When it’s so cold outside, it’s a great time to create a capsule wardrobe of Preppy outfits for Winter, as warmth and longevity of your style are extra essential. Below is everything I am wearing all Winter long as a self-proclaimed prepster who loves style that never changes. It’s only my absolute favorites for the long term. (Who wants to buy new boots every few years?!)
Mix and match these pieces to create the most preppy outfits for Winter.
Preppy Outfits for Winter
Preppy Winter Coats
L.L. Bean Classic Lambswool Duffel Coat
L.L. Bean’s Classic Lambswool Duffel Coat reminds me of Home Alone. The length, color, fit and toggles feel so classic 90s prep, yet timeless. This jacket will be my next outerwear investment and I hope to have it for decades.
Patagonia Puffer Coat
A Patagonia puffer coat provides warmth in a classic style from a great, very socially responsible brand that stands the test of time. Their fits are feminine yet maintain that “forever” look.
Preppy Winter Shoes
Allbirds Tree Breezers
Allbirds tree breezers bring warmth to the preppy look of a ballet flat. Besides being comfortable, breathable, sustainable and washable, they are lined with merino wool and, to this day, remain the warmest shoes I own. They made my list of favorite things is 2019, and they are still my go to for the warmest of shoes. I simply know my feet won’t end up cold when I put them on.
I wear my regular size in Allbirds.
Birdies — The Heron in Velvet
Birdies are slippers that can also be worn as flats. And they really do work in both contexts! They have the comfort and flexibility of a slipper with the sturdiness of a flat. The linings have several layers that provide long lasting comfort whether you’re home or out. I have no problem wearing them out, and at home, I like to wear them when we have guests, so I’m comfortable but yet slightly more elevated than standard slippers. I have several pairs, but in Winter, my go to style is The Heron in cozy velvet.
I always size up ½ size in Birdies.
L.L. Bean Wicked Good Slippers
L.L. Bean Wicked Good Slippers have earned the title of “Best Slippers Ever Made.” A pair sells every 7 seconds during the peak of December — in great part due to their classic style and warmth. I love to wear them around the house both with pajamas and clothes so much they made my list of favorite things in 2020. I find them to be more slipper like and less “shoe” like than other competitors, but they do also have a rubber bottom if you need to run outside quickly. I have heard so many people say they have worn them over a decade!
L.L. Bean Wicked Good Slippers run true to size for me, but I would recommend that half sizes size down.
L.L. Bean Bean Boots
When I think of preppy Winter books, L.L. Bean’s Bean Boots immediately come to mind. They have a style that never changes and are known for keeping lots of feet dry and happy in the rain, snow and ice. They are the type of thing you buy once and wear forever!
I size down a full size in L.L. Bean Boots.
Hunter Adjustable Back Gloss Waterproof Rain Boots
Hunter Adjustable Back Gloss Waterproof Rain Boots are a much more modern preppy look for Winter, having gained mass appeal in the last decade. Their look is simple and streamlined, and they also make for a great “buy once and wear forever.” In Winter, I like to line mine with Welly fleece boot socks for added warmth.
I size down a full size in Hunter boots, even when I add the sock lining.
Preppy Hats / Scarves / Accessories
A Barbour scarf is the perfect way to accessorize preppy outfits for Winter with a preppy print, as they often come in very classic plaids. I love how affordable they are for a higher end brand, quality material and craftsmanship and a look that lasts!
L.L. Bean Cotton Ragg Socks
Your preppy outfits for Winter without be complete without the timeless L.L. Bean cotton ragg socks, which are essential for layering with boots. Be sure to let them peak out of the top.
Preppy Winter Sweaters / Tops
Dudley Stephens Fleece Tops
Dudley Stephens fleece tops have gained a lot of steam in the preppy style community, and for VERY good reason. Their clean lines and high necklines scream “preppy” and put together yet they also have the comfort and warmth of your favorite fleece — in a much more sustainable, higher end fabric. I have several and now consider them essential to my wardrobe. I love how they can be dressed up or down. They made my list of favorite things in 2020, and I don’t see my love slowing down any time soon.
I prefer the velo fleece option (versus terry) because it’s thicker and warmer, and I wear my usual size.
Barefoot Dreams Cardigans
Barefoot Dreams cardigans are sooo soft and cozy, and perhaps no piece of clothing is more preppy than a cardigan. For warmth and comfort in my preppy outfits for Winter, I wear them over everything — period.
Barefoot Dreams cardigans run true to size for me, but if you are between sizes, I would probably suggest that you size down.
J.Crew Supersoft Yarn Sweaters
J. Crew’s supersoft yarn sweaters are a new preppy fave for Winter. I purchased one after hearing a lot of people rave about them, and I haven’t stopped since then, especially when there’s a good sale! They often have high mock necks for that classic look of a turtleneck, but are more soft and cozy than a traditional wool sweater. In other words, they aren’t itchy!
I wear my regular size in J. Crew’s supersoft yarn sweaters, and I especially love the preppy stripe prints.
Spanx Velvet Leggings
Spanx velvet leggings are undoubtedly my favorite Winter pants, and you can wear them however you wish to maintain the look of Preppy outfits for Winter. I find them to be even more flattering than the cult favorite faux leather leggings, and the velvet material gives them a more classic Winter style.
I size up in Spanx velvet leggings.
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