Happy December! It’s been a whirlwind last few weeks with the Thanksgiving holiday and the launch of my online clothing boutique, Pretty Neutral. But I’m back this week with another edition of What to Wear Where. This week, we’re talking about the perfect outfit of the day on a winter weekend getaway. Whether you’re traveling to visit family or for a short vacation, this outfit will take you from day to night with a quick change of shoes.

For more outfit inspo, be sure to check out the other What to Wear Where posts HERE!

Outfit of the Day on a Winter Weekend Getaway

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I love versatilite outfits that can take you from day to night easily. It’s especially important to have these types of outfit options when you’re traveling. You might be out and about throughout the day sightseeing, shopping etc. and don’t want to have to come back and completely start over to go to dinner. No one wants to waste time getting ready twice in one day when you can use that time to explore.

Even if you’re not traveling, it’s still nice to have transitional outfits in your wardrobe and this all-black look is no exception. Plus you’ll be able to mix and match other pieces in your wardrobe with any of these black pieces to create multiple other outfits.

Black Faux Fur Coat

This is my all time FAVORITE coat for many reasons. First, you can dress this coat up or down, so you can get a good price per wear out of it. Secondly, it looks so chic with the black fur and accentuated collar. And finally it’s incredibly warm. Since the temps are going to continue to drop in Kentucky, I’m going to need warm outerwear from here on out until winter ends. It comes in a variety of other colors too! But I’m partial to the black because it goes with everything.

I ordered a small which is a size up from my normal size because they didn’t have an XS in stock. However, I’m glad it worked out that way because I really like the slightly oversized fit.

Outfit of the Day on a Winter Weekend Getaway

Monochromatic Black Outfit

A monochromatic outfit always looks so chic, whether it’s all black, blush, white etc. I started with this oversized sweater that’s legging friendly. It’s naturally an oversized fit, so I’d recommend getting your true size. I’m wearing an XS.

I paired the sweater with these faux leather leggings by Commando. They have an extra-high control waist for a supportive yet comfortable feel. I sized up one to a small.

Day-to-Night Shoes

To break up the monochromatic look of the black, I styled this look with knee-high snakeskin boots. They’re chic with a little bit of edge. This would be a perfect night out look on your weekend getaway. During the day, you can pair sneakers like these or these with the outfit. Then, when you’re ready to go to dinner, you can change into these boots for a dressier night-out look.

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Outfit of the Day on a Winter Weekend Getaway


For travel, I like to carry a larger handbag to keep all my necessities in. This MCM bag is one of my favorites, but the specific color is out of stock. I linked the same design HERE but in black. It’s great because it’s big enough to keep everything you need in it, yet not too big that it’s too heavy to carry around. It also can be carried as a crossbody.

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Do you like wearing monochromatic looks? If so, which color do you like wearing best? Let me know in the comments below!

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Outfit of the Day on a Winter Weekend Getaway
XO Amanda

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