Now and Later: Fall Outfits With a Dress + More Comfy Pieces!

Two Fall Outfits with a Dress

I know we are all split on whether you’re still in 80 degree weather (??‍♀️) or are already experiencing cooler temps. No matter where you’re at weather-wise, today’s post is for you!  I’m showing you two fall outfits with a dress and talking through how to style one for the warmer part of fall AND once it cools. And I’m partnering with JCPenney to do it!

JCPenney carries just about everything, so it was reallllly easy to find the right pieces to mix and match.  Aside from carrying everything under the sun, they offer a wide range of sizingmisses, petite, plus, and tall! Plus they’ve got pieces for women in all different age groups and styles. Oh, not to mention the price points at JCPenney are ??! I found some amazing, comfy pieces there that are incredibly affordable that I can’t wait to show you!

Two Fall Outfits with a Dress

SIZING INFO: I’m 5’6″ and usually S/M or 6/8 in clothes, 8.5 to 9 in shoes.

Today I’m styling this floral print dress for “now” meaning warmer weather, and “later” for cooler weather.  (If the “now” and “later” doesn’t coincide with your weather, just go with it.  You get the idea.  :P)

This dress is suuuper comfy and stretchy, plus it’s totally nursing friendly cuz of the cross-front! ?? It’s got an empire waistline so it has some shape.  One note–there are some pleats below the bust which may be flattering and pull away from a tummy or could make it look like you have a pooch. Typically I find it is in relation to how large of a chest you have.  Anyway, just a heads up.  Otherwise, it’s a super comfy dress and can be very flattering. OH! And it’s veryyyyy inexpensive, especially during one of JCPenney’s sales! I got it for $14.99!  Find it HERE. I’m wearing size S.

Utility Vest + Floral Dress + Taupe Lace up Sandals + White Necklace Utility Vest + Statement Earrings + Navy and purple Dress + Tan Bag Navy Print Dress + Green Utility Vest + White Necklace + Tan BagBlock Sandals + Green Vest + Blue printed Dress + Tan BagUtility Vest + Statement Earrings + Pendant Necklace + Dress

For the warmer weather look, I paired it with a utility vest and heeled sandals with thick straps.

A utility vest is a fantastic option for warmer fall weather! It takes the place of a utility jacket when it’s too warm for full sleeves.  This one is thin so it won’t make you too hot, and it is amazingggggly soft!! Plus it has drawstrings to cinch at the waist for a flattering fit, and it has large pockets to hold all your stuff. Great way to remedy not having pockets when it comes to dresses!  I’ve seen this at various prices depending on the sale, but always, always, always worth it.  It is seriously an amazing piece!  If it’s out of stock in your size, check often. Within the last few weeks I’ve seen it go mostly out of stock and then completely back in stock. If you’ve been looking for a utility vest, I highly recommend this one!  Get it HERE.  I wear size XS. Runs pretty oversized.

Instead of a peep toe bootie, I went with a heeled sandal, but one that has thicker straps and is more “enclosed” if that makes sense.  Put together with everything else, it’s a tad more “fall” feeling, covering more of my foot, but is still a sandal good for warmer weather.

Shop the Outfit:
Dress: c/o JCPenney (exact–size S)
Vest: c/o JCPenney (exact–size XS)
Shoes: c/o JCPenney (exact–size 9)
Bag: c/o JCPenney (similar)


Printed Dress + Maroon Cardi + Booties + Statement Earrings + Tan Bag Taupe Booties + Maroon Cardigan + Printed Dress + Tan handbagMaroon Cardigan + Printed Dress + Tan Bag + Pendant heeled booties + dress + Cardigan + tan handbag + pendant necklace

For “later,” I styled the dress for mid-fall when it’s still not totally chilly.  I layered on this super soft and stretchy cardigan, which is another piece that feels great at a very affordable price!  It comes in multiple colors.  See them HERE!

If you’re looking for an inexpensive option for booties, these have the dip in the front which I’ve said before elongates your legs.  (See THIS post for what I’m referring to.)  Heads up, with less expensive booties be mindful that they may crease where the toe bends due to the materials they’re made of.  But if that doesn’t worry you and you want a cute, flattering, affordable option, try these HERE!  They come in the “sand” color I’m wearing above, black, and an olive-y brown.

When temps truly dip towards late fall, easily layer up this look with tall boots, tights, and an oversized scarf!

Shop the Outfit:
Dress: c/o JCPenney (exact–size S)
Cardigan: c/o JCPenney (exact–size S)
Booties: c/o JCPenney (exact–size 9)
Bag: c/o JCPenney (similar)

Be sure to check out JCPenney as you build your fall wardrobe!  You can find some truly comfy pieces there at extremely affordable prices!

Created in partnership with JCPenney



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