Try On Haul: Summer Dresses

Hi friends, and happy Friday! We’re headed home today; it was a quick trip, but we had a good time despite the rainy weather. This week’s Try-On Haul focuses on summer dresses. It started with the travel dresses I’ve ordered, but I ended up including some others as well since I had the pictures.

SIZING NOTES: I’m 5’5″ and I usually wear a small in tops and dresses, a 29 in jeans, and a size 8 shoe. Gifted items are indicated by c/o; everything else I purchased myself.

Columbia Freezer III Dress

at Zappos (M) // at Amazon (M) // sandals (39)

You may remember I shared this Columbia Freezer Dress in one of my other Try-On Hauls. I like how lightweight it is, and that it’s moisture-wicking, but I didn’t love the cut, and I really dislike the white triangular label in the back. I know it’s a small detail, but it really bugs me.

One of you suggested the Columbia Chill River Dress as an alternative, so I ordered it…

Columbia Chill River

at Kohl’s (M) // at Zappos (M) // at Amazon (M) // sandals (39)

I like how this one has a straighter cut to it, and the higher neck + UPF 50 will protect my chest from the sun. (I have a lot of sun damage because I always burn there when I wear v-neck tops. I sunscreen my face religiously, but often forget that area.) It also doesn’t have that annoying white triangle in the back.

It’s super lightweight and will pack down to nothing in my suitcase, and the solid black is super versatile. I can easily wash it in the sink and hang it on a hook, and it will be dry in a matter of hours. I can see myself wearing this several times during our trip, which leaves more room in my suitcase for makeup!

VERDICT: Definitely keeping this one. I already put it into my closet.

Z Supply Cara Rib Dress

at Evereve (S) // sneakers (39)

While I’m sharing casual little black dresses, this one came in my last Evereve Trendsend Box. I almost didn’t even try it on, it looked so tiny, and while it looks better on than I expected, it’s definitely not for me. I wish it were longer because I really like it otherwise.

VERDICT: Returned it.

Eileen Fisher Organic Cotton Knit Tank Dress

at Nordstrom (XS) // sandals (8) //  similar earrings

This is a dress I have from last year, and I’m throwing it in here because it’s still available, and it’s definitely one I’m planning to bring to Italy. I wore it a ton last year, and because it’s a high quality stretch cotton, it looks more elevated than the Columbia activewear dresses.

I’m a huge fan of Eileen Fisher dresses. They’re expensive, but they really hold up, and they’re highly versatile. I discovered these during the 2021 #NSale, and now I keep an eye out for new styles. Speaking of which…

Eileen Fisher Scoop Neck Tank Dress

on sale at Bloomingdale’s (S) // sandals (8)

I was drawn to this one because it looks light and airy, and it’s a silhouette I don’t currently have in my closet, but I feel like it swallows me up and looks rather shapeless.

VERDICT: I could probably wear it a size smaller, since I often wear XS in Elieen Fisher dresses, but I sent this back and didn’t bother to re-order in the XS. I have several solid black dresses, and I don’t think this silhouette does a whole lot for me.

Eileen Fisher Tiered Pleated Silk Midi

at Nordstrom (XS) // P448 sneakers (39) // Pia wedge sandals (8)

This is another Eileen Fisher, and I almost didn’t even order it due to the price point, but then I decided to try it because I was curious. It’s 100% silk, and I think the crinkle texture is really fun. It’s also great for packing because you really can’t wrinkle it. It actually arrived tied into a loose knot inside the shipping box!

I wanted to love this, and I thought I did at first, but when I put it on for my husband and daughter a few days later, both of them told me it was shapeless and made me look bigger than I am.

VERDICT: I feel like it would be a nice option to have, and it can be dressed up or down, but given the price point, I decided this one belongs in the “if in doubt, do without” category. It went back.

Eileen Fisher Sleeveless Jersey Dress

at Neiman Marcus (S) // at Nordstrom (S) // sandals (7.5) //  similar earrings

This Eileen Fisher dress was the winner of the bunch! You may have seen this one before, since I already photographed it, but I think it’s worth including here because it’s a keeper.

