There’s something about classic preppy style that never really goes away.
Sure, trends come and go. One minute everyone is dressing like they’re headed to the gym, and the next minute we’re all pretending we casually own linen pants and sailboats 😅
But some looks?
👉 They just last.
And lately, I’ve noticed two classic styles making a huge comeback:
- The rugby shirt look
- The cricket sweater look
Honestly…I’m fully here for it.
Why Classic Sports Style Always Works
A lot of preppy fashion actually comes from old-school sports style.
Think:
- Tennis
- Rugby
- Cricket
- Rowing
- Golf
These looks were built around:
👉 Clean lines
👉 Layering
👉 Timeless colors
👉 And clothes that somehow look relaxed and put together at the same time
That’s why brands like Ralph Lauren, Brooks Brothers, J.Crew, and Vineyard Vines have leaned into these styles for years.
The good news?
👉 You absolutely do not have to spend designer prices to pull this off.
The Rugby Shirt Look: Casual But Somehow Fancy
I don’t know how rugby shirts manage to do this, but they somehow make you look:
- Sporty
- Preppy
- Relaxed
- And slightly like you summer in Nantucket
All at once.
The oversized striped rugby shirt paired with:
- Khakis
- A classic sneaker
- Maybe even a blazer if you’re feeling bold
…is one of the easiest ways to elevate casual style without trying too hard.
And the best part?
You can find affordable rugby shirts almost everywhere right now.
A few things I love about this look:
- Easy to layer
- Works for spring and fall
- Looks good dressed up or down
- Comfortable enough to actually wear all day
Which, as a dad, matters a lot more than it used to 😅
The Cricket Sweater Look: Peak Classic Preppy Style
Now let’s talk about the cricket sweater.
This might be one of the most timeless looks ever.
The cable knit texture, the striped neckline, the vintage athletic vibe—it somehow feels:
👉 Old money
👉 Country club
👉 Tennis match in 1987
…and I mean all of that in the best way possible.
What I love most about the cricket sweater trend is that it works with:
- Shorts
- Chinos
- Denim
- Even over a button down
And while some designer versions cost hundreds of dollars…
👉 You can recreate this entire aesthetic for way less.
That’s kind of the whole point of this series:
Finding the look without needing the luxury price tag.
Style Doesn’t Have to Be Expensive
I think one of the biggest misconceptions with preppy style is that you have to spend a fortune.
You don’t.
Honestly, a lot of it comes down to:
- Fit
- Color palette
- Classic pieces
- Confidence
You can build a great wardrobe by mixing:
- Affordable basics
- Vintage-inspired pieces
- And one or two “statement” items you really love
And personally?
I’d rather spend less and still get the vibe right.
Especially when four kids are eating me out of house and home 😅
The Modern Dad Take
These looks are exactly why I started this series.
I love:
- Classic menswear
- Preppy style
- Vintage athletic inspiration
- And outfits that feel timeless instead of trendy
But I also live in the real world where:
👉 mortgages exist
👉 kids need shoes every 14 minutes
👉 and nobody needs a $600 sweater
So if I can recreate the same aesthetic at a fraction of the cost?
That’s the win.
Final Thoughts
If you’ve been wanting to level up your style a little, these are two easy places to start:
- Rugby shirts
- Cricket sweaters
Classic. Timeless. Easy to wear.
And the best part?
You can absolutely make these looks work without breaking the bank.
Which honestly feels very Modern Dad.
