5 Favorites: Dresses

I wanted to do another 5 favorites post this week, but I wasn’t sure where to go next. It seems a little too early to touch on sweaters, we’ve talked a lot about shoes and boots lately, and I don’t wear many blouses or pants… so let’s talk dresses.

For this one, I’m going to speak to general styles of dresses rather than exact items, but I do have some pictures and links of samples in my closet.

My 5 Favorite Dresses

#1. Classic Sheath 

A structured sheath is hands-down my favorite dress silhouette. It is by far the most flattering style for my hourglass shape, and I usually have a couple in my closet at any given time. My current favorite is this Tonya Pleat Dress by T Tahari, and it happens to still be in stock at Bloomingdales!

It has a great structure to it so it’s super flattering, plus it’s fully lined. The narrow v-neck is modest and flattering, and the pleated detail is a nice touch. This is a dress you can wear a blazer over for the office and then remove it for more of a dinner look. It also comes in handy for funerals, which tend to happen rather suddenly so it’s nice to have a go-to option for that.

The styling options for a black dress are virtually limitless, but I’m always partial to leopard pumps or strappy sandals for a date night look. For work, nude pumps look great with a black dress and are more modern than black, although black works too. When I wore this dress to a funeral last fall, I wore black pumps because it seemed more appropriate somehow.

For summertime, I’m a huge fan of a linen sheath. They work great for church or other events like baby showers or weddings. This year I’m loving this embroidered neck sheath. It comes in navy and black and is on sale right now.

#2. Wrap Dress

I also like to have a wrap dress in my closet, usually in a print. These are generally summer dresses for me, but sometimes you can find them with 3/4 or long sleeves for winter, and you can always throw a cardigan or blazer over top a short sleeved dress to make it more year-round appropriate. This navy and white polka dot wrap dress is still in stock, and it’s a nice one for summer.

I also have and like this one but it is no longer available. For some reason, I’m drawn to wrap dresses in bold prints.

#3. Sweater Dress (fall/winter)

I love a good sweater dress in the wintertime. Last year I had this teal one from LOFT, which I wore with booties in the fall and then tights and tall boots when it got colder.

Must Have Sweater Dress for Fall - only $39!

SALE ALERT >> LOFT is running 40% off everything with code OHYES. See some of my top picks HERE.

I also picked up this one at Ann Taylor, and I wore it to church a few times with boots and tights. Neither are currently available, but as more fall styles arrive in the stores, there will be more options.

#4. Casual Knit Dress

It’s always nice to have a few casual dresses you can throw on with sneakers or sandals and then top off with a sweater or jean jacket if you need some extra warmth. I tend to like knit dresses for this purpose, and right now I love this striped tank dress I found at Nordstrom a few weeks ago. It comes in green, blue, black, and solid black, and it’s fully stocked.

I’ve also styled a couple versions of this Old Navy 3/4-sleeve shift dress. They don’t have one in stock right now, but they usually carry some version of this in spring and fall.

#5. Printed Shift Dress

I usually have one or two shift dresses in my fall/winter wardrobe because they pair nicely with tights and boots when it’s cold out or pumps in milder weather. I’ve passed on the few I had because they tend to be memorable and I’d already worn them quite a few times, so I’ll be on the lookout for something new this fall.

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Well, I guess that was a few more than 5. LOL! For a girl who doesn’t love dresses, I sure did come up with quite a bunch to share.

Before you ask, no, I don’t really wear maxi dresses. I’ve had some in the past, but I didn’t have one this summer. I tend to prefer knee-length dresses. I find them easier to wear and they don’t seem as fussy, but I know a lot of women who can rock a maxi dress so I’m not saying no one should wear them. They’re just not my personal favorite. The swing dress style is also cute on others but doesn’t do much for me, and a fit-and-flare or A-line style is great for women with more of a pear shape.

With dresses, you really have to know what works for your body type and stick to what looks good on you regardless of what is trending. But then again, that’s probably true for all matters of fashion. I’m just happy sheath dresses are plentiful right now!

Speaking of knowing what works for your body type, registration for the next Adore Your Wardrobe course will be opening soon. I’ll keep you posted, but if you’re curious or want to get on the waist list, you can find out more HERE.

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51 thoughts on “5 Favorites: Dresses

  1. I know you’re probably tired of hearing me say this, but you really wear dresses so well, Jo-Lynne!!
    I love the fact that you don’t have to match the top to the bottom with them—easy, peasy!!
    I do like the maxi’s at times, because then I don’ t have to worry about shaving my legs–ha ha! Although I have one that is a little shorter in the front than the back, and it’s way easier to walk and climb stairs in….