It’s such good quality, and it has a really nice drape, even though it’s a simple cut. There’s definitely more to it than meets the eye. I think I’ll get a lot of wear out of this one.

VERDICT: Keeping!

Evereve Maia Dress

at Evereve // Kia sandals (8) // earrings

This dress also came in my Evereve Trendsend Box. It’s cute, but I’m not usually one for ruffles, and it’s sooo short. Way too short for my comfort level these days. I do like this color, though, and the style is really cute if it aligns with your personal style.

VERDICT: Returned it.

Sleeveless Splitneck Mini Dress

at Gap Factory // Kia sandals (8)

This dress is a similar style, but from Gap Factory. It’s a more comfortable length for me, but the fabric is super thin, and I just don’t see myself wearing it.

I mean, I could maaaaaaybe see pulling it out for dinner one night in Italy. It might be fun to step outside of my comfort zone and wear something different, but I don’t see myself wearing it enough to warrant taking up a hanger in my closet. It went back.

VERDICT: Returning.

Plaid Midi Shirtdress

at Gap Factory (S) // Kia sandals (8) // earrings

This is another Gap Factory dress that went back. The colors are fun and summery, and I like that it’s a different style for me yet still somewhat classy and understated, but it doesn’t do much for me.

I played around with the tie at the waist, trying different placements and cinching it tighter, but I still feel like it hides my curves and makes me look boxy. It’s also kind of stiff and not a comfortable fabric to wear.

VERDICT: Returning.

Gap Factory V-Neck Dress

at Gap Factory (S) // Iman sandals (8)

Now, this one, I might keep. I have the black one, which I styled in this post, and I thought the blue and white might be a nice option for Italy because it’s lighter and doesn’t look like anything else I have. My husband and daughter both think it would make a better pool coverup… but I think it could be both!


Lululemon Classic Fit Cotton Blend Dress

at Lululemon (8) // Taos sneakers (8.5)

I can’t remember how I came across this dress, if someone recommended it, or if I fell down the rabbit hole clicking on links. I don’t usually go to Lululemon, so I feel like someone led me there, but anyway! This dress is a nice one if you want performance apparel that doesn’t look and feel like performance apparel.

The Columbia dresses are great, but at the end of the day, they look like activewear… which is fine for sightseeing on a hot day, but I prefer one like this that looks more like regular street clothes.

My only complaint is that I wish it came in more colors. I feel like this pink washes me out, I don’t want another black dress in this style, and the linen and java colors are kind of drab. I do wonder if I should try the 10; this one fits, but just barely. I wouldn’t want it to shrink at all.

VERDICT: Deciding… I might re-order the 10 to try.

Sleeveless Matte Jersey Twist Dress

40% off at White House Black Market (8) // Marc Fisher heels (7.5)

Now this one was a nice surprise! I believe I saw this recommended in another travel facebook group, maybe Fashion Travel Girls? I’m also a part of a few Italy travel groups, and I can’t keep track. But this one will be nice if I want something a little bit fancy. Maybe when we go wine tasting in Chianti…

I feel like the neckline and cut of the shoulders is really flattering on me, and the knotted detail at the waist helps accentuate my waist, which seems to be getting lost in a lot of the dresses I’ve tried lately. It’s also nice for travel, in that it doesn’t wrinkle or take up much space.

VERDICT: Definitely planning to keep this one! I do need to try it with flats, though. I’m not sure I’m bringing heels to Italy, although if I do, it will be the pair I’m wearing here because they’re lightweight and low volume.

Maggy London Floral Print Ruffle Smocked Maxi Dress

at Nordstrom (10) // Marc Fisher heels (7.5)

This one isn’t really a contender for Italy, but I ordered it to try for the wedding I’m attending in June. It’s okay, not unflattering per se, but too froo-froo for my personal taste. The fabric also feels cheap, which I could overlook for a single-use dress, but I think I can find something I’ll feel more confident in. I want to feel like me.

VERDICT: Returning.

Maggy London Short Sleeve Midi Sheath Dress

at Nordstrom (8) // Marc Fisher heels (7.5)

This one is way more flattering and definitely more my style, but the rick-rack trim and length of the sleeves looks a little mumsy. I also didn’t like how the lining was hanging out of the front of the skirt. I don’t know what’s going on with Maggy London; this brand used to make a nice quality dress at a moderate price point, but I’m not terribly impressed by these.

