Fall/Winter
52 Comments

Fall Dress Outfit with Peep-Toe Booties

I’ve been on the lookout for some good fall dresses to share with you guys, and this jersey knit shift dress from Old Navy is my latest score. It’s nice in that you can dress it up or down, and the cut is fairly forgiving. Plus it’s just $29 and often goes on sale. (Today it’s 35% off!)

Jo-Lynne Shane wearing a fall dress outfit with peep-toe booties. #fallfashion #falldress

This dress is very soft and comfortable to wear, and the dolman sleeves are a fun detail. I’m wearing the small, and it’s a regular. It also comes in tall and petite, and I probably should have ordered the tall because I expect it will shrink. (I’m 5’5″ for reference.)

I styled it with a workwear look in mind, or I guess this could be a dinner-out look too. I realize not all office situations allow open-toe shoes, but you could wear a closed bootie or a tall boot with this dress as well. It would also look nice with mules or ballet flats if you prefer.

Jo-Lynne Shane wearing a fall dress outfit with peep-toe booties. #fallfashion #falldress

I was actually going to wear these booties with this dress, but then I realized I’ve already styled a dress with them, so I went with these peep-toe booties, which I think are really cute with it for this time of year when it’s still quite warm.

I love peep-toe booties for this time of year when it’s still warm out but you want your shoes to say “fall.” I think the trick to making them look right is to wear them with an outfit that is also a transitional style. This dress has 3/4 length sleeves, so the peep-toe booties make sense. If I had a dress with long sleeves and a turtleneck, the peep-toe bootie might look out of place. I also don’t recommend wearing tights with these shoes so make sure your pedicure is fresh. (And I probably shouldn’t have laid off the self-tanner quite so soon. LOL!!!)

How to Wear Peep-Toe Booties

I recommend sizing down a half size in these booties. The heel is on the higher side, but they’re very comfortable and easy to walk in. Bonus, they’re 20% off!

Jo-Lynne Shane wearing a fall dress outfit with peep-toe booties.This jersey shift dress from Old Navy is just $29 and it's often on sale! #fallfashion #falldress

I accessorized with gold. Aren’t these bordeaux tiger eye drop earrings perfect with this dress!?! I picked them up last week when I was at the mall. I wear a lot of plum and burgundy in the fall and winter, so I know I’ll get a lot of wear out of them.

I also added a gold pendant and some gold bangles.

Old Navy Knit Shift Dress #fallfashion

I often get questions about what shapewear to wear under dresses. I like to wear a slip in addition to medium control shapewear with a dress like this. A slip allows the dress to skim easily over the body and not cling to any lumps and bumps.

A few years ago, I picked up this fitted slip at Nordstrom. It’s pricey for a slip, but I like the raw-cut edges for a smooth fit plus it has a weighted hem so it doesn’t ride up. I wear it under all of my unlined dresses.

The slip has “light control” but that doesn’t do much for those of us with post-child bearing bodies or extra weight we’re trying to hide, so I like to wear my Spanx shape my day girl shorts as well. These help contain the belly pudge (ha!) and provide some shaping through the rear.

Jo-Lynne Shane wearing a fall dress outfit with peep-toe booties.This jersey shift dress from Old Navy is just $29 and it's often on sale! #fallfashion #falldress

As far as this silhouette of this dress goes, I like it from some angles, but I’m unsure about it from others. I feel like it makes me look a little top-heavy with the dolman sleeves adding some extra bulk and making my shoulders look wider than they already are, so perhaps this style is better for someone with more of a pear-shaped body type.

I carried a grey bag with gold hardware (similar here.) I find myself carrying this bag a lot these days. It goes with so much, and it’s a great size for carrying the essentials.

How to accessorize a plum dress with grey and gold.

I don’t work in an office, but this is an outfit I’ll wear to church or out to lunch with friends this fall. When it gets colder, I”ll wear this dress with tall boots and tights. You can also throw a cardigan or moto jacket on top for extra warmth.

Jo-Lynne Shane wearing a fall dress outfit with peep-toe booties.This jersey shift dress from Old Navy is just $29 and it's often on sale! #fallfashion #falldress

dress 35% off // shoes 20% off // bag // earrings // necklace // bracelets // sunnies c/o Maui Jim

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52 thoughts on “Fall Dress Outfit with Peep-Toe Booties

  1. Thanks for the shapewear and slip recommendations!  Being in my late forties, I’m finally conceding to the reality that I may need something to hold it all together, no matter that I’m 5’7 and 112 lbs.