  2. First of all I have to say, you look stunning in each & every style! And that navy dress……❤❤. Such good info on the styles. Sadly, I don’t see women in dresses much these days. We have a small country church, with a number of women that have never worn slacks to church, but after an especially cold winter a few years back, there were some converts!! It’s nice for you to show us all the options available out there!

  3. I think it’s interesting that you find maxi dresses fussy, Jo-Lynne. I never thought of them that way. On a hot day, I love a maxi to go shopping, wear to a Sunday afternoon baby shower, or even run errands. And this year I’ve been wearing an older one over my bathing suit when I go to the beach. I don’t feel quite so grungy running into Wawa after a day of fun, sun and sand. I tend to go with the simple tank styles in cotton so the fabric is heavy enough not to show panty lines. The best part about a maxi is that it’s ok if I didn’t shave my legs! The downside is that it’s tricky to find the tank styles that don’t require a strapless bra. That defeats the purpose of a comfy dress to throw on on a hot day!

    1. I think it’s a combination of bra issues (most maxi dresses seem to create bra issues) and then they tend to be clingy (in the wrong places.) But overall I just don’t care for dresses unless they have a lot of structure, and most maxi dresses don’t. It’s a personal thing. I like them on other people.

  4. My favorite is #5, the printed shift dress. I love the 3/4 sleeve and those boots! It’s a more casual dress vibe but your right you have to be careful how often you wear a printed (memorable) dress. Another dress I liked but you didn’t mention this time is the v-neck tshirt dress from Old Navy. I ordered the grey after you posted it with the white jean jacket and boy do I get a lot of wear from it. It has a nice stretchy soft fabric and comes in several colors. Plus it’s on sale now and comes in petite ???? Thank you for sharing that one!

    1. I loved that one too and ordered it in my usual size and it was wayyyy to clingy and I didn’t know if next size up would work for paying more shipping and if didn’t out the money again. The store close to me didn’t have that style. Did you size up? I’m 5’3″ and didn’t order the petite and I liked the length on me. I found tank style similar at Macy’s and thinking of ordering another, as its so comfy. 🙂

  5. I prefer wearing dresses, I use to wear maxi dresses, but for some reason this summer I was just so over them, and took them to our local thrift store. This is a Christian ministry from the re sales it helps the community food bank, pregnancy center and so on, so I don’t mind taking my items there not only do they take clothes but all kind of stuff.
    Any way I do have one question I bought a little dress that hits me at mid thigh and I love it but everyone else hates it cause they are use to seeing me in the knee dresses like you have on, so instead of getting rid of it only wore it twice, is there any way I can wear it that would not make it look like not me?

    1. I think that’s a hard length to pull off at our age, honestly. I would definitely wear with flats but it may just not be a good look. It’s hard to say without seeing it on, tho.

    2. That is hard length 40 yrs. on. 🙂 If you ever look at Cyndi’s blog, she sometimes post with leggings and she likes Glamour Farms online shopping and they style a lot of tunic type dress/shirts with leggings and jeans. You might go to their sight and get some ideas. I like to look at the sight for fun. The ladies are so country, southern and so cute. I’ve ordered about 5 things from them and all of them I’ve liked, but they do have expensive prices and shipping for the quality, but they do lots of sales too. I watch for sales and no shipping. Items do go fast though. Be sure you go over their return policy first. I can find better quality clothes and price at Loft.

  6. I’m with you on dresses…don’t wear them much. I’m definitely a jeans kinda girl.

    Yes, school starts this week in our county. It’s early, but this way the semester is over before Christmas break. We also get a full week off at Thanksgiving, and a 5 day weekend at the quarter break. School will be out in late May. Only problem is PE and recess time….it’s just soooo hot in Florida this time of year. Our feels like temp yesterday was 110!

    1. That would be kind of nice to break it up like that, but yeah, it is so hot right now to be going to school. I would hate that, I think. To me, back to school time was always fall.

  7. So many cute dresses! You look great in all of them. May I ask what size you got in the top 2 sheath dresses? I’m between a 6 and an 8 and I know you are as well. I’m loving both of those and I need a black dress. Thanks!

    1. I’m an 8 in both. I would say the black one runs a tad small. I haven’t tried it on since I put on 5 lbs (lol) but it definitely runs a little small. I’m always an 8 in Eliza J.