VERDICT: Returned it.

And that’s all I’ve got for today! Not a lot of winners in this batch, but when it comes to dresses, I have to try a bunch to find the ones that work for me, especially with the frilly styles that are currently trending.

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63 Responses

  1. Just ordered Eileen Fisher sleeveless jersey dress in Ocean blue. Love how it looks on you. Ordered shorter black one last year after seeing it on you and it us an amazing dress! I was hesitant bc of price but definitely high quality classic piece!

  2. Remember, if you are sightseeing in any of the sleeveless dresses, make sure you have a scarf or something to cover your shoulders for going in churches.
    Those heels will probably not be a good choice for walking around on cobblestone streets in Italy. I would use a solid, wedge sandal, or better yet, use your flats, and save the space in your luggage!
    Also, since you were trying to do carry-ons only, do not over estimate the amount of times you will actually change into a dress for dinner. If you’re already looking a bit put together for sightseeing, frequently, you are so tired by the end of the day that you just want to eat and go back to the hotel, not go back and get dressed for dinner.

    1. Exactly this 100%. I was thinking the same thing from my personal experience. It’s very very rare that I change clothes throughout the day while traveling. Also, Jo-Lynne you’re putting a lot into your travel pieces, I always track what I’m thinking of buying to take on a trip to how it translates to my daily life at home.

      1. Yeah, I often change for dinner, but it might be different on this trip. I still think having one nicer dress is a good idea. As for the heels, yeah, probably not worth taking up the suitcase space, but I have this strange feeing I’ll get there and wish I had the option.

        As for travel pieces, I don’t wear a lot of dresses in real life, so I will need more for this trip than might make sense for daily life at home, and I’m fine with that. And maybe if I have them, I will find more opportunities to wear them, but if not, and they make my life (and packing) easier on this trip, I will just donate or sell afterwards.

        1. You may wish you had them, but that feeling will pass. And if not, then you have an excuse to buy a new fabulous pair of Italian heels 🙂 On my recent trip, I felt the need for a nicer purse sometimes at night, instead of my Travelon. Three new purses later…. LOL

    2. 100%. The best laid plans. Once you are there and out touring you just don’t want to waste the time to go back and get ready to go out again – especially with 5 people. When we did France for 2 weeks I think we changed for dinner ONCE – a night we had a Seine dinner cruise booked. Otherwise – its all about comfort, beating the heat and remember – yes, you have to feel good about yourself but No One else is looking at you and what you are wearing. With carry on only (good for you – I couldn’t do it) – i wouldn’t even consider taking a heeled shoe, not worth the space for the maybe once you would wear them. I would take a 2nd pair of slightly dressier flat or almost flat comfortable sandals instead.

      1. Yeah, you’re probably right. I wasn’t planning to bring any heels until I found that dress. I’ll have to see how it looks with the strappy flat sandals I usually wear when I want something a little dressier but still flat.

  3. Hi, you mentioned you have a wedding in June. I have 3 so would love to see you feature wedding guest dresses. I have ordered several and returned them all. They all looked so cute on the models but were not flattering on me. Maybe you could suggest the best dresses for body type. I am 5’3, short waisted, and straight body.
    Love all your posts by the way!

  4. Love your adjectives to describe things…..made me laugh while drinking coffee (that maybe too mumsy as well). You do a great job, and you have to love your audience of opinion….at least they’re honest.
    My pet peeve in the summer heat is I sweat on my back sometimes (not under the arms) so I’m always trying to take that into consideration with clothes/colors etc that don’t show that (and if you add a knap sack etc while traveling). Yes to moisture wicking when site seeing……

  5. Loving the gold/beige sandals you have on with the Chill River dress, except your link takes you to a different pair of Taos sandals. What brand/style are they?

  6. Happy to see a high neck dress. This is my challenge for summer now as I have sun damage and need coverage on my neck and updating for everything to be high neck. That could be a post…

    Alas, v neck just looks so much better on me.

