7 Date Outfits That Are Both Stylish and Comfortable

Going on dates can definitely be uncomfortable—therefore, your outfit should never be. The fine line between cute and practical is, well, fine, but thanks to the seven fashion girls ahead, we think we've figured out just how to have our cake and eat it, too. 

Ahead, see the comfortable date outfits fashion bloggers have been inspiring us with lately. What we've learned from these ladies is that in order to achieve such a mind-boggling balance, you need to combine the pieces in your closet that make you feel special with the items that make you feel at home. Because as much as we'd like to wear sweatpants out on a first date, that might not be the best option (but, to each her own). In this case, it's all about compromise. 

Go on to shop the seven comfortable date outfits fashion girls are wearing this fall. 


Moto Jacket + White T-Shirt + Skinny Jeans + Bold Shoes
(Image credit: Nicolette Mason)

On Nicolette Mason: Levi's 711 Skinny Jean ($55) 

Shop the look:


Sweater + Printed Skirt + Red Heels
(Image credit: Always Judging )

On Courtney Trop: Iro Herina Knit Top ($120) and Douzten Skirt ($216); Céline shoes

Shop the look:


Statement Jacket + Camisole + Vintage Denim + Strappy Sandals
(Image credit: Wide Eyed Legless )

On Madelynn Furlong: Vintage jacket, top, and jeans


Oversize Denim Jacket + Long Slip Dress + Sneakers
(Image credit: Sincerely Jules )

On Julie Sarinana: Vintage denim jacket; Sincerely Jules Millie Slip Dress ($149); Golden Goose Leather Superstar Low Sneakers ($445)


Matching Silky Set + Suede Mules
(Image credit: Happily Grey)

On Mary Seng: Prada Slant Heel Mule ($620); J.W.Anderson Pierce Medium Leather Shoulder Bag ($1690) 


Silk Minidress + Kitten Heels + Architectural Bag
(Image credit: Lust for Life)

On Olivia Lopez: Protagonist dress; Manolo Blahnik heels; Carolina Santo Domingo Amphora Mini Top Handle Bag ($725)


Chunky Sweater + Leather Pants + Sparkly Heels
(Image credit: Collage Vintage)

On Sara Escudero: Chloé bag

Lauren Eggertsen
Editorial Director

Hi, it's Lauren here! I've been working in the fashion industry since my interning days back in college. I started my career at The Zoe Report and eventually landed at Who What Wear, where I have been for seven years now. Currently, I am Editorial Director, providing all of you with the latest and greatest in trends and shopping. My personal style is always changing, but right now, my closet is filled with tailored separates, contemporary bags, and lots of statement shoes. I moved to New York about three years ago but am originally from Orange County, California. I went to school at Pepperdine University and moved to Los Angeles immediately after graduation.