Preppy fall outfits – 16 outfits channeling old money aesthetic

What to wear to look bookish fall 2023

Fall has arrived. The air is cold and crisp, the leaves shift color and the whole world takes on an atmosphere of prep schools and New England. There is a back-to-school mentality and you are ready for new beginnings. Preppy style is perfect for fall. Dress in your best preppy outfit and you will look smart, sophisticated, and a little bit sexy. Take a look at these 16 preppy fall outfits and see which one you like the best.

Corduroy skirt + White shirt + Cozy sweater + Camel coat

Here we take 4 classic preppy clothing items and combine them into one epic preppy outfit. Investing in a white shirt and a camel coat will make your whole wardrobe look more preppy. A short skirt brings that bookish sex appeal that is synonymous with preppy style.

Striped shirt + Grey slacks + Trenchcoat + Pearl earrings

Getting a trenchcoat is another easy way to embrace your preppy side. This item looks especially good paired with a striped shirt and a pair of grey slacks.

Don’t forget your pearl earrings. They are the icing on the cake for any preppy outfit.

White jeans + Stripe top + Down vest + Peacoat

Preppy style is also about sport and sport-influenced fashion. Preppy people like sailing, tennis and lacrosse. Do sign up for sailing lessons and dress the part.

White jeans are always part of the preppy uniform. For fall, add a navy peacoat and a down vest.

Jeans + V-neck cashmere sweater + Shirt + Blazer

Are you wondering how to wear your jeans, but still look like old money? The easiest way is to combine a shirt with a v-neck sweater.

A tweed blazer is always a good idea when you create a preppy fall wardrobe. I also especially like expensive-looking accessories for that posh, but down-to-earth, preppy aesthetic, so do bring on the gold. You’ve got the cash.

Dark wash denim + Cream sweater + Green jacket + Plaid scarf

Rich people like to spend time in the countryside, they hunt and get drunk on expensive whisky. Even if you don’t have a countryside estate, you can still look the part.

A pair of dark blue jeans is a good starting point for a preppy fall outfit, add a Barbour jacket and a pair of wellies. The cream sweater serves as a nice contrast.

Cable knit sweater + White pants + Cognac accessories

Cable knit anything is another preppy fall staple. Make sure you get your dose.

Here I give you a fresh and expensive look by combining the sweater with a pair of striped pants. You could also try it with white jeans.

Nothing looks more like money than cognac accessories, make sure you get those.

Grey sweater + White shirt + Blazer + Classic jeans

Here is another version of one of the most classic preppy fall outfits, this time, we use a grey crew neck sweater (preferably in cashmere.)

This item is a staple when you want to build your own preppy outfits.

I especially like the jeans and sunglasses in this look. Don’t forget to bring a chain bag to complete the look. YSL always does the trick.

Feminine blouse + Sweater vest + Plaid skirt + Over-the-knee boots

There are lots of classic fall preppy items in this look. They are all expertly combined into one epic fall outfit.

Sweater vests are a big trend this fall, so you should be able to pick one up.

Combine it with a plaid skirt and a feminine blouse and you will ooze old money. Get a hairband and channel Blair Waldorf, one of the biggest preppy icons of all time.

Brown turtleneck + Burberry skirt + Camel blazer + Loafers

A camel blazer is another important component when you are looking to create preppy fall outfits. A short skirt looks especially dark academia when combined with a chocolate brown turtleneck.

A pair of loafers is almost a must for looking like a member of a prep school.

Cable knit cardigan + White polo shirt + Dark blue jeans + Riding boots

Rich people also like their horses. Adding a pair of riding-inspired boots to your fall wardrobe will have you channeling old money aesthetic.

Ralph Lauren has been churning out preppy staples for 30 years. Make sure you invest in his well-made clothes this fall. (They are easy to find in second-hand stores.)

Trendy and casual fall outfits

If you need some stylish casual outfits, check out my article 24 trendy and casual fall outfits for fall 2024.

Navy blazer + White silk blouse + Tweed skirt + Riding boots

Here we see a pair of black riding boots expertly paired with a tweed skirt. Adding a silk scarf and a navy blazer makes this outfit an instant hit.

