How to wear pajama pants: 11 Style Panel tips for taking sleepwear trend out of bed and onto the streets

How to wear pajama pants
How to wear pajama pants

After Stella McCartney and Diane von Furstenberg showed loose fitting, printed pajama-style pants on their respective runways for Spring 2012, the trend cemented itself for seasons to come. Since, everyone from Tommy Hilfiger to Dries Van Noten have shown the look. on the streets, J Crew creative director Jenna Lyons and Rihanna have both made wearing the trend look effortless. But while pajama dressing sure is trendy, it may not surprise you to hear that its not as simple as leaving the house in the same outfit you slept in.

Style, fit and fabric are all things that we need to consider when deciding how to wear pajama pants. You want the look to be flattering and streamlined, which can often be the antithesis of the way pajama pants are made. Same goes for loose fitting pajama blouses.

This week we challenged our Style Panel to show off how to wear pajama pants and share their tips. Curvy Geekery’s Mo Handahu swore that she would never try this trend, but looks amazing in her matching blouse and pants that fit her perfectly. This trend is all about fit! Inherited Jeans’ Stephanie Koch went casual with her styling and added a leather jacket, smoking slippers and a lace t-shirt to her silk track pants.

Question 37: Pajama dressing is one of the hardest trends to adapt for everyday. What’s your advice on how to wear pajama pants? Read the answers now! »


How to wear pajama pants Krystin Lee

Krystin Lee, 26
Toronto | Suburban Faux-Pas

I have to admit, I was a bit timid to join the pajama trend party. I admired the blouses with matching pants but thought I couldn’t quite make that mine. However, when I stumbled across these pants (recent find from Forever 21), I couldn’t resist. They have the silk texture like pajamas and definitely the print, but the harem style shape made me feel way more comfortable sporting them in public. I opted for a more casual look with these pants by pairing them with a jean jacket and simple striped shirt.

Krystin’s wearing: Jacket, Old Navy. T-shirt and pants, Forever 21. Shoes, Zara. Bag, Prada. Necklaces, c/o My Name Necklace Canada, Tryst Jewellery. Sunglasses, Gucci.

How to wear pajama pants Mo Handahu

Mo Handahu, 29
Halifax | Curvy Geekery

The pajama look is one trend I never thought I’d try. The moment I read this week’s challenge I laughed as I recalled a vow I made to myself a few months back. While at a thrift store I found these matching pants and blouse reminiscent of pajamas which I vowed I’d never wear together … until now.  Being that I am always up for a challenge I was ok with not keeping my word.  In hindsight I might have just overreacted in the store as this pairing is actually not that bad. The top was a little too loose so I decided to make a knot, which was more flattering to me.  This remains one of my least favourite trends, but I’m glad I gave it a try! 

Mo’s wearing: Blouse, thrifted. Pants, thrifted. Earrings, De Nova at Second Storey. Shoes, The Bay. Necklace and bracelet, thrifted.

How to wear pajama pants Cara McLeay

Cara McLeay, 28
Vancouver | A Fashion Love Affair

Who doesn’t want to wear pajamas all day?! The trick to keeping the look day-time appropriate is to add a structured element, like a belt, or in my case, a blazer.

Cara’s wearing: Top, Shop Sosie. Blazer and pants, StyleMint. Heels, Zara. Bag, Marc by Marc Jacobs. Necklace, Banana Republic.

How to wear pajama pants Stephanie Koch

Stephanie Koch, 27
Kelowna | Inherited Jeans

I will admit this trend is quite tricky to style and probably isn’t for everyone. It might even be easier come warmer weather when you can sport silky pieces with less bulk. In the meantime, I went for an ensemble with pajama references but avoided being too literal. These silk track pants give me comfort without being sweats, and taper nicely at the bottom to keep my shape. When paired with a lace tee and printed smoking slippers you get a look that’s acceptable outside of your bedroom for casual weekend activities!

Stephanie’s wearing: Jacket, Joe Fresh. T-shirt, Talula by Aritzia. Pants, Club Monaco. Shoes, Zara. Sunglasses, Marc by Marc Jacobs. Cuff, Crown and Glitter. Tote, Ports 1961.

How to wear pajama pants Melanie Morais

Melanie Morais, 24
Edson, AB| BornLippy

It’s always interesting to see what becomes a trend in the world of fashion. I cannot be more surprised when dressing in pajama-like clothing became popular. To be perfectly honest, it is one of my biggest pet peeves when I see people wear pajamas in public but there is a way to make it look more acceptable. I took the more subtle approach by pairing pajama-like pants with a silky pocket top. The key to this trend is to stick to wearing silky material and not flannel, etc. There are plenty of beautiful silky looking pajama sets on the market right now that could be worn tucked into trousers or jeans you already own or pairing the pajama pants with your favourite blouse and heels! I definitely think the more subtle approach to this trend is what would work best for most body types. So pull out those silky tops and pants and make the trend your own!

Melanie’s wearing: Top, H&M. Pants, Forever 21. Scarf, Joe Fresh. Shoes, Jeffrey Campbell. Watch, Michael Kors. Bracelet, handmade.

