UPDATED more pics- How to style th(ese) dress(es) without looking like a church lady

(Update at the bottom...more dresses)

I promised some pics of my adventures with trying to add dresses into my wardrobe. I am sure there will be more posts but for now, I could use some help! This dress is comfy and (I think??!) flattering but I look too much like a church lady for my tastes and need help with styling.

If it matters, I'm 39 and my workplace is pretty much anything-goes. That being said...

1. This dress is too low cut for work. I'm wearing a slip that looks like a cami on top. Is that okay?

2. Dress on its own. Church lady city!

3. Dress with leather jacket and slingback booties.

4. Dress with denim jacket and slingback booties

5. Hard to see, but pointy toed flats (same dress and jacket)

Do any of these work? Other suggestions welcome!

(Update)

Added some more dress pics. The coral dress and the pink (in person it's kind of a muted rose; ALSO I'm not wearing any undies with it, and no slip lol, so IRL I'd look less...lumpy in it.

More styling ideas appreciated because I can't wear a denim jacket every day, and a couple more questions:

1. Can I wear wedge pumps with a dress (such as pic 10)? Or would they look too "heavy"?

2. What other types of jackets would you suggest to keep it casual? A blazer would be easy but formal. Maybe a moto? I had a moto but I need a new one because it's way too small now

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7 years ago

Jaime

(website)

Veteran

Looks like a nice dress, and not particularly church lady to me (but what do I know!), but the denim jacket definitely works to make it casual.

shoppingisfun

Thanks for the input! I think it's the print maybe that is making me think church lady and/or kindergarten teacher. Not that there is anything wrong with either of those things but it's not really the look I'm going for I want to look halfway young and trendy lol

rachylou

You look young I don’t see church lady, but I can see kindergarten teacher... of the young, sweet variety. The cami is good - esp because it’s black (more modern than white). I like the leather jacket and shooties with it; that’s sophisticated.

Anonymous

You will notice that these days most ladies at church are not wearing dresses. There are more in pants or jeans. Your outfits all look good, especially the ones with a jacket. The cami- looking slip looks fine. The sling back booties look modern but I like the pointy flats too.

Jessikams

I think the dress is cute, fits well and looks useful and versatile. All the jackets you’ve used look just fine. Maybe for a more trendy look you could try making it more “maximal” and using a patterned topper, also in the same palette?

Jane

I like all the outfits but especially with the denim jacket.

Cardiff girl

I m itching for you to add some colour to these outfits like maybe a scarf ,some jewellery or coloured shoes and bag .lts a nice dress and I like your toppers.

Mainelady

What Cardiff Girl said. I don’t really see church lady. The dress looks great on you and I think adding the denim jacket elevates the look.

jussie

I like the dress just fine how you’ve styled it... but you could try it with some black combat boots to give it some 90’s toughness. Or some kind of canvas sneakers to go for a contemporary casual look.

Angie

Fashion Stylist

YOU DID GREAT. All renditions are fab.

I'm with Jussie too. Try flat boots and sneakers. Maxi cardigan.

Bijou

A great dress, I like how you are wearing it and do like the idea of toughening it up with boots. For this reason, the version with the leather jacket is my favourite.

Kathie

Looks great with the jackets and the sling backs. The flats are a bit more of a “sweet” look. I think you’re on the right track to toughen the look with booties, or other more substantial shoes.

Yes they both work well, and i agree with trying a maxi cardigan over it also. Tall boots will work well with it for winter. If you wear cognac try that too!

Thanks for the replies! I was already planning on getting some new scarves (my current collection is less than fab) and I definitely need to up my shoe game. I have few that seem to work well with dresses (makes sense since I bought them all to go with jeans or slacks) other than sandals or tall boots! It's currently too cold for sandals and too warm for tall boots lol.

I will try to post some more looks this weekend. I bought 4 dresses and they're all basically the same shape...I guess you would call them A-line? I don't even know the terminology!

JAileen

I like the outfit with the leather jacket and the shooties. It’s a great outfit, and not too church lady or kindergarten teacher.

Christina F.

For the first dress, I love the leather jacket one the best, but these are all good looks. Church lady look averted!

I like 6-7 too with those flat shoes. I like the shoes in 9 with that dress better than the ones in 8.

Thanks for the replies! I think maybe a shoe with animal print might work with one of the solid color dresses? I have a pair of snake-print low wedges I might try later.

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