Four Crazy Comfortable Dressy Casual Outfits

4 Crazy Comfy Dressy Casual Outfits

Huge thanks to Nordstrom and ShopStyle for sponsoring this post

I used to think that dressing up automatically meant being uncomfortable.  Boy, was I wrong!  Over the years, I’ve discovered that you can look cute and put together while being completely comfortable.  Like, SO comfortable that you feel like you’re wearing pajamas.  Tell me, WHO DOESN’T WANT THAT?

Whenever I hear women say they don’t want to get dressed because they’d “rather be comfortable,” I want to take them by the hand and say, “Oh, friend.  Let me introduce you to a wonderful world of comfy goodness that will blow your mind!”  I’m a FIRM believer that you can have cute AND comfortable outfits, and I want to make sure you know that too!

Today I’m partnering with Nordstrom to share four dressy casual outfits full of pieces from their House Brands that are soooo soft, stretchy, and comfy that you’ll feel like you’re wearing pajamas.  Wear these for birthday celebrations, dates, parties, church, or any day you just want to feel put together AND super comfy!

SIZING: I’m 5’6″ and usually S/M or 6 in clothes, 8.5 to 9 in shoes.


blue maxi dress + denim jacket + cognac tote + sandals + pendant necklacedenim jacket + brown tote + blue maxi dress + pendant necklacesandals + denim jacket + blue maxi dress + cognac toteblue maxi dress + pendant necklace + brown tote + denim jacket

Maxi Dress – wearing size S
I recently shared this dress from All In Favor, but given that it’s been one of my favorite dresses for years, I just need to make sure you know about it. ? This dress is super effortless to wear.  I own this in solid black, this cobalt blue, a blue print that is no longer available, and just added a black floral print version!  I mean it, it’s one of my favorites!  (Find the solid black and cobalt blue ones HERE.  Find printed versions HERE.)

This is my go-to item for when I want an elevated casual outfit but have a pretty busy day and need to move around a lot, especially during warmer months when jeans are too warm.  A dress offers more air flow!  When I need to move around a lot, like bending down for kids or setting up equipment at events, the maxi length makes it easier to not flash people, which I’m pretty sure we can all appreciate. ?

A few notes: First, the bra situation.  These spaghetti straps require a strapless bra, which might make you wonder how on earth this could be comfortable if it requires a strapless bra.  I would have thought the same thing years ago before I finally found a strapless bra that stays in place all day.  I wear THIS strapless bra by Natori, and I was shocked that I never had to pull it up through hours of dancing!  Another one that is even more popular is THIS by Wacoal.  My size wasn’t in stock when I was last searching for a strapless bra, otherwise I would have tried that one.

Second note: Dresses in this type of material tend to cling a little on people’s rears, which is not ideal.  A simple remedy for that is wearing a slip underneath.  A slip prevents the dress from clinging.  Plus it smooths everything out back there, and that extra layer often aids in preventing underwear lines from showing. ??

Lastly, since this does not come in a petite length, several people mentioned taking advantage of Nordstrom’s free alterations!

This is one of my go-to pieces for to be a little dressed up but still casual, cute, and COMFY!  Find the solid colored ones HERE and printed ones HERE.

Shop The Outfit:
Dress: Nordstrom (exact-wearing size S; exact in more prints)
Jacket: Nordstrom (exact-wearing size M)
Sandals: Nordstrom (exact-size 9)
Tote: Nordstrom (exact)


striped maxi dress + denim jacket + grey purse + sandals + statement necklace denim jacket + striped maxi dress denim jacket + sandals + striped maxi dress statement necklace + striped maxi dress sandals + striped maxi dress + statement necklace

Smocked Bodice Dress – wearing size XS
Remember that orangey-red dress from BP. that I showed last week?  And how I told you there was a striped version that jumped into my cart?  Here it is!  Talk about CUTE! ?

I love the texture that the stretchy smocked bodice provides.  It’s also got crossed straps in the back!  It’s midi length, which I usually stay away from, but on me at 5’6” this one hits a bit lower than other midis.  Turns out I really like it!  It is a medium thickness and, of course, super soft and stretchy!

Last week when I showed the orange-red version, I wore it in size S.  I thought it fit pretty well, but Katie urged me to try XS, which is what I’m wearing here.  I think both sizes work, but XS looks great with a tighter fit at the bodice.  I have a small chest, so I think if my chest were larger I’d stick with S.  If unsure, order two sizes.  Nordstrom offers free return shipping on all orders, so it never hurts to order a couple sizes to get the right fit. ?

