8 Quintessentially Preppy Shoe Styles & How to Wear Them

In this style guide, I’m going to be sharing with you eight quintessentially preppy shoes to complete your outfits. Because if we’re going to be preppy, we may as well be preppy from head to toe. Let’s begin our preppy shoe guide!


New England boat shoes

1. Boat shoes

The first preppy shoes on the list are boat shoes. Boat shoes are definitely a part of that New England prep start uniform.

New England preppy style

When I think New England preppy, I’m thinking yachting, boating, and a nautical vibe. So the boat shoes fit in with that whole aesthetic.

The history of boat shoes

The shoes were created in the 1930s in Connecticut, and as the name suggests, they are a boating shoe, so they’re very practical with a rubber sole.

Feminine boat shoes

Boat shoes are a very classic and casual shoe for men, and they’re a great style of shoe for women as well. You can get them in lots of different feminine colors and patterns. They also have a more feminine version of the boat shoe for women, which is less chunky and more of a loafer style.

How to style boat shoes

Boat shoes are a great comfortable and practical summer shoe. When styling these shoes, I like to go for that coastal theme, so here I’ve paired them with a fitted white t-shirt and some seersucker shorts.

Classic pair of loafers

2. Loafers

The next pair of preppy shoes to own is a classic pair of loafers. They actually started as a hybrid shoe between casual and business styles.


You can get loafers that are more on the casual side; these lush velvet ones are more like a house slipper.

Dressed-up leather loafers

You can also get more dressed-up leather ones.

Preppy penny loafers

Like boat shoes, they’re great for men and women. A great preppy loafer style is the penny loafers which give a real academic vibe.

Penny loafers with socks

Back in the day, penny loafers were worn pretty much exclusively with socks, but as our fashion tastes have changed, most people wear them without socks. Go ahead and wear them with socks, though, if you want to create that cute retro feel.

How to style loafers

My loafers are suede, in a navy color, and they always give my outfits a dressed-up feel. These shoes slide onto my feet perfectly like Cinderella and are incredibly comfortable to wear. There are so many outfit options for loafers, but I think they look especially cute with a dress.

White leather Oxfords

3. Oxfords

Next up, continuing with that academic vibe, we have the Oxford shoes, also known as brogues. Oxford shoes are flat, lace-up shoes usually made out of leather.

Taylor Swift wearing Oxford shoes

Taylor Swift loves an Oxford shoe!

Duck boots

4. Duck boots

Next up, another more outdoor shoe - duck boots. These are a type of water-resistant boot, and they were first invented in 1911 in Maine by L. L. Bean.

The history of duck boots

They were originally created to keep one’s feet warm and dry when out hunting.

L.L. Bean duck boots

L.L. Bean is still a brand today, and they still make their iconic duck boots that are all handstitched in Maine.


I don’t know how I feel about duck boots. I don’t know if I would personally wear them, but at the same time, I would never say never.

How to wear hunter boots

5. Hunter boots

Speaking of waterproof preppy footwear, next up we have hunter boots. Hunter boots are designed for rain, and they’re also super cute - they come in lots of different fun colors. There are so many different ways to style Hunter boots, I think they look great with a pair of jeans but also with skirts and shorts.


My pair of boots are in a beautiful autumn red color, and I think they add a really nice pop of color to an outfit. I like to pair them with this American flag sweater because they tie in with the red of the design.

Classic Tory Burch ballet flats

6. Ballet flats

Ballet flats tend to come in and out of mainstream fashion. Fairly often, it seems like everybody's either loving them or hating them. I personally think that ballet flats always look classic and are a faithful shoe that won't let you down. 


As we know, preppy fashion is fairly trendless. There are a few little trends that go on, but the whole point of preppy style is that it’s very classic and clean-cut. I feel that ballet flats always add a feminine feel to an outfit, but I think that sometimes they can look a little bit twee, and you have to be careful what you pair them with. 

Zooey Deschanel wearing ballet flats

I wouldn’t put on a cute little skater dress with the flats because then you’re going to look like Zooey Deschanel very quickly. If that’s the look you’re going for, that’s fine, but personally, I like to stay away from twee and go more classic.

Jack Rogers shoes

7. Jack Rogers

These shoes are an absolute staple for me in the summertime. Jackie Kennedy is actually responsible for the creation of the Jack Rogers sandals. She was on holiday in Capri, Italy, and saw a pair of flat leather whip-stitch sandals, and she loved them so much that she brought them back to Palm Beach and had her local shoemaker make her up a few pairs. From there, Jack Rogers were born.

How to wear Jack Rogers shoes

I personally think that the classic white ones are always a great pair to own, but you can get them in many other colors as well. These shoes have the ease of a flip-flop, yet they have a very sophisticated feel.

Preppy white sneakers outfit

8. White sneakers

Another go-to shoe for me in the warmer months is a pair of classic white sneakers. There is a whole sneaker world out there, but a nice streamlined pair made out of canvas or leather is great for preppy looks. I love wearing white in summer because it is nice, bright, and good for hot weather. 


Preppy shoe guide

That brings our preppy shoe guide to a close. Let me know in the comments which preppy shoes are your favorite. If you enjoyed this and would like to read more about preppy fashion, check out these preppy style staples for women.

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