My New Obsession: Obscenely Comfortable Stylish Clothes

I call it fancy pajama dressing.  Clothes that look stylish and polished, but are so comfortable you could wear them to bed.  Everyone will tell you how fancy and gorgeous you look, and you’ll be able to go all night feeling as amazing as you look!  Stop stuffing yourself into dresses that feel like sausage casing, do yourself a favor and pick up one of these gorgeous ensembles for your next occasion!

Please click on any of the below images to be taken to the product purchase page online.  I may earn a small commission on purchases made.

Diane Von Furstenberg “Stephanie” Wrap Dress-$798 at Nordstrom

I love DVF’s wrap dresses, and I am currently obsessed with their maxi wraps.  It’s basically like wearing a bathrobe, but socially acceptable!  This fluttery silk dress will be perfect for any summer occasion.

Twisted Sleeve Skinny Dress- $195 at James Perse 

I cannot recommend James Perse knitwear enough.  It is so soft and crazy durable.  I have some of his pieces that are over a decade old and they still look new.  I love how you can take his dresses and dress them up with heels and a clutch for date night, or pair them with flip flops and a ponytail to run errands.  Either way, you look stylish and feel comfortable!

Ella Moss Tropical Silk Maxi Dress- $298 at Bloomingdale’s

Another perfect silk maxi dress.  I love the tropical print on this pullover style dress, it’s perfect for garden parties or evenings outdoors.

Midnight Jersey Maxi Dress- $168 at Splendid

I love Splendid dresses, their knitwear is this supremely comfortable blend of cotton and modal fiber that breathes, resists pilling, and holds dye better than regular cotton.  Their whole line of sundresses are perfect for running around town, or as beach cover-ups.  Dress this one up with some gold jewelry and a statement sandal and you could wear it out at night as well!

Calypso St. Barth “Caparica” Dress- $279 at Neiman Marcus Last Call

I am absolutely obsessed with the brand Calypso St. Barth.  Their silk dresses are comfortable and stylish, and so well made.  If you buy it before July 6th, this silk maxi dress is an additional 40% off, making it only $167.40!

Pair it With

Sophia Webster Seraphina Sandals- $395 at Nordstrom

Keep it dressy but comfy in these Sophia Webster sandals.  The bronze wing-shaped cutouts add a bit of glamour and go with everything!

Saint Laurent “Tribute” Sandal- $925 at Nordstrom


Hands-down the most comfortable heels I own, I can actually go all night in these and not have a single blister the next day, even when dancing!  Available in a variety of colors and two heel-heights, you’re sure to find a pair to match whatever dress you choose.

Arianna Flats- $795 at Giuseppe Zanotti

I love the idea of a jeweled sandal to add a little sophistication to a casual outfit.  Sometimes you just don’t want to be standing around in heels all night, but you still want to dress up.

To purchase any of these pieces, simply click on the picture to be taken to the product purchase page online.  I may earn a small commission on purchases made.

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