How to dress when you want to look wealthy and casual
There is something about summer that always makes me want to dress in a preppy style. The preppy staples, such as shorts and blazers and well-made sports clothes, feel especially fresh in warm weather. Take a look at these 16 preppy summer outfits and you will know what to wear on your next brunch date.
Tennis anyone?
Tailored shorts + Blazer + Silk blouse
Light-colored clothes always end up looking preppy. The shades don’t have to match. You can mix white with beige and get a good posh result. This outfit is suitable for running errands followed by lunch at an upscale restaurant.
Fall preppy outfits
Now the seasons have shifted and it is time for fall clothes, make sure you read my article Preppy fall outfits – 16 outfits channeling old money aesthetic.
Grey college sweater + White polo shirt + Black skirt + Gold watch
Preppy style is about being sporty and casual, while still looking expensive. No single piece of clothing achieves this ideal more than a simple polo shirt. Get a white one and you will instantly elevate all your outfits. A grey college sweater is another good idea.
The preppy style was born at the elite universities in the US, so do pretend that you are a student at one of those. And don’t forget your inherited gold watch.
Harward anyone?
Black tank top + Full skirt + Straw accessories
Here I wanted to show a more feminine take on preppy style. Looking like you are on holiday in the Hamptons. It always works. Accessories with whatever you picked up on your Europen tour.
If you want more French summer looks, check out my article How to create perfect French summer outfits.
Gingham printed dress + Pink cardigan
If you are wondering how to look more preppy this summer, I recommend getting one or two pieces of clothing in gingham print.
Another fast way to take your current wardrobe and inject a dose of preppy is to get a pink cardigan. All your outfits will instantly look like “old money.”
Secondhand stores are great places to look for these kinds of clothes. Not even rich people like to spend money when it’s not necessary.
White shirt + knitted pullover + Tailored shorts + Cap
I had to include this fashion shot since it is such a perfect example of a preppy style.
When wearing this look in daily life, you might want to add a pair of shorts.
Putting a shirt under a sweater is a classic preppy styling trick. The cap keeps the outfit from looking too serious. The result is preppy perfection.
Colorful shorts + short-sleeved shirt
Preppy fashion is also about embracing color. There is no better way to do this than to get yourself a pair of colorful shorts. Just pick your favorite color, yellow or pink. Red would also work. Add a short-sleeved shirt, and you will look like you are on your way to “lunch at the country club.”
A Ralph Lauren polo shirt in light pink is another way to ensure that you look as preppy as possible. Ralph Lauren is possibly the biggest preppy brand of them all.
Check out some old Ralph Lauren ads to get the hang of it.
White jeans + Colourful cable knitted sweater
The same outfit combination can be used reversed, color on the top and white on the bottom.
White jeans, and white pants in general, are very “old money aesthetic.” Especially when combined with colors.
Adding a silk scarf is another foolproof trick to look like you spend your summers in the Hamptons.
Tennis skirt + Cable knitted cotton sweater
Rich people do a lot of posh sports. For example, golf, tennis and sailing. They are not afraid to inject a huge dose of sports clothes into their day-to-day outfits.
Also, note how combining navy with white instantly looks posh.
The trick to not look like you just came from the gym is to add accessories such as pearl earrings.
White shirt + Pink shorts
Now when you’ve got your colorful shorts, don’t forget to combine them with your white shirt. A pair of loafers ties the look together.
White shorts + Blue shirt
I hope you also got a pair of white shorts (not in denim).
There is something incredible preppy about an Oxford blue shirt. You look like a Yale University student from the 50s in the best possible way.
Keep things modern by adding a Gucci belt. Rich people are not fans of big, flashy logos, but I think you can get away with this stylish logo.
Any belt is a good idea to look more preppy.
If you have a white shirt, check out my article 15 white shirt outfit ideas for summer.
Shirt dress + Gold jewellery + Espadrilles
If you are looking for more feminine ways of being preppy, look no further than the shirt dress.
This easy look is one of the best preppy summer outfits. Just add a pair of sunglasses and some discreet bling.
White jeans + striped top + Navy blazer
Another sailing shoot. You do really need a sailing course. Preppy people also like to read. Being preppy is not only about style, it is also about what you know. A preppy person will know their literature.
A navy blazer is another great buy if you want to create your own preppy outfits.
Take note of the belt and the discreet jewelry.
Black top + Beige skirt
Here is another more feminine preppy look. Beige is such a preppy color, especially suitable for summer.
Her top is a bit “too much,” but I guess even preppy people need to bring their sex appeal from time to time.
This would be a great look for a candlelight dinner.
I added a jacket in case you get cold. The skirt is Max Mara, another great brand for preppy styles.
Wimbledon Sweater + Tennis skirt
While doing research for this post, I discovered that Wimbledon has its own shop with lots of cute preppy accessories. Or why not book tickets to the next tournament?
White canvas shoes are another staple when you are looking to create preppy summer outfits.
Cable knitted navy polo + white tailored shorts + Adidas shoes
I keep coming back to cable knitted sweaters, I guess you need to get one. They just look so much preppier than regular sweaters.
This look, once again, shows the preppy power of navy and white.
A high ponytail must be the preppiest way to style your hair.
Argyle sweater + Tennis skirt + Headband
Argyle is another preppy favorite; you often see this pattern in golf clothes. Lacoste is a good preppy brand.
Top it all off with a headband and you are ready for any posh situation.
A final note on preppy summer outfits
You only need a few things to take an ordinary outfit and turn it into a preppy outfit. Many of those things can be found in second-hand shops.
Since many of the preppy brands are expensive (that’s kind of the whole point,) I recommend searching for those special items in second-hand shops.
Moa Ailert is the founder and editor-in-chief of Her Brilliant Friend.
She has a bachelor’s degree in philosophy and plenty of insight into human psychology from traveling and living in different places around the world.
Moa is currently based in Portugal where she has a guesthouse; Villa dos Irmaos.
She has various websites, among others Ericeira Insider, but Her brilliant friend is her true passion project.
