Guide Jul 07
Written by Colin Dempsey Read about our editorial guidelines 
Colin Dempsey
Table of Contents
Now that cottagecore is a thing and Wes Anderson’s quirky style has become mainstream, preppiness has taken on a whole new connotation. It’s no longer just lacrosse dudes wearing bright pink Lacoste polos with frosted tips. But it’s also not not that either.
Nowadays, there are more preppy outfit ideas out there than we’ve ever seen before, which is a positive thing for creative minds but a negative thing for people who suffer from option paralysis.
As such, I’ve put together a list of preppy outfit ideas that you can use for inspiration or if you’re looking for any of the following styles:
- Preppy outfit guys
- Preppy girl outfits
- Preppy outfit men’s
- Preppy tennis outfits
- Preppy country club outfits
- Preppy aesthetic outfits
What Makes Up A Preppy Outfit?
Preppy outfit ideas usually include a standard yet interchangeable set of garments. You can add any of the following pieces to your fits and look like your dad owns a yacht:
- Boat shoes
- Blazers
- Khakis or chino pants
- Argyle sweaters
- Loafers
- Derby shoes
- Polos
History Of Preppy Outfits
The term ‘prep’—and all associated preppy outfit ideas—harkens back to the 1950s. The subculture is linked to upperclassmen who attended Ivy League schools and other high-status universities in the American Northeast.
Most preppy fashion comes from these individuals’ interests and pastimes. For instance, sports like polo, rowing, golf, squash, tennis, and rugby all influence preppy fashion.
As can be expected, the style was inherently exclusionary, and only became publicly available in the 1980s when brands like Ralph Lauren and Izod reinvigorated commercial interest in preppy attire.
What Are Some Popular Preppy Outfit Ideas?
Popular preppy outfit ideas include staples like a tucked-in polo shirt, golf pants, and Derbys for men. Women can pair skirts or dresses with sweaters wrapped around their necks and loafers on their feet.
24 Preppy Outfit Ideas
#1:
Preppy outfit ideas like these prove that you can still look intelligent when trying to look like you’re the captain of the rowing team.
This ensemble features many of the core principles of preppy fashion (i.e. lighter colors, khaki pants, leather boots, and Ralph Lauren socks) in a more subtle manner.
#2:
There are also plenty of good preppy outfit ideas that allow you to wear pieces you wouldn’t otherwise be able to style. I’m talking about the matching blazer and skirt in this instance. When paired together, the pattern on these garments would look too tryhard unless you really wanted the preppy vibe.
Thankfully, the thoughtful inclusion of a complementary brown handbag provides some balance to the ensemble. Plus, this outfit is a good blueprint if you have two pieces that match and you’re having trouble building a look around them.
#3:
#4:
#5:
#6:
#7:
#8:
#9:
#10:
#11:
#12:
#13:
#14:
#15:
#16:
#17:
#18:
#19:
#20:
#21:
#22:
#23:
#24:
Fashion Tips To Avoid With Preppy Outfits
Since the preppy style has been the subject of much public ridicule, there are a few things you should avoid with your preppy outfit ideas.
The first, and most obvious, is popped collars—they’re just not relevant anymore. These days, popping your collar will instantly make you look like a caricature.
Another pet peeve of mine is wearing high socks with shorts. High socks can work if you’re wearing a skirt or a dress, but they just look tacky when you pair them with shorts.
Finally, you won’t usually wear black if you want genuine preppy outfit ideas. Navy blue is the go-to dark color and makes for a suitable substitute.
Best Places To Buy Preppy Outfits
The best places to buy preppy outfits carry a long lineage like the Ivy League schools that inspired the aesthetic. That makes it easy for me to recommend some reliable retailers. You should head to these stores if you’re looking into the preppy style:
- Lacoste
- Ralph Lauren
- J. Crew
- Tommy Hilfiger
- Izod
Final Thoughts
Preppy outfit ideas can give you the opportunity to wear brands and styles that you wouldn’t otherwise sport. That’s the biggest appeal of the style these days, as it opens more doors than it closes—which is an ironic twist on its exclusionary background.
Looking for more outfit ideas? We’ve got you covered:
3 Work Outfit Ideas
3 2000s Outfit Ideas
5 Date Night Outfit Ideas
