Fall/Winter Fashion
44 Comments

Fall Florals: Old Navy Shift Dress with Ankle Boots

Hello and happy Monday! It’s hard to believe, but Cyndi and I are more than halfway through our 3rd annual 26 Days of Fall Fashion!

Today I’m styling a fall dress. I’m not sure I love this outfit, at least at my age, but it’s a trending look so I’m sharing it and you can make your own decision for your personal style aesthetic. Personally, I feel it’s a little youthful for me.

Fall fashion for women over 40: Jo-Lynne Shane wearing a shift dress in fall florals with taupe ankle boots and glazed leather crossbody.

I ordered this smocked-yoke shift dress from Old Navy. Fall florals are a big trend this season, and I’m seeing a lot of dresses in floral prints right now. This dress comes in several other colors and patterns too.

This shift style isn’t my favorite because it doesn’t have the structure I need to flatter my curves so it ends up looking kind of shapeless, but it’s an easy style that works well for a casual day dress. Since it’s on the shorter side, I didn’t try belting it, but that might work for some women.

Fall fashion for women over 40: Jo-Lynne Shane wearing a shift dress in fall florals with taupe ankle boots and glazed leather crossbody.

For size reference, I’m wearing the small, and this is the regular length. It also comes in tall and petite sizes.

I never considered ordering a tall because I’m 5’5″, but given that it’s a little shorter than I’d prefer in both overall length and in the sleeves, that might be worth a try.

I really like this black floral print. It would look great with black booties or maybe even tall boots, but I wore it with taupe ankle boots to elongate the leg.

Fall fashion for women over 40: Jo-Lynne Shane wearing a shift dress in fall florals with taupe ankle boots and glazed leather crossbody.

I wear these booties a lot with jeans, but I thought it would be fun to try them with a dress. They’re pretty casual in their styling, but I think they work. Another good option is this pair by Sole Society. I really like the clean lines, and they look great with both ankle jeans and dresses, plus they’re less than $100.

I picked up this crossbody bag at the Nordstrom Anniversary Sale back in July. I love the color and the glazed leather for a casual vibe, and it’s currently 50% off! It’s nice and roomy — the perfect everyday size when you need to carry a lot but don’t want a big tote or satchel.

Fall fashion for women over 40: Jo-Lynne Shane wearing a shift dress in fall florals with taupe ankle boots and glazed leather crossbody.

dress (30% off) // booties (option) // bag (50% off!) // necklace // bracelets // nail polish

Be sure to visit Cyndi and see the fall outfit she’s styling today.

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44 thoughts on “Fall Florals: Old Navy Shift Dress with Ankle Boots

  1. I LOVE that dress on you ! Since it is short, maybe you would like it better with a shorter heeled boot ? It would be so cute with OTK boots too. I have ordered a few dresses from Old Navy this year, but didn’t get that style. Seeing it on you, I may reconsider. And fyi, I find that fit very flattering on you 🙂

    1. Yeah, these are pretty low, though. (For me, anyway, haha!) I am wanting to try it with those black OTK boots I got at the #NSale but I feel like that might be overkill. I think it would be cute with leggings too.

  2. I frequently order from Old Navy and often order their dresses in tall so that the dresses are an appropriate length for my age (53) and for my work (at a school).  I go into the store and try them on and if they feel too short, I order the Tall.  This discussion makes me want to go shopping today!

  3. I totally agree with you, it’s too shapeless for your figure; doesn’t show off your small waist…maybe a belt and higher boots?  

  4. I think this dress looks adorable on you!  I don’t always agree with the fitted look, for example, tighter fitting clothing that emphasizes the larger parts of our bodies, as in us larger breasted women.  The flowing look looks great on you , I think.  

    1. I hear you, but there’s a lot of leeway between this and tight. 🙂 I wonder how it would look if a seamstress took it in a bit at the waist to give it some more shape. If it were longer, I might give that a try, but I think this one might get returned. I’d like to try the tall and see how it works.

  5. i ordered my last dress from ON in a tall. I’m 5’6, but dresses there seem to be too short for me, since I’m over 60????

    1. Thank you, Donna. I’m going to try this because I have passed on some really cute dresses due to a shorter hemline that I did not feel comfortable with.

    2. I’m also 5’6 and also order tall from Old Navy often in dresses so that the length is appropriate for my 40-something self…

  6. ON dresses tend to be short on me. I’m 5’8. I typically order the tall if it’s available. Cute outfit! I like the floral print! 

  7. It’s really is a nice look but I can’t seem to feel confident in closed ankle toe boots with dresses? I like them better with the open toe booties to offset my bare legs. But I know they are on trend now, I just like them better with jeans or pants. This dress would also look good with your Vince Camuto black open toe booties as well, in the longer version, since those have a higher heel. 

  8. Hi Jo-Lynn! Just wanted to let you know that when I open my email and get your introduction to your post for the day, the photo of you is elongated. Once I click onto the Read more…, all the photos are normal size. I don’t know if it’s something on my end or yours but it’s been this way for a couple of weeks now. It doesn’t bother me but thought I’d let you know about it. Blessings!

  9. It’s fun to see variety in this series, especially when the trendy look is featured at a great price, and your honesty about how you feel about different looks, as well as discussion on ways they might work better ( ordering in the tall size, for instance) are SO helpful in making wardrobe choices.
    I have tried this sort of outfit before, but it never seems to flatter me. I am tall and have a rectangular, athletic body type that just seems to look like a “box” in a shift dress. The advice about belting this dress and ordering it in the tall size was such a great idea. I am excited to give it a try this way and see how it works.
    Thanks!

