Winter Lookbook 2019

It's that time of year again, and the familiar dilemma of whether to dress warm or chic can be unnecessarily stressful. But why choose one or the other, when you could have both? Dressing for the New England cold can be hard to do without looking like the Michelin man, but hopefully the following five outfits can give you inspiration when creating outfits of your own.



For this outfit, pair any close fitting top with an A-line skirt of your choice, and layer tights of varying thickness for an outfit that is both cute and cozy. A pair of tall boots like these ones, or some cute winter boots work well. If you want to feel extra warm, try layering a short cardigan under the final outer layer.




This outfit is by far the comfiest, and the most casual of all those pictured. Wide leg pants are especially useful in the winter, as you can wear the bulkiest inner layer; fleece tights or maybe even a pair of sweatpants if it’s one of those days, but either way, these pants will hide all your secrets. The fluffy sweater on top adds extra coziness, and also completely conceals the other long sleeved top I had on under this for extra warmth.




I find that winter outfits have the tendency to favor darker colors, so sticking with a lighter color scheme can shake things up a bit. Here, I layered a white turtleneck under a white vest, under a white puffer jacket for maximum comfort. If you’re anything like me, 80% of your jeans will have rips in them, so layering a pair of fleecy tights underneath can help you lengthen the time span between laundry loads a great deal. I love this outfit for it’s close resemblance to something my surprisingly stylish 5th grade ski instructor would wear.




For when you want something a little fancier, try layering a dress over a sweater and yet another pair of fleecy tights. Here, I matched the green from the dress to the green overcoat, which falls at about the same length of the dress itself, creating a very cohesive outfit. While for this outfit I went for my favorite high heeled midi boots, snow boots or tall boots would look just as good.




Arguably the preppiest outfit on the list, this is my go to for an easy and warm look that still keeps me safe from the blustery Connecticut winds. Wear any collared shirt under a sweater, and pair with riding boots and a black peacoat to look your most academic. While leaving the sweater untucked looks just as nice, I prefer to tuck my sweaters into the pants to clearly define my waistline, and avoid looking like a complete marshmallow.


This winter no matter what you choose to wear, make sure it’s something you feel confident and comfortable in, because it is way too cold out to buy into anybody else’s idea of what you should or shouldn’t wear. And of course, make sure to stay warm!