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The Dream: Wearing Your Pajamas in Public While Still Looking Good

My ideal outfit is one that I can sleep in. Some people like to rock athleisure wear so that at any given moment, they can hit the gym or at least look like they might.

I prefer an outfit that seamlessly transitions to taking a nap, aka my pajamas.

As a teenager, I wore my pajamas to school so often that after I graduated, they were banned from my high school. Sorry future minds slobs.

I just love to be comfortable. I recently wore a pair of high-wasted jeans on an airplane and within a half hour, I had turned into my 2-year-old when I tell him he can’t stick his hand down the garbage disposal. Lots of directionless fury and angst.

This is my baseline. I don’t even like wearing jeans or yoga pants because they feel too tight. And when the weather gets cold, my compulsion to only wear sweatpants hits the roof. Last winter I found myself yanking jeans over my sweatpants because I didn’t want to take them off, but I needed to be out in public.

I ran into my husband that day, and he took one look at me and said, “Are you wearing your pajamas under your clothes?”

By then I was sweating and so uncomfortable … sweatpants don’t exactly fit under jeans. I had gone too far. I was out of control.

So this year, I knew I needed a plan.

Am I going to do away with wearing my pajamas in public and act like an adult?

ABSOLUTELY NOT. DON’T BE RIDICULOUS.

With the help of my more stylish friend Martine, we have created a guide as to how I can continue to wear all my favorite lounge wear but still look like a functioning member of society.

Every outfit, except one, involves an elastic waistband. You heard me.

Jerry Seinfeld once said, “You know the message you’re sending out to the world with these sweatpants? You’re telling the world, ‘I give up. I can’t compete in normal society. I’m miserable, so I might as well be comfortable.’”

 I’m here to prove him wrong.

People, if I can do this, you can do this. Let’s go.

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Outfit No. 1:

Henley and black joggers or any soft black pair of pants.

2 Minutes:

Tuck that henley into your pants to lengthen your legs. Add heels to make yourself look fancy (but a non sneaker flat would totally work). Add a necklace and bracelet, purse and sunglasses. Done! You can go drop your kids at school with your chin way up in the air.

5 Minutes:

Add a jacket and lipstick. A cropped jacket is preferable since the rest of the outfit is loose. You are now ready to attend a wedding. OK maybe not, but you can go to work in this.

NOTE: None of these outfits need heels. Heels look great, but so will flats. Personally, when I walk in heels, I look and feel like a drunk toddler, so for most of these outfits, I’d need to wear flats or a very small heel.

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Outfit No. 2:

Your favorite black leggings and an oversized tunic/sweater.

2 minutes:

This look is the easiest one. Simply pair it with black boots (with or without a heel), sunglasses and a purse. Boom!

5 minutes:

Add a scarf and that hat you’re always too self-conscious to wear.

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Outfit No. 3:

T-shirt and joggers aka what I wear every second I am in my house.

2 minutes:

Put your hair up. A top knot or ponytail can fix many things. Put on your cutest cropped jacket. It doesn’t have to be leather, it can be jean or pleather, but it should be cropped to add a semblance of structure to the look. Add your trusted white sneakers and a good bag. White sneakers always clean up a look and the bag looks like you didn’t accidentally get locked out of your house!

5 minutes:

Add red lipstick because it’s fun! Add a scarf and some accessories — earrings, bracelets and a necklace always finish a look.

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Outfit No. 4:

Your trusted black leggings and a long-sleeve black shirt or sweater.

2 minutes:

A poncho can save your life or at least your outfit. Add a tall boot, and a purse and you’re ready to go.

5 minutes:

We really liked this look just how it was, but if you have the time, earrings and a necklace won’t hurt.

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Outfit No. 5:

White shirt (short sleeve or long sleeve) and soft pants. Pro tip: If you can find sweats that have a non-pajama-ish pattern, you are gold! These are houndstooth, and I bought them primarily because I felt like I could wear them both to bed and in public. Priorities people!

2 minutes:

Slip on some loafers or ballets flats and add a pop of unexpected color with your accessories. In this case, it’s the purse, but it could be a scarf or bandana, necklace, you name it! With the pajama pants, make sure you can see your shoes because that’s what will clean up the look. Again, a cropped jacket will elevate this outfit.

5 minutes:

Swap your flats for heels, add a scarf, jewelry, sunglasses, red lipstick and attitude.

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Outfit No. 6:

OK, so who actually sleeps in your spouse’s oversized dress shirt? Not me, but if you are having one of those movie star mornings where you actually are … and then reality hits, and you need to take your kids’ to the dentist, we have you covered.

2 minutes:

Tuck that shirt in your skinny jeans. You need a skinny jean to balance the oversized shirt. Add a clutch and heels. Leopard heels are all the rage right now, so if you have some old ones deep in your closet, it’s time to bring them out. A touch of leopard means you know fashion. Add some oversized glasses to camouflage your leftover mascara.

5 minutes:

Add a trench coat or any longer coat. Cape it because you’re so fancy. Add that beret you’re always too shy to wear because girl, you look good today.

Beauty does not have to be pain. Beauty can be pajamas.

You just need to know how to work it!


Written with the help of guest blogger Martine Leveillee.

Martine is a mama of three, fitness seeker, military wife, and learner of new languages who is currently living abroad.

She also loves styling and organizing closets. You can follow her here or here and read some of her other posts here and here.

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