The Best J.Crew Dresses for Fall

I’ve been a J.Crew fan for a very long time. There were a few seasons, and maybe even a few years, where I got bored of their styles. I didn’t order much, but in general, I’ve always really liked J.Crew. It was one of the main places I shopped when I was working in financial services. It was when had to dress for a corporate office environment. When they hired Olympia Gayot as the new creative director of womenswear and Crew Cuts, I began to love it even more. They have great office-appropriate dresses and pretty dresses for events and everyday wear, so I included a mix of styles.

While the ever-classic stripes and workwear styles will always be the bread and butter of J.Crew, I’ve been so excited about the new designs coming out over the last year or so. When I went through my closet a few weeks ago to clean things out for fall, I recognized a lack of fall dresses in my wardrobe. And since I’m pregnant and have a ways to go before we welcome baby #2, I wanted to buy a few dresses that would work well throughout the fall for an ever-growing bump.

I spent a few hours on their website and was truly blown away by so many of the styles they are carrying right now. I’ve always been a sucker for a polished collared shirt dress, and I really do think they do it best. I’m including dresses that won’t work for me while pregnant in this roundup since I know they may work for most of you.

Okay, let’s hop to it.

The Best J.Crew Dresses for Fall

Button Front Chino Dress

I looked for a chino dress like this all summer after finding a Zara romper that I was obsessed with. I really wanted a similar looking dress since rompers aren’t working as well for me now that I have a baby bump. Also, I love the olive green color (especially for fall), and the elastic waistband works as my bump continues to grow! (At least for a while!) I ordered a size 4, which is one size up from my regular size. If I wasn’t pregnant, I would have gotten a 2, so I’d say this runs true to size.

This dress would be a great option for a casual office, classroom setting, or just to wear around town as a busy mom. Online, this dress was styled with a belt over the elastic – I think it looks great either way. I’m wearing a pair of slip on mules in the photos below, but you could also style this dress with Veja sneakers.

Cecily Dress in Cotton Poplin

Next on the list is the Cecily Dress in Cotton Poplin. If you have a dressier event or a fall wedding this upcoming season, I can’t think of a more beautiful dress! The v-neck paired with puff sleeves feels frilly and feminine, and the slightly a-line skirt is always a flattering silhouette. I prefer the red over the blue floral colorway, especially for fall.

Ruffle-Collar Mini Shirtdress in Cotton Poplin

This ruffle-collar shirt dress is a little preppier than my typical taste, but I’m shockingly drawn to it! The oversized collar would look even cuter untied and unbuttoned too. I would likely style this with the sleeves slightly rolled up and the collar unbuttoned casually, Veja sneakers, and cute gold hoop earrings. Dressing the rest of the look down will help make the peter pan inspired collar feel more chic.

You could dress this down with sneakers or dress it up with a sweater on top for work in the office. It would also be a nursing friendly option because of the button-down front.

Tie-Waist Mini Dress in Chelsea Linen-Cupro Blend

I very rarely ever buy something that is final sale online since I know I can’t try it on. But Hannah convinced me to snag this tie waist mini dress when it was extra sale and I’m SO happy I did! The brown color screams fall, and the gold zipper and buttons add such chic accents. I also love the slightly wider shoulders. The waistline is elastic and also ties for a flattering waistline. The material isn’t heavy. It will work well in the early days of fall where it’s still a little warm during the day. I have a size 4.

Smocked Drop-Waist Dress in Cotton Poplin

This drop-waist midi feels like something that you’d see in the 20s. However, I actually LOVE it because of the smocked top. I do think this is made for someone pretty tall though, since the drop waist works best on a super long torso. If you are tall and work in an office, you’d look amazing in this dress. You could pair it with a black blazer as well.

Gwyneth Slip Dress in Luster Charmeuse

I typically struggle with silk slip dresses like this. I find that they can cling to unflattering parts of the body, but this one is designed a little bit looser and more relaxed than others I’ve seen! Also, I love the idea of styling it with a thin sweater on top. Using this bra trick to make the sweater shorter. This would be a great office outfit if you can dress more casually or perfect for the weekend or even date night with strappy heels.

Ruffle-Hem Shirtdress in Cotton Poplin

I ordered this ruffled shirt dress recently for myself and was so impressed by the details in person! Unfortunately it’s too long on me, so I won’t be keeping it. However, I hope that someone who’s taller than me will snag it for this fall! A shirtdress is always a classic look for everyday or even the office. But the ruffles add such a nice feminine touch to this. I’m 5’1″, so this dress should work really well on anyone taller than me!

I love that you could wear this dress immediately while it’s still hot outside. Then, you could transition it into fall because of the black color.

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