a prep in my step | how to dress preppy in the winter

it will comes as no surprise that preppy is my go-to style. it always as been, and it always will be.  preppy lends itself naturally to the spring and summer months.  but how do we keep that aesthetic alive and fresh when we’re in the cold, dreary depths of winter?  if you’re looking for some essential items to prep up your wardrobe—or if you’re looking for a little color to offset the gray days—today’s post is for you.  i’m going to give you some outfit essentials that will show you exactly how to keep the torch burning strong—how to dress preppy in the winter. 

how to dress preppy in the winter

yesterday on the blog, i was feeling neutral:  it was all about the whites, grays, and blacks.  (and for those of you that are wondering, Ann Taylor restocked the herringbone shawl collar wrap coat that’s all the rage.  so if you were looking to pick one up and missed out, make sure to head over and grab one.) 

today, it’s all about the color pop.  we’re no strangers to color over here on the blog, and we talked extensively last fall on how to introduce color into your wardrobe. preppy is all about well-placed color additions, and the outfit of the day features a blue monochromatic base.  some people shy away from monochrome, as it can sometimes feel redundant and/or aesthetically uninteresting.  however, monochrome is an easy way to introduce color to your wardrobe, and a simple way to successfully do it is by picking a base—shirt/pant, sweater/shirt—combination that runs the two ends of a particular shade spectrum.

here, i’ve chosen a dark blue gingham shirt and layered it with a light blue sweater from J.Crew. i’ve added visual interest to the outfit by pairing my base with a pair of houndstooth jeans that pick up both colors.  

similar puffer jacket | gingham shirt | sweater | houndstooth jeans | similar hobo bag | loafers | similar scarf | sunglasses 

too cold for loafers?  

i’m fortunate that Athens weather often permits me loafers during the winter. if you too live in an equally forgiving climate, a pair of penny loafers is an obvious but timeless way of prepping up an outfit.  i picked this pair up from J.Crew, but if you’re looking for alternatives, check out these Oxford loafers i featured last week on the blog.  but if it’s Minneapolis-like weather where you are, make sure to check out this Easy Spirit winter shoe guide I put together a few weeks ago.  there are a couple of booties that would go perfectly with today’s outfit! 

similar puffer jacket | gingham shirt | sweater | houndstooth jeans | similar hobo bag | loafers | similar scarf | sunglasses 

a puffer jacket is an essential

a puffer jacket is one of my top 5 essential winter jackets to own.  not only is it quintessentially preppy, but it’s just so darn versatile.  if you’re headed to work, out and about shopping, or meeting a friend, reach for your puffer.  it’ll keep you warm, and you’ll look good while it’s doing it.   this one is older but i’ve found a similar one at Nordstrom—totally reasonably priced—but head to your favorite retailer for yours.  

similar puffer jacket | gingham shirt | sweater | houndstooth jeans | similar hobo bag | loafers | similar scarf | sunglasses 


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  1. Madeleine wrote:

    I’m a Mpls gal…cold, grey and snowy here. What is the current “hot” color to warm me up and make me “pop” while waiting for Spring….

    Posted 1.7.20
  2. Good morning Beth. You look great in these colors. So flattering with your hair color and complexion. I, too, love the classic preppy look. I really like the houndstooth jeans and gingham shirt. Is the shirt a very slim fit?
    We are fortunate to live in a milder winter climate.
    Although sometimes I wish for colder weather to wear heavier wool coats I love.
    I hope your new year is going well .
    Looking forward to 2020 fashion inspirations.

    Posted 1.7.20
  3. judy wrote:

    We don’t see you in much blue. Looks very youthful and fresh on you. Happy new year!

    Posted 1.7.20
  4. Julie Mycock wrote:

    Hi Beth, love the outfit and the colours really suit you xoxo

    Posted 1.7.20
  5. CHERYL BACA wrote:

    The link to the scarf pulls up a different scarf. Is the one you’re wearing available?

    Posted 1.7.20
    • hi cheryl,

      yes, the link in the blog post goes to a similar scarf. the scarf i’m wearing is more than five years old from J.Crew. the post has been updated. thanks so much for pointing this out.

      Posted 1.8.20
  6. Jana wrote:

    Love the blues. Is the jacket you’re wearing blue or black?

    Posted 1.7.20
  7. Lyn wrote:

    I have several puffer or quilted jackets, and vests, and I just love them. They are so light, not bulky feeling at all, and they are so warm. I have several at a higher price point – from Talbots. I have them in red, Saffron yellow, powder blue, white, mauve and navy. One is a Tommy Hilfiger and it is about 15 years old and still looks beautiful. I wanted to add another one, and I bought one in pink from Amazon Basics. I think it was only $39! Another thing I have done is buy several silky scarfs from Amazon in colors that go with the jackets. They keep the collars make-up free. One of the scarfs only cost about $5.00!! They add a hint of color and are warm around the neck. My favorite look is my saffron yellow jacket, black turtleneck and a multi-color scarf. Really cute.

    Posted 1.8.20
  8. Suzanne Smith wrote:

    The stripes are great here, coupled with the pants. I love puffer jackets–I don’t like them to be too bulky, but “just right.” What brand is the one you’re wearing? I like its simplicity. My problem is I have several in different colors and I always see another one I like! I guess I’m a sucker.

    Posted 1.8.20
  9. MCarme wrote:

    Hola Beth me pareces genial soy una gran admiradora tuya me lo paso fenomenal…felicidades

    Posted 1.14.20

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