How to Wear Drapey Drawstring Pants and Not Look Like You Are Wearing Pajamas

Drapey Drawstring PantsWhen I see drapey pants with a drawstring or elastic waistband I run in the opposite direction.  Harem pants?  No way, it ain’t Hammer Time over here, never will be.  Pants that make my ass look like I’m smuggling sausage links down my pants?  Uh-uh.  And an elastic waist?  Are you kidding me?  So imagine my surprise when I complimented a mom on her super adorable, comfy looking summery drapey drawstring pants, that were acid wash, no less?  Acid Wash?  Perhaps my 80’s New Jersey was trying to come forth or I was suffering from heat stroke.

Anyway, despite the fact that I’m not entirely sold on pants that look like pajama bottoms, and they could potentially make me look like a pear wrapped in a napkin, ever since seeing this woman I’ve seen this trend everywhere.  That said, if you’ve been considering a pair of drapey drawstring pants as a summer staple, in today’s One Item, Five Fashionable Ways, I am giving my tips on how to look stylish, and not like you rolled out of bed and couldn’t be bothered to change out of your jammies.  Seriously, I have a pair of Uniqlo pajama bottoms that look almost identical to this burgundy J. Crew pair I am featuring.

How to Wear Drapey Drawstring Pants

Outfit #1- To make a tank top and drapey pants not look like pajamas

For casual days, a pair of drawstring pants is definitely an easy way to go.  However, if you just throw on a tank top and a pair of flip flops nobody is going to think you bothered to get dressed.  For a super casual look like this, adding some finishing polish is important.  I’m not saying you have to get super gussied up, after all this is about ease, but there is a big difference between a slothy casual look and easy causal.

Take, for example how I styled this tank from Modcloth with these pants.  Instead of pair of shoes you’d wear to get a pedicure, or not get a fungal infection in the shower at the gym, I used a sparkly pair of comfortable sandals from Anthropologie, a simple chevron necklace, a colorful tote bag and denim jacket from Target.  Now you can go do casual things and not look like you just rolled out of bed, even if you did.

Outfit #2- To dress up

These may not be the pants you would wear to go to an ultra-dressy function but you might want to wear them on a warm evening with friends or for daytime plans that require more effort than putting a comb through your hair.  You can easily elevate these pants and even wear them with heels.  I don’t recommend a pair of spindly stilettos but a wedge or stack heel would work.  Heels like this could also be a great solution because they lengthen the body.  Drapey drawstring pants have the potential to add unnecessary bulk to the body and by countering it with length you can shave off the unintended look of fullness.

To add some dressiness, I styled these pants with a white top from Topshop, a pair of gold wedges from Steve Madden, a gold Coach wristlet and a Stella & Dot necklace.

Outfit #3- Don’t forget the waist

If the whole reason you like pants like these is because you can just put them on and let it all go, be warned, you are doing yourself a disservice.  Before you just throw on some loose tunic top with a drapey pair of pants, thinking that nobody will see your lumps and bumps, know that this is not true.  Unless you are built like a blade of grass, this will fail miserably.  However, there is a way to embrace ease without sacrificing your body to the Gods of Eternal Blobbiness.

As you can see in this outfit, I took a relaxed chambray shirt from French Connection and just added a belt.  What this does is creates a waist which allows you to look carefree but more structured.  To finish the look, without losing comfort, I styled this outfit with a pair of Anthropologie sandals, a tote bag from Ivanka Trump and fun earrings from Jessica Simpson.  Nothing about this outfit says fussy but it doesn’t say “I could care less about what I look like” either.

Outfit #4- Add a more novel top

Again, I am not saying you dress these pants to the hilt but by styling thesm beyond a basic t-shirt or tank can elevate them to an outfit that should be seen outdoors.  Here, for example, I added a sleeveless top from Anthropologie and, with the  addition of accessories consisting of a cobalt handbag, a coral pair of flats, a pair of earrings and a bracelet, the outfit looks more purposeful than something you might wear to catch up on your Saturday morning cartoons.

Also note, another way to make a casual outfit look more interesting is to play with color combining in unique and thoughtful ways.  It’s not as hard as you think.  In this outfit all I did was reference the colors found in the top and pulled accessories colors from there.

Outfit #5- Super easy without sacrificing style

If your thought about these pants is that you don’t want to add any effort because the whole point of them is to not put any effort forth, you can’t get much easier than throwing on a tank and sandals.  However, similar to the first look, the steps involved in this outfit take no more effort than if you styled these pants with more casual ones.  You have to wear a top if you are leaving the house (just a wild guess), need to wear shoes and will probably need to carry a bag of some sort.

What separates a bad outfit from a good outfit is sometimes the simplest of things.  In this outfit, instead of a basic tank I chose printed one from Boden that is probably just as comfortable as the crumpled one at the bottom of your pajama/yoga clothes drawer, a pair of yellow sandals that are equally comfortable to a more boring pair of sandals you own and a conversational tote that doesn’t cost a heck of a lot more than the free tote you got for donating to Public Television.  Plus, a pair of stud earrings.  How hard is that?  Yet, notice the difference.  This outfit looks thoughtful even though it really didn’t take much thought to put together.

The key to wearing drapey drawstring pants well is to wear them with more elevated pieces with them so that they get upgraded to something greater than looking like pajama bottoms, unless you want them to look that way, of course.

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  • KimM.

    “…it ain’t Hammer Time over here, never will be. Pants that make my ass look like I’m smuggling sausage links down my pants?” I just busted out laughing at this Bridgette! Although I’ll probably never embrace this particular trend, I do really like the way you’ve styled them.

    • Haha, thanks! Needless to say, I won’t be wearing them either, but it was fun to write about them! I guess we will both appreciate the looks I styled from a great distance!!

  • RohnaH

    I have a muffin top I like to camouflage, but I’m afraid the bow would sit right on top of it and be like a neon sign…any tips there? (other than don’t buy pants like this??)

    • Bows can be a lady with a tummy’s worst nightmare! You could just remove the drawstring and have elastic either put in or tightened if there isn’t any in there.

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  • Amy Johnson

    I love drapey pants and I usual wear them when traveling or for long car trips. I also usually wear them with heels or a fancy flat so they look more like dress pants and not pajama pants.

  • Tamara Hudes Agarwal

    I know long flowy tops are in right now, but I think drapey pants look great with a fitted scoop neck tee. Especially on someone with a relatively small waist.

    • I agree! Too much drape and you can look like a big tent!