  7. Thanks for trying so many dresses. I too have been having a problem with dresses. I don’t feel myself in the frilly, ruffle styles, even though I’m drawn to them, seeing them on others. Agree with all your assessments. I always wondered why they make the more sporty dresses in polyester. It seems like a hot material to me for hot weather. It does say moisture wicking but still. You have a lot to do getting ready for this trip and your blog, but nice you can feature vacation wear for us as you order. Safe travels home. Today busy day for me getting ready for all my kids and grands coming from out of town for 3 days.

  8. Omg you have amazing legs! The shorter dresses are so much more flattering on you. My suggestion would be to keep the black one and see if you can become more comfortable in it, because your look awesome 🙂

    1. Why, thank you! I would rather find one with fewer ruffles. I always loved a sheath with a hem an inch or so above the knee, but they’re hard to find right now. I guess I could hem one if I find one I love, but that look seems dated to me at the moment.

        1. Ahhhhhh… Yeah, I didn’t feel good in that one – in that size, anyway. But I was looking at the way the pink one fits the model, and I wonder if I should try the medium.

    2. Totally agree. Jo-Lynne that shorter black dress after the blue one looks amazing. You can definitely still rock the shorter dresses!

  9. I’m intrigued by the Taos sneakers. Are you keeping them? Are they as comfortable as the other shoes you wear?

  10. If you haven’t already, you may want to check out Backcountry. Lots of sporty, casual and some dressier dress options from brands like The North Face, Patagonia, prAna, Kuhl and more.

  11. I still like the Eileen Fisher tank dress from last year, don;t care too much for the athletic type dresses. The black and white print longer dress looks so nice on you, love that one.
    Now the plaid one, with a few alterations and addition of pearls and heels could look a little like June Cleaver with that 50’s vibe! lol

  12. I love dresses, but I find I’m wearing less of them now since church is so informal. And in my old age, I don’t wear dresses very often in cold weather! But with warmer weather around the corner, I’m open to a dress or two. I loved the black & white matte Jersey twist dress….that may be a purchase. I’m happy for you to get to go on your Italy trip….how exciting! Have a blessed Good Friday!

  13. With your dark hair, I think you look great in the Lululemon Classic Fit Cotton Blend Dress, in that color. It would be something different for you. And I’m really glad that you kept the sleeveless Matte Jersey Twist Dress! It is a beautiful dress that you look great in!

  14. Gotta weigh in here… I might be an on island when I say I love the Eileen Fischer black crinkle dress! It’s so pretty and feminine without the frills. And I also like the LLL rose colored tank dress, the WHBM twist front dress screams Italian vacation to me, and the short black Gap Factory one is super cute for sitting outside sipping on a cocktail overlooking Lake Como! 😄. My advice for your Italy trip is to stick with what you would normally wear in the summertime with the mindset that you need to be comfortable and pack smartly. I don’t know the cities you’re planning to visit but if you’re by the coast at all you’ll want your bathing suit and a pair of shorts or maybe a skort. I’d leave the dressy gold heels home and take your DV taupe braided sandals. They go with everything! Just my $0.02 of course.

    Sometimes those travel blogs are over-focused on preventing theft (you end up so scared and have all your belongings locked up in your undies) and they urge you to buy/wear certain travel comfort clothes and plan to wash your clothes in the sink….I’ve never washed clothes on a vacation). You know what I mean?

    Side note: You can definitely pull off the comfort sandals look! You have great feet and legs; they all look cute on you!

    1. You’re funny. I hear ya on the crinkle dress. I think it’s one of those you have to see in person. If it wasn’t so pricey, I might reconsider, but I feel so sure about that blue one, for example, that I don’t want to keep one that I’m wishy-washy about.

  15. Hi!
    Can I ask what size you tried on in the Evereve Maia dress?
    We will be in Italy June 18th – July 2nd and I love these ideas! Rome, Sienna and Florence this trip.
    Thank you!

  16. I’ve been to Italy 5 times at different times of the year. We went once in September and it was HOT. I don’t recommend black for walking around in the Italian summer sun – the sun just beats down on you. Also heels are tough on the cobblestone streets and you will do a lot of walking. Flats or low wedge, sneaker or comfy sandal. I didn’t see women wearing heels in the summer. Have a great time!

