Try On Haul: Denim, Fall Dresses, Cocktail Attire + More

I’ll just put it right out there — this post is a doozie. And it is all over the map . . . jeans, cocktail attire, fall dresses, and about 25 retailers represented.

Okay, I exaggerate. But still. It’s a lot, so I’m just going to dive right in.

Try On Haul: Denim, Fall Dresses, Cocktail Attire + More

The usual disclaimers apply — I’m 5’5″ with a slightly hourglass shape, and I usually wear small tops and a 6 or 8 in pants. My average dress size is an 8, but depending on the brand, I