You can make this dress more casual with flats and a denim jacket, or you can dress it up with wedges or open toe heels.  Either way, you’ll feel like you’re wearing pajamas! ?

This dress is available in regular and plus sizes!  Find it HERE.  And again, if you’re petite, look into Nordstrom’s alterations services.

Shop The Outfit:
Dress: Nordstrom (exact-wearing size XS)
Jacket: Nordstrom (exact-wearing size M)
Sandals: (similar)
Bag: Nordstrom (similar)


blue jumpsuit + nude heels + pendant necklace + cognac clutch nude heels + blue jumpsuit + pendant necklace + cognac clutch pendant necklace + blue jumpsuit + cognac clutch cognac clutch + blue jumpsuit + statement necklace + nude heels

Jumpsuit – size M
Next up is a comfy jumpsuit!  Jumpsuits are great alternatives for dresses.  You get the comfort of pants (i.e. not having to worry about flashing anyone ???), but the waistbands on jumpsuits tend to be looser and more comfortable than waistbands on jeans or pants.  That means there’s less squeezing your midsection! ?

I first saw this jumpsuit while trying to help my sister-in-law find something to wear to a wedding that would allow her to chase an active 2 1/2 year old and breastfeed a 7-month old.  I finally decided to try it myself.  This jumpsuit is so, so comfy.  It’s made of that similar “pajama-like” material the maxi dresses are made of.  It’s on the thinner side, but therefore more breathable.  In addition to being soft and stretchy, it has drop shoulders, a cross-front neckline (making it breastfeeding-friendly), pockets, and jogger style legs.  Many jumpsuits have wider legs, but I LOVE this silhouette with fitted ankles!

This is a bit pricey, but given that you could wear this to a wedding, the price seems more reasonable, like the cost of a dress for a wedding.  This might even be more worth it since you can dress it down and wear it in more settings!  I dressed it up here with open toe heels and turquoise and gold jewelry, but you can dress it down for everyday wear with flat sandals and simpler jewelry.

This jumpsuit comes in navy and black in regular and petite sizes, and it comes in plus sizes in black! I’m wearing size M.  Size S fit me really well, but it hugged my rear just a tad more than I wanted it to given that the material is a bit thin, so I sized up to M.  For length, I’m 5’6” and the regular length hits me just right.  However, it didn’t work so well for my assistant Heather, who is 5’10”.  If you are around my height or maybe just a couple inches taller, or if you’re petite, this might be a great option for you to try!  See it in regular and petite HERE and plus sizes HERE.

Shop The Outfit:
Jumpsuit: Nordstrom (exact-wearing size M)
Jacket: Nordstrom (exact-wearing size M)
Shoes: (similar)
Clutch: (similar)


grey ruched dress+ white sneakers + denim jacket + pendant necklace + cognac totedenim jacket + grey ruched dress + pendant necklace + cognac tote pendant necklace + grey ruched dress grey ruched dress + denim jacket + pendant necklace + cognac tote cognac tote + grey ruched dress + denim jacket

Ruched Body-Con Dress – size M
For years I saw people rave about how comfortable and flattering this dress from Leith is for women of a variety of sizes.  I finally tried it, and I’ve gotta say, the rumors are true!  I have larger hips proportionate to my upper half, so I’m often skeptical of body-con dresses.  But, I found this dress to be really dang flattering!  The ruching all along the front is magical!  Plus, it’s totally stretchy and comfy, and the tulip hem makes it extra cute.

Even though this post is supposed to be about dressy casual outfits, I’m showing a dressed down look here with white sneakers and a denim jacket.  A body-con dress like this is very easy to dress up with open to sandals and a metallic statement necklace, so I wanted to show you how to make this more casual instead.

One note is that the front of this dress has two layers, which I love.  Not only is the ruching super flattering, but the extra layer helps me feel more secure in this form-fitting garment.  The back, however, is a single layer and is not as great at smoothing out bumps.  I would give this dress a billion stars if the back came with a double layer.  The good news is I’m able to wear a short slip underneath to give myself an extra layer.  That’ll do!

This dress comes in 11 colors, and it’d be fantastic for a dinner party, cruise, or special evening out.  With how flattering this dress is, you’d look ?!  I’m waiting for the teal one to come back in my size.  😀  See all the colors HERE.  Also, check out this dress in plus sizes HERE.

Shop The Outfit:
Dress: Nordstrom (exact-wearing size M)
Jacket: Nordstrom (exact-wearing size M)
Shoes: (similar)
Tote: Nordstrom (exact)


I am SO adamant that you can get dressed up and still be crazy comfy!  You don’t have to sacrifice comfort for style, so if you want both, check out some of these pieces!




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