  2. Love the color of this dress! BTW, I use Yahoo and the stretched images don’t seem to be there any longer! ????????
    Have a blessed and productive day!

  3. You look terrific is this outfit!  I appreciate the shapewear details. The KS earrings are gorgeous. How heavy are they?  

    1. They are actually heavier than most of my earrings, I did notice that when I wore them Sat nite. They don’t bother me, but if that’s an issue, be aware that they’re definitely heavier than, say, the KS filigree ones.

      1. Thanks for your reply!  I have two different styles of the filigree type and wear one or the other most days. However, I rarely wear another KS pair that I received as a gift because they are too heavy. They are beautiful, though. I bought some KS Lobe Wonder patches which I hope will help. 

    1. LOL! Well, I already had these pictures taken, but I was glad I had a workwear look going up this week after reading your comment. 🙂 I do need a nudge every once in a while to get out of my comfort zone. 🙂

  4. You look so cute.  Question. I see your nail polish and toe polish are different color. Is that ok?  I have that now but wondered. I wish I felt more comfortable this time of year to do bear legs. Oh my getting older can be hard. Ha ha. You look great. 

    1. It’s totally fine to have different colors, in fact, I prefer having two different colors so it’s not so matchy-matchy. That said, I try to choose two complimentary colors, and I don’t love these two colors together. They don’t clash exactly but they don’t really look good together. I usually go with two shades of the same color, or totally neutral on my hands and then any fun color I like on my toes.

  5. PS the yahoo stretch thing is gone now. :). But the dress doesn’t look wine color like ON site shows. On you looks more purple color. Maybe lighting when you took photos. Cute dress for the price. 

    1. Funny, it still looks stretched in my yahoo account. But I’m glad it looks right in yours. 🙂 I think it is more burgundy in person. The website is closer. My pictures always seem to be a little off with reds/purples/pinks.

  6. You look amazing in that dress! Purple is not usually one if my usual dress colors but I may try it! Thank you!

  7. Super cute outfit on you????. Where’s my fall????  I’m in Pa as well and hating this warm humid weather, enough already…I’m ready for boots and cute jackets…ugghhh…this weather makes me stabby????

  8. You look great in this color as well as the style of dress. I think a faux fur vest would look good with that style of dress (when it gets colder). I just purchased four dresses from Old Navy yesterday with 35% off and an extra 10% considering it was Columbus Day. *Lisa*

  9. Old Navy has some great dresses at such a reasonable price. If I choose to purchase this through your link, do you get some type of credit? Also, is it too late in the season to wear wedge sandals?

    1. Hey Patty, yes, I do. I make a commission when people purchase thru any of my blog links. (So thank you!)

      I don’t think it’s too late to wear wedge sandals if it’s hot where you live, but I’d probably choose a pair that looks more fall. Like, I put away my espadrille wedge sandals and lighter colors, but I kept out the brown ones with a leather covered wedge. I probably overthink these things tho. Ha!

  10. This is a great look! Thanks for breaking the look down and explaining all the parts of the outfit. That sure makes it easy to replicate.

  11. I appreciate your shape wear and slip recommendations. Will treat my daughter. Do you have any recommendations for panty hose. My daughter often needs to wear to her office, Spanx are costly as she gets runs in every pair! 

  12. My favorite color! I agree that the shape of this dress is a bit off for you. I don’t think its because of the bulk of the dolman sleeve or even the width of your shoulders (they’re not wide, btw) . The dress needs to be more of an A-line. It would balance out all of your lovely features. It’s not you—it’s the dress!

  13. That outfit is great on you. You look gorgeous. I just wish Savannah would get out of the 80’s. So hot and humid here. Ready for fall fashions.

  14. I love that you mentioned wearing “shapewear.” Most women IMO benefit from the little layer underneath.

    At my son’s high school homecoming dance last Saturday, it looked like some girls weren’t wearing undergarments of any kind! Yes, they’re teenagers and don’t have bulges, but when did it become okay to leave the house without a bra or underwear?  Times are a’ changin! 

  15. This dress, especially the color, looks great on you! I am excited to wear dresses with tights and booties once it cools off (who am I, a year ago I wouldn’t wear a dress!! Lol)

    Thanks for the shapewear advice. I ordered the slip from your post when I first read it yesterday. Mine is long overdue for an upgrade! 

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