definitely don’t own one). But there are certain wardrobe pieces we hesitate to buy, because... let’s be honest, some items are an investment.
We all have different budgets. Mine isn’t the same as yours, and yours isn’t the same as mine. But I started thinking about what runs through my brain before I hit “checkout” on a pricier wardrobe piece.
I go through a mental checklist. I cannot remember to turn off my straightener, but I do have a perfect memory of every clothing, jewelry, and bag item I own and where I bought it. Call me a magician.
So here’s how I decide if something’s worth the splurge: my Should I Invest? checklist.
Longevity – Is this a style that will last? Or is it going to be old news in a few months? This one’s tricky. I usually do a little research. Something as simple as a quick Google search like “Utility Pants Fall Fashion 2025” can give me all the info I need.
Versatility – Can I picture wearing this with at least five things I already own? Can it work for the office, the weekend, and a night out?
Four-Season Test – Can I style this piece through all four seasons?
No Copycats – Do I already own something really similar?
Creativity Factor – Does this piece allow for different vibes, looks, or moods depending on accessories or styling?
Shoe-Friendly – Can I wear this with multiple shoe styles? (Think: ballet flats, sandals, sneakers, heels.)
Comfort – Is it actually comfortable? My husband stays in his lane when it comes to fashion advice, but his one golden rule is: “If you’re not comfortable, you’re not going to wear it. Just return it.” He’s not wrong.
Does it feel like me? – Sounds cliché, but as we get more in touch with our style and what makes us feel like a gazillion bucks, we start to recognize what pieces genuinely feel like “us.”
As you saw in my last post, I really loved (and you did too!) these utility pants from J.Crew. They were not on sale during the most recent summer promo, but I bit the bullet and added them to cart anyway. Sure, they might go on sale later, but there’s a reason I didn’t hesitate.
These pants checked all the boxes.
So I challenged myself to prove it, to you and to me. PUT MY DAMN MONEY WHERE MY MOUTH IS!!! Let me tell you— my room looked like a tornado blew through it after the try-on session. My four-shirted husband was shook. I had to force myself to stop because it was time to feed my family (ugh, the nerve). BUT, I could’ve kept going. The versatility of these pants is fantastic.
When it comes to these utility pants, THE LIMIT DOES NOT EXIST.
This post isn’t meant to get you to shop all of my links or even buy these specific pants that I love so much (although you won’t regret it (!!!) Scout’s honor).
The point is to empower you to make wardrobe choices that are smart. Pieces with versatility, longevity, creativity, and that little spark that makes getting dressed more fun.
I kept the details of each look simple so you can focus on the style. I’m wearing classic diamond (CZ, duh) stud earrings (skipping my usual bold statement earrings was a huge challenge), a touch of tinted moisturizer, and sunglasses to hide the bags under my eyes.
I linked as many pieces as I could; if something isn’t linked, it’s most likely an older item that’s no longer available.
Lastly, I know my area for improvement is definitely pairing a bag with my looks. Like I’ve mentioned, I’m a “run out of the house with just my wallet and keys” kind of person. I have nice bags; I just like to gamble with fate every day. Very toxic trait.
Let’s play dress-up analysis with these utility pants!
Step 1: Located the pants on the J.Crew website. Really liked them.
Step 2: Checked out J.Crew’s styling suggestion. I loved how they paired the pants with a ruffle tank that happened to be on final sale. Added both to cart, but I can’t check out quite yet if these pants are just a one-trick pony.
Step 3: Check Pinterest and see other ways this type of pant can be styled. Still can’t checkout unless these pants can be worn MULTIPLE ways.
Step 4: Ran through my Should I Invest? checklist. See below!
LONGEVITY
Did some quick research and feel good about what I found. British Vogue featured a similar utility pants vibe in their article “7 Trouser Trends Set to Soar in 2025,” and Who What Wear had a similar take.
Are my pants technically trousers? No.
Do they resemble the looks being styled in these articles? Yes.
Do I like them regardless of what British Vogue and Who What Wear say? That’s a strong yes.
Could I skip this step entirely? Abso-freaking-lutely. But sometimes it helps stop me from making an impulsive purchase just because something’s trendy (and not aligned with my personal style) only to have it rot in my closet six weeks later.
VERSATILITY
I was able to quickly locate at least five pieces in my closet that I could wear with these utility pants. I also made sure they were seasonally versatile, but don’t worry, I didn’t jump ahead to the Four Seasons Test just yet.
For more reading on how to focus on working with pieces of clothing you already own please see our resident Substack fashion-comedian
’ most recent post!
FOUR-SEASON TEST
This is the ultimate test. Can this piece live up to the hype? Can it actually work across all four seasons? Only one way to find out… PROVE IT.
The look third from the left (white lacey cap sleeve top + utility pants) was heavily influenced by
& !
CREATIVITY
Here’s what I discovered when styling these pants:
Pop of red loves this utility green.
Graphic tees instantly make the look more playful. (See
’s most recent post & ’ most recent post for expert opinions on graphic tees)Tying a sweater around the waist (or shoulders) adds just the right touch of effort.
A colorful scarf (!!!) think red, green, orange, blue, or purple adds interest without trying too hard.
High-low styling: pairing a designer bag and ballet flats with a sweatshirt felt modern and cool.
Want casual? Toss on a denim shirt jacket and a baseball cap and you’re done.
The length of pants is critical, IMO. If the crop doesn’t fall just right and makes wearing boots feel awkward— it’s an immediate NO. But I was pleasantly surprised when I tried them on with suede western boots… and they still looked cute! A rare and welcome win.
COMFORT
The pants had to pass the “Can I chase and catch a runaway dog?” test. I have this strange but very real ability to find dogs that go missing. Don’t ask. It’s a gift. So naturally, I have to be ready at all times—just in case fate calls on me to sprint after a rogue golden retriever.
I ran the test. These pants passed. With flying colors.
DOES IT FEEL LIKE “ME”?
This last one is really the most important. Do these pants feel like me? Do they make me look good, feel confident, and bring out my best self? And the answer is a resounding YES!!
Step 4: Continued to checkout, baby! Followed by immediate dopamine hit, kidding… sorta.
So now I’m asking you—ARE YOU GONNA INVEST OR NOT!?
I hope this helps make your next investment feel a little less scary and a lot more fun. And if you’re a Step Brothers fan, my four-shirted husband made a great joke comparing the Nordstrom Sale to the Catalina Wine Mixer. <Insert courtesy laugh>
Let’s Chat:
What’s one wardrobe investment you made that you never regretted?
Do you have a “should I invest?” checklist? If so, what’s your #1 dealbreaker?
Would you like to see more posts where I take one piece and style it different ways?
Stay golden xo,
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You’re really funny, Traci! (So you agree—you think you’re funny?) I love the framework of course, but what I really wanna talk about now is top 5 movies (and what that even means).
Thanks for the shoutout! 😉
THIS IS GOLD. the creativity! the humor! I'm obsessed. also, my husband and I are constantly yelling "are you gonna invest or not?!" across rooms LOL