  8. Another week of summer break sounds luxurious! I live in Colorado and our district is the earliest to start in the state which was Aug 1st!! We do however have 2 week breaks throughout the year. So when some district’s start after labor day, we have a 2 week break coming up in Oct. It’s nice because we’ve gone to Disneyland during that time and get great rates because it’s off season and it’s never busy because everyone else is in school. I do miss the ‘lazy dog days of summer’ in Aug with my kids.

  9. Love, love. The first dress and you’re rockin’ the shoes! You’re such an inspiration!
    Thanks. Every day! MaryBeth

  10. I think you look great in all of the dresses you shared, and you have a nice selection in your closet.

    Regarding your hair: You know it will grow back if you shorten it some. And you might find an extra spunk in your step if you were to change it up a notch. Step out of your comfort zone!

    Some GA schools started mid last week, then most others joined in this week. I am a GA native, grew up in the metro Atlanta area. We always started to school after Labor Day, we got two weeks off for Christmas, I recall being off a couple of days for Easter, and we had three months off for summer. It’s definitely not that way any more. There are numerous one week breaks throughout the school year, thus they have to return to class sooner to ensure they get the required number of days in class. This is another time I’m glad I’m older and done with that.

    Be blessed!

  11. You look great in all of them! I have trouble wearing the sheath – although I love the look (I used to wear them when I was younger and thinner 🙂

    I’ve found a few cute A-line knit dresses with embroidery for fall… anxious to wear with my utility vest or cargo jacket!

  12. I love these dresses The Sheath dress is very pretty. I wonder about the Fit and Flare Dresses as an option

    1. Fit and flare dresses are great on women with more of a pear shape because they skim over the hips and show off the small waist, and they also can work for a carrot (inverted triangle) because they balance out a larger top half. I don’t usually like them on me, for some reason, but every once in a while I find one that works. It depends on how the top is cut.

  13. I have to agree you look great in dresses! You should like them more!!

    I love dresses because of the one piece and done theory in getting ready for work. Although I do often throw a cardigan over them because my courthouse is usually cold. I’m a huge maxi dress/skirt fan. They are so comfy to me. But I’m about 5′ 7 1/2″, so maybe they work better on me. You sure do dress your body type well because I always think you are taller than your stats suggest!

    Oh, and have a wonderful day!! 🙂

  14. ILove, love love the LBD! And I adore the black strappy sandals you’re wearing with that dress in the first pic. Where did you buy them and are they even available anymore?

  15. Great post Jo-Lynne! I have always had a love for dresses and skirts. And, thanks for reminding me to change my hair appointment! HaHa!.

  16. First…..your hair always looks great, but if you cut just a little off, it usually helps bring the spunk back and make it looks thicker. 🙂 You look great in all the dresses. I agree with everyone……you should wear more dresses, as you look so good in all of the ones you have. 🙂 But, I agree. When I wear them, I feel so dressed up compared to others. Our church is small and people have gotten so casual and so when I do where a dress, I feel I stick out. I do wish we’d go back to “church” clothes again. I do like the more casual though when the Winter months hit. Its too cold then to wear dresses all the time. I don’t know if I have a favorite one you styled. They all look great. You should keep your patterned dresses, even if you think they are more memorable. You can always put a different color cardigan with them or something. But, I am the same way when I buy anything patterned or floral.

    1. I agree with the hair, I always feel like it looks thicker after I get it trimmed. Even the color helps, I think. I just have a few spots that are thinning out on the ends. It is so annoying. She always tells me I have a ton of new grown, so it’s not thinning in the crown, like some women do. But the ends get really thin and wispy, especially towards the front. A few years ago I had to shop it and I hated it short. I am hoping that doesn’t happen again.

      I also agree on the church clothes issue. I really wish people still dressed for church. I assume they do in some areas, but our church worships in a school gymnasium so I think people just figure, why bother. LOL.

  17. PS Could you give me link to the front tie short sleeve sweat shirt you style on instagram, from GAP. I don’t know how to do the like to know it. Thanks.

      1. That GAP top is cute! Can you tell me what size you chose?

        I love all of the pretty dresses you’ve shown. I like dresses and need to wear to wear the ones I have. They tend to hang in the closet.

  18. As everyone else has said, you look great in all of the dresses! I thought I was the only female left that doesn’t wear maxi dresses! ???? I love them in others, but I look so matronly in them. I’ve asked Stirch Fix for a sleeveless black maxi to try, so we will see. I love your hair and think it always looks beautiful. School starts for us on 8/23. ????

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