A navy blazer will make you look like you are going to the club for a couple of martinis (country club, not night club. forget about night clubs.) Even if your real destination is the nearest Starbucks.

Plaid skirt + Brown silk blouse + Loafers

Another great match for your loafers is a short plaid skirt. I especially like to add a rich silk blouse to create a posh outfit. Grab your Chanel bag and meet your friend for brunch.

Yes, do wear a pair of cashmere socks with your loafers.

Brown corduroy pants + Scarf jacket +Tweed blazer + Silk blouse

This is probably an old Ralph Lauren ad, it is a perfect inspiration for creating preppy fall outfits. Mix and match tweed with corduroy with rich earthy tones. Add a dash of camel and you are ready for a long weekend in the countryside.

Drive your Cabriolet. walk your dogs, plot to murder your friends, and have cocktails in front of the fireplace. All while looking preppy and stylish.

Long dress + Tweed blazer + Floppy hat + Desert boots

Dresses can be preppy as well, especially if they are combined with your tweed blazer. Mix feminine and masculine into this very cool and chic outfit. Loafers or riding boots would work equally great.

Rugby shirt + Tweed pants + Saddle bag

Here we take two classic preppy fall items and combine them into an unexpected outfit.

I particularly like the addition of a saddle bag. Perfection doesn’t need to be complicated.

Poncho + Leather pants

Rich people do occasionally bring out their leather pants, they especially like to combine those pants with a good old posh poncho. You can tell that this girl is standing outside her stable, she clearly has enough money to keep horses.

For the rest of us, we can always look the part by adding enough cognac colors to our outfits.

8 Preppy fall staples for the fall of 2023

Are you wondering how to create amazing preppy fall outfits, while still staying on trend for fall 2023? Look no further than these 15 preppy staples.

1. A cashmere polo sweater is both casual and preppy, and works with most other items.
2. A navy blazer will look especially preppy with gold buttons. You can always replace existing buttons to create an even preppier look.
3. Don’t underestimate the power of a scarf sweater. Yes, you will stand out. But you will look like you have a lot of responsible income.
4. The easiest (and cheapest way) to create a preppy outfit is a plaid scarf.
5. This might be one of the preppiest fall items you can possibly get. So make sure you get a pleated skirt.
6. A camel blazer is simply a must.
7. Preppy outfits are all about the right accessories. A duffel bag for your gym clothes, or your next overnight trip, will make you look like you are on your way to Harward.
8. A bucket bag is a preppy accessory that’s often overlooked, so I had to mention it. Find one second-hand and pretend you found it in your aunt’s attic.

7 more Preppy fall staples for the fall of 2023

1. Another easy styling trick. favored by Blair Waldorf, is to simply add a beret. Her style is, generally speaking, a source of great inspiration for preppy fall outfits.
2. A sweater vest is a big trend for fall 2023. Jump on this trend and all your outfits will look preppy, guaranteed.
3. I love a good peacoat. Black, red or navy, or cream? Any color is good.
4. A tweed jacket that reminds you of a classic lady Chanel jacket, is an excellent way of making your existing outfit into a preppy dream.
5. A short plaid skirt is part of any preppy capsule wardrobe. This one in gingham will look great with just about anything else in your closet.
6. Don’t forget about the classic ballet flats, they are another big trend for 2023, and they make any outfit look much more preppy.
7. The same is true for a pair of loafers. I especially like these brown crocodile ones. Nothing says old money quite the same as crocodiles, and no, you don’t need the real deal.

A final note on preppy fall outfits

With a few preppy items, you can create a lot of preppy outfits. Only one preppy item, such as a plaid skirt or a navy blazer, can be combined with your normal clothes and instantly give you an air of preppiness.

Looking preppy is about crisp, sporty clothes, often in earth colors such as brown and camel.

If you want more preppy outfit examples, read my guide Preppy summer outfits – 16 outfits channeling old money aesthetic.

Enjoy all fall activities while looking like you stepped out of a New England prep school murder mystery.