  17. Enjoyed this post. Love to wear dresses but it is challenging to find the ones that hit on all cylinders
    such as color, length, and fit. The tiered look with a lot of flowy fabric that seem to be everywhere is not my fabric. Trying to find a well made column tee shirt/tank dress but not having any luck

    sharing what you order and like/don’t like.

  18. I have to agree with the others; leave the heels and the fancy dress home. Or, let me put it this way, when you run out of space in your carry on luggage those items should be the first to go.

  19. The short dresses look cute on you. I can’t find dresses I like on me anymore. When I was young I had a lot of dresses now it’s just a total of 8. For me that’s not much ☺️.

    Just out of curiosity what are you going to do about laundry since you want to have only a carry-on? Hotel laundry is expensive. I couldn’t do it. I’m looking forward to hearing all about it when you come back.

  20. I love a comfy dress for the type of vacation you will be taking, and you have some good contenders here. Have you also considered skirts and tops? You could wear the same skirt multiple days and just change out the top.

    We never change for dinner on vacation. We’re rarely near our hotel at dinner time, so we just go as is. Unless it’s really important to you to have a fine meal in a place that would require nicer clothes, I wouldn’t take special clothes for one meal.

  21. I think you hit right on the money with your keepers! I loved that pink dress when you first brought it to my attention, but seeing it here on you makes me rethink it. It’s a lovely dress, and it looks nice on you. But I’m also not loving the trim and sleeve length. I guess I gotta keep looking. My green pocket t-shirt dress and white denim jacket that I ordered from Gap Factory after your post the other day arrived yesterday and I’m very happy with them! My J.Crew cashmere socks order was stolen off the UPS truck yesterday. I was so sad. J.Crew customer service was wonderful and is overnighting me a new order. I had to learn today to give myself a shot for my migraines. Afterward, I treated myself to the Amazon clutch you’ve been carrying. ❤️

    1. I can’t believe your package was stolen off the truck! That’s nuts. Glad to hear their customer service is good, tho. And my goodness… a shot for migraines? Yours must be extreme. I hope it helps, at least.

  22. Have you tried the Reverie dress by Z Supply? The shirttail hemline makes it look a bit casual but the v-neck and the slightly higher cut of the shoulders would be perfect on you.

  23. You look phenomenal in both the blue and black short dresses especially the blue! They are perfect for a night time dinner on a sultry summer night! They also would be great for nice dinners along the coast and you can also use them for other trips that are beach locations.

  24. Somewhere(and I have been looking) you shared a pink shiny dress with puffy sleeves to the elbow. V neck . Knee length. Can you find it for me? Thank you!

  25. The black shorter “athletic” dresses all look great in you. I personally prefer skirts over dresses when I travel – that way if it somehow becomes cool or rainy I can swap in pants for the skirts. I do usually pack a dress or two, it’s just that the skirts are the workhorse

  26. I am going comment twice because I keep getting kicked off the website.
    We were in Italy in July and it’s hot!!! I brought a lightweight short sleeve sweater to wear in churches, especially the Vatican. THe guys need pants.

    1. Also,I don’t necessarily agree with the others about changing clothes for dinner. We found it was so hot that even if it didn’t seem like we weee using our time we’ll, we got up very early and got out to sightsee while it was cooler in the morning, ate lunch and then went back to the hotel to cool off and rest. I usually changed for dinner – you can rewear your dinner dresses! We used our rest time to plan the next day, research restaurants etc. if we tried to keep going, we were so hot and cranky, it wasn’t worth it.

      1. Yes, that is how we tend to travel too. I will go through our itinerary, but I’m pretty sure we have a few afternoons without tours or specific plans, and I expect I’ll want to lay down for an hour in the hotel before going out to dinner. I would likely change after that. Don’t they tend to eat late too? It’s interesting to read everyone’s travel habits and preferences. I will need to really consider our travel style as I decide how I want to pack.

  27. I just ordered the black and white twist tie front that you suggested. It’s just my style. Thank you for sharing it. It wasn’t 40% off, but that’s okay. It’s my splurge for myself, and I know it will be something I can wear many times over the years to come. I’m not going to Italy, but I am going to Savannah this summer. It will be great for going out to dinner.

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