How to wear pajama pants KD Faustino

KD Faustino, 28
Calgary | The Girl With the Messy Hair

Probably one of the hardest trends to pull off without looking like you’re about to hit the sack or just getting out of it: THE PAJAMA. It can make you look like a city girl whose effortlessly chic or a complete utter hobo. To make it look more urban than sloppy, choose a fabric that looks more luxurious like silk and if you’re going for prints, make sure that they are intricate and subtle. Some people would opt for a pajama set but if you don’t have that handy, making the look monochromatic would suffice. Add a more downtown vibe to it instead of it screaming “beach” (or “bed”) by wearing a wide-brimmed hat, gold/rose gold jewels and ankle boots.

KD’s wearing: Top, Joe Fresh. Pajama, Joe Fresh. Boots, Go Jane. Hat, Le Chateau. Necklace, My Name Necklace Canada. Watch, Michael Kors. Jewels, ILY Couture, Stack-em Jewelry, Hillberg and Berk.

How to wear pajama pants Jacquelyn Son

Jacquelyn Son, 20
Vancouver | Style Worthwhile

It’s ironic how much effort you have to put in just to pull together an ‘effortless chic’ look. It actually takes a lot of work to make your hair the perfect ‘messy’ or to perfectly tuck in your boyfriend tee into your jeans. The pajama style is no different. My tip: you want to look relaxed and laid-back, but not like you just rolled out of bed without showering. For me, I prefer the plain, solid colour pj-style top. But if you’re more daring, you can go for a bold printed pj shirt. I would recommended a looser fit, so you can move around more freely and it adds to the whole easygoing vibe. You can pair it with almost anything you like on the bottom, as long as it’s a bit more fitted than your top. Go for whatever you feel comfortable with – a skirt/leggings/pants/skinnies.

Jacquelyn’s wearing: Top and pants, Forever 21. Boots, Nine West.

How to wear pajama pants Kristin MacDonald

Kristin MacDonald, 27
Fredericton, NB | Doll Parade

I’ve got to admit, even the words “pajama dressing” are a little off putting for me, since, in my mind, pajamas belong in the bed and not in my office. That said, being inspired by a challenge like I usually am, I decided to tune into my adventurous side and pair my very silkiest blouse with some oversized trousers for something slightly “pajama esque”. This is the closest I can come, folks. I came to realize that there is something slightly understated & sexy about this simple pairing, and I’d hate to admit that I may be just a little bit converted. Next on my radar: a pair of flowing silk pants in a bright hue for the springtime.

How to wear pajama pants Barbara Ann Solomon

Barbara Ann Solomon, 25
Toronto | Barbara Ann’s Style Blog

Since the spring of 2012 I have been obsessed with staying in my pajamas all day long, and luckily it’s right on trend. This look is all about comfort and ease, with luxe fabrics draped loosely—it’s very bohemian and carefree. The print should be fun, right now I’ve been collecting floral shirts and pants to mix-and-match around the office during the spring. Wearing this trend around the office, I would recommend choosing more formal pieces, like blazers and dress pants, and of course a great pair of heels, to ensure no one thinks you just stumbled out of bed.

Barbara Ann’s wearing: Shirt, Vintage. Pants, Loft. Boots, Michael Kors. Necklace, Vintage. Purse, Marc by Marc Jacobs. 

How to wear pajama pants Christina Cravero

Christina Cravero, 27
Toronto | The Style Mogul

While living in Portugal I came across numerous girls sporting the ‘pajama pant’.  I never really got hooked on the pajama pant trend because I always thought it looked sloppy on my body shape, however, after trying on many different styles I learned that you must look at a pant that’s more fitted with an elastic bottom, and it must be paired with a fitted shirt, cropped jacket/blazer, low-high heels and of course fabulous accessories!

Christina’s wearing: Pants, Fitzroy Boutique. Top and jacket, H&M. Wedges, Chanel. Bag, Danier. Pins and Necklace, Vintage. Sunglasses, House of Harlow.

How to wear pajama pants Kayla Short

Kayla Short, 26
Halifax | Short Presents

Who doesn’t love silk pjs? Loose billowy fabrics, soft satin against your skin? What’s not to love about this trend? I don’t know about you, but the first thing I go for after a long hard day at work is my cozies.

With pajama dressing you don’t want to look like you just rolled out of bed, and slept walked yourself into the office, but rather you’ve incorporated some of your pj pieces into the mix into a sort of sophisticated care-free way.

Make sure your pajama pieces look purposeful; this is a classic, gentleman’s look, so stick with trousers, shirts, or shorts in high quality fabrics like glossy, slippery silk, or satin. When incorporating pajama pieces I like to wear elegant accessories like a great bag, or a stacked arm party. Always opt for a sophisticated shoe like a great pump and/or something with height.

Kayla is wearing: Coat, BB Dakota. Waffle Shirt, Gap. Pink Blouse,  American Apparel. Silk Trousers, H&M. Boots, Vince Camuto. Scarf, Banana Republic. Gloves: Ralph Lauren. Bag, Christopher Kon.

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