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Early Winter Date Outfits

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Fall is coming to a foreseeable end, and yet, it’s not quite the reign of cold front terror that is February. This is prime time to wear the cutest things that winter has to offer before shit really hits the fan cold-wise. And what better time to prance around in cute winter items than on a date? It’s enough to make you forget all about those sundresses and rompers (ooh controversy!) of yester-season.

The Great Muppet Caper

Hear me out on the cape situation, OK? As long as you’re not trying to be Andre Leon Talley and try pairing it with something stable and sensible like jeans and flat boots, it can actually turn out pretty well. I’m a huge fan of these leggings-cut jeans from Levi’s, which are literally like $60. Almost no matter what you’re wearing, chocolate brown riding boots will go with it. It’s a perfect way to look polished and stay comfortable. Total movie at home date category.

Madeleine In The City

It’s like Madeleine was reborn in New York City, but about 100% less of a Cathy cartoon than Lea Thompson. Yes, this can veer off in the too-cutsey direction, but if you don’t go overboard with accessories and hair, you’re solid. This can be a great outfit for anything from a first coffee date to going on your first vacation together.

Madeleine In The City

Madeleine In The City by AGgimmesomesilver featuring black leggings

Cashmere Money Millionaires

Even though cashmere can be kind of pricey, there is a way to sift through all the sales of the nicer stores for cashmere gear to make it worth your while. One of the most exciting things about this winter is cashmere blend trenches and duffel coats (like the amazing J.Crew one in camel below). Why not go all the way with it and get into a cozy cashmere dress, throw on some leggings, and clogs and go to the movies with your date? BTW, clogs are amazing cold-weather shoes, plus the fact that they’ve super super hot for the past 2 seasons. Oh, and if you ask me, necklaces and accessories are the total better option if you’re going to give into the Anthropologie quirk-industrial complex.

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Anna G - Caliburg Contributor

Anna G - Caliburg Contributor

Anna G. is a Southern California native living in the Williamsburg area of Brooklyn since 2005. Anna is constantly trying to unite her love of CA sunshine and the excitement of the New York urban jungle, all the while trying to keep her unwieldy credit card debt under control, and look fabulous at brunch, no matter how un-showered and hungover.