    1. I agree, Lori. JoLynne’s narrative about how she makes decisions helps me tremendously. I, too, like that she shows things she’s not crazy about, letting us see what she would change to make the look better.

    2. Yes, try it and see how it works! If you have a straight body type, a belt can work wonders. I don’t usually belt my dresses because I’m so short waisted plus boobs (lol) but I like how that looks on taller, straighter figures.

  10. I like this dress on you, but it’s all about how you feel in it. I’m 57, I think I could pull off this floral print, but not the huge florals. Those that look like a sofa print????. Love the booties. I live on the Gulf Coast, still very hot here! Gives me an idea for making it look Fall. 

  11. I like the overall idea of this look, but I’m like Clinton and Stacey: You can do better. I like the look of the boots/purse with the rich floral print. What I think you could do better on is the dress, itself. The idea of the dress is good, but the execution of this idea by Old Navy looks to my eye kind of cheap–like it’s cut skimpy. Not that it’s too short exactly, but more like they were trying to save fabric and make it on the cheap and it shows. If you could come up with a very similar dress that doesn’t look as skimpy, I think I’d give you two thumbs up. Maybe the tall would be the answer, or maybe a higher quality brand? Dunno. But I really like the overall thing you’re going for! And I do think a shift dress looks good on you!!!

    1. Yeah, I think you nailed it with the quality issue. Old Navy can be hit or miss in the quality department, but a lot of people reading like to shop there and I didn’t want to spend a lot on this style dress. I like their cotton knit dresses, and they have some nice sweaters and tops this year, but I think they missed the mark a bit with this dress. All good input!

  12. Jo-Lynne, I don’t think there is anything you can’t wear….but I know what you mean. I think shift dresses can be very cute, but I like mine to have a little bit of a shape, more tucked in at the waist. To me just that little shift in the outline can take a piece from okay to wow. I love that print and the booties work too. – Amy
    http://stylingrannymama.com/

  13. As I few others mentioned, I would belt this “dress” (I consider it a tunic on my 5’7″ frame) and add black leggings!  Cute print!!!!!

  14. Even though I liked this bag a lot after purchasing it during the anniversary sale, I returned it because I ended up deciding on some other items.  But now that it’s $40 cheaper into my cart it went and hopefully on its way to me.  I bought the Jeffrey Campbell booties and this bag really compliments them nicely!

  15. Belting it with leggings might be a good option. I love the feel of a shift, but you’re right in that they just kinda hang there. I always like booties with casual dresses on others, but when I try it I feel weird…LOL Happy Monday!

  16. I do love the pattern of this dress on you and the booties! I am like some of the other ladies on here and order a tall because ON dresses like these tend to be shorter than I’d like for me and they also shrink. The tall sizes seem to be working better. This is still a great casual look on you!

    Cathy V.
    http://www.cathyvstyle.com

  17. Well Jo- Lynne the outfit is cute but I do agree with your concerns. I’m 5’3 and usually the ON dresses hit at my knee or just above, which is good for my age. I’ve never tried booties with my dresses. My daughter 23 and niece 28 wear that style and so for me to wear  it seems strange lol. I think I would like to try the open toe boot shoe you and Cyndi style. I think that’s more me. Never know until you try something right? 
    Have a great day????

  18. The overall look of the dress is cute, and not to short. However, it looks like something a teenager would wear with the bare legs & booties. I think, tights & ankle booties would be a more put together look and age appropriate. Or, suede pumps & tights would work.

    1. I agree with you. I definitely feel like the overall look of this outfit is youthful. I think pumps and tights would be too dressy, but I can see tights and tall boots with it. It’s definitely something to play around with, but overall I’d like it better in the tall, I think.

  19. I’m sure you will figure out how to best wear this adorable outfit that looks super cute on you!  I do like the idea of tights and a suede bootie.  That brings me to ask the question…are tights in?  Or did the ever go out?  

  20. I don’t know if you remember the dress cinch clip that was big in the 90’s with loose-fitting dresses; you could tuck the back of the dress in and put a dress cinch clip in place wherever you needed to make adjustments. You don’t have to have the dress altered, you can use it on other dresses/jumpsuits, and they always came in pretty decorative colors. I just did a search and yes, they are still available. If you feel “craftsy” you could probably make your own. The dress looks great on you, btw.

  21. Really like this on you, Jo-Lynne, but I know what you mean about it not having enough shape. I run into this problem all the time and I played around with a few brooches that I have. Gathering it a little in the front or back and pinning the right brooch is all I needed! It gives it a little pleating too. I won’t wear a belt because it pulls it up even shorter and at 5’7″, I need all the length I can get. Try it—-it will make all the difference!

  22. I think its cute but agree with everything you and others have said.  I’m thinking it will hang in your closet if you don’t LOVE it.  I just think over all Old Navy doesn’t have the quality and I bet if you washed this it will be even shorter and will hang weird.  But, it really does look cute on your. I don’t think you have to worry about the shape.  Not everything has to fit to show our curves if its casual and depends what shoes, with or without tights etc.  It would be fun to see you do the black leggings or tights and do the high boots and show us again.  🙂  

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