13 best Preppy winter outfit ideas

This picture shows a variety of preppy winter outfit ideas for men and women.

Especially in the season of winter, preppy outfits have to adapt to change from short and colorful summer outfits to a cozy preppy winter outfit. Therefore, a variety of clothes must be included to keep that preppy appearance. But what are preppy winter outfits?

As a general rule, preppy winter outfits consist of coats, cozy sweaters, skirts and tights, as well as jeans and jackets to prevent the cold from coming catching you. To nevertheless make a stylish appearance, those outfits need to consist of the right fits, materials, and colors.

To get to know more about how to easily put together a preppy winter outfit and some useful tips on how to style them, read on. Additionally, we will feature multiple unique preppy winter outfits for men and women.

3 Tips on how to style preppy winter outfits

Before we start with the outfit inspirations, let’s first take a quick glance at 3 essential tips to put together a preppy winter outfit.

1. Start Layering

This might not come as a surprise to you but layering different garments is very important with the preppy aesthetic in winter. As many items of this aesthetic feature light fabrics, you either can’t wear them in winter or only wear them if you can layer them. As this seems to be the better option, start layering!

Also, you will want to keep the silhouette rather tight. Therefore, ultra baggy clothes and the latest streetwear will not come to play. So, opt for a simple polo or Oxford shirt as a starting layer and add a sweater and coat depending how cold it gets.

2. Choose appropriate bottoms and footwear

Preppy style often features pleated skirts and short pants, especially in summer. In order not to always wear jeans or chinos, try to incorporate a pleated skirt and simply put some tights underneath Also, some leather leggings can look classy and elegant under a cozy sweater and coat.

When it comes to footwear, opt for boots mainly. Those not only prevent your pants from getting soaked by the rain or snow but also make up comfortable and most importantly warm footwear. Alternatively, some elegant sneakers will also work.

For some more infos about preppy shoes, check out my recent article here.

3. Start incorporating colors

As especially in winter, many outfits will look boring and not very colorful, preppy winter outfits can stand out perfectly. By incorporating some colorful blends like a red sweater or a colorful beanie, you will not only create a unique preppy winter outfit but also look fashionable at the same time.

7 preppy winter outfit ideas for women

Let’s start off our list of preppy winter outfits with some inspiration for women.

Classic chic sweater

For the first of preppy winter outfits, you will want to incorporate an Oxford or Polo shirt as a base layer. Additionally, a sweater or sweater vest will make this outfit look great. To round it up, some chinos or tailored pants and a coat will look great. Some Chelsea or riding boots will work perfectly here.

Fluffy leather jacket

This more modern look offers a unique casual preppy appearance for a rich girl look. Ultimately, the leather jacket will be the most noticeable item here. Underneath, you may want to wear a simple long-sleeved shirt or a sweater. For pants, some jeans or chinos will work great as well.

Nautical preppy look

This look represents the otherwise lightweight east coast preppy look you may often see during summer. The basics of nautical stripes and the navy blazer or coat remain the same only that instead of a top, you will now wear a sweater and a coat above. Jeans and some knee-high boots will round up this style.

For some more infos about the east coast preppy style, check out ma recent article here.

Pleated skirt and tights

This look often reminds me of the typical preppy school girl aesthetic. The rather short pleated skirt is now matched with some neutral-colored tights underneath and a cozy top. Also, you may want to add a coat or blazer above for some extra warmth.

Cute dress

Often, you will find this preppy winter outfit in other seasons due to its rather short dress. For winter, an Oxford shirt and some tights underneath will make this outfit suitable for the cold weather. Some boots and a coat will also work perfectly fine here.

Classic jeans outfit

This preppy outfit is the ultimate versatile combination of everything that matches a pair of jeans. From a hoodie or sweater to a long-sleeved shirt, you can really match anything to this outfit. Also, a scarf and coat will look great here.

For some more inspiration on preppy jeans outfits, check out my recent article here.

Elegant preppy winter outfit

Remember when we talked about leggings being the perfect match for an elegant preppy winter outfit? Now, their time has come. With a combination of some leggings or chinos and a nice Oxford shirt and sweater above, this outfit truly looks amazing. If you add a cozy coat and some boots, it will give off an elegant preppy look.

6 Preppy winter outfit ideas for men

After we’ve come across multiple outfits for women, let’s now look at what the preppy style has to offer for men in winter.

For some more inspiration on how to style preppy outfits for men, check out my recent article here.

Schoolboy aesthetic

This elegant combination of a polo or Oxford shirt with a cable knit sweater will make up a unique preppy outfit suited for fall and winter. Additionally, some chinos or tailored pants will look stunning here. For footwear, some boots or elegant sneaker will work perfectly here.

Layered Oxford shirt

This may look similar to the first outfit but here, you will not try to imitate a school uniform. If you layer up an Oxford shirt with a sweater or sweater vest and put on a pair of chinos or khaki pants, it will make a great preppy winter outfit. Also, a coat can be quiet beneficial here.

Masculine cardigan

Usually, a cardigan is an item women often wear. It can make up a pretty nice preppy outfit for men though. You can go for a sporty look by pairing it with a polo shirt and some chinos or opt for a formal appearance with a dress shirt and tie like in this picture. Oxford shoes and loafers will work great here.

Countryside boy

This outfit may just look like it came straight out of an article about old money winter outfits. And whilst this outfit also represents old money, you can find it to be worn in a preppy way as well. Especially with a patterned scarf and a nice cable knit sweater as well as a coat, this outfit suits the preppy aesthetic perfectly. Here, some boots are prefect.

Compare your preppy outfits with some old money winter outfits here.

Formal boarding schooler

This may just be the most formal look on this whole list of preppy winter outfits. Often times those boarding school uniforms can feature some pretty lightweight fabric but you will want to opt for some nice cotton pants and a firm blazer. Additionally, a coat may help to stay warm. For footwear, opt for Oxford shoes.

Layered look

This outfit represents the “everything works” look. You can often times just layer multiple items to achieve a warm preppy winter outfit. A polo shirr above an Oxford shirt underneath a sweater? Why not? Just try to not make your silhouette go to waste completely and try not to sweat too much.

How to accessorise properly in winter

As we’ve seen many outfits that feature lots of layering and long sleeves, it can be a little difficult to accessorise properly. Therefore, you will want to opt for some core basics that will make a great appearance nevertheless:

  • Beanies
  • Scarfs
  • Gloves
  • Watches
  • Rings
  • Earcovers
  • Small necklaces

will make a great appearance on preppy winter outfits. Opt for simple accessories and try to match them to the outfit and you will get a perfect preppy appearance in this cold season.

Final thoughts on preppy winter outfit ideas

As you can see from this article, preppy winter outfits make a great appearance and offer you tons of ways to set yourself apart from those boring-looking winter outfits you see everyday. By keeping the 3 core elements in mind, you can go and create your own preppy winter outfits.


What are the best preppy brands for winter outfits?

The best preppy brands for winter include Ralph Lauren, J. Crew, and Vineyard Vines.

What are the best preppy shoes for winter?

Chelsea boots, knee-high boots, elegant sneakers, and Oxford shoes offer a great fit for winter.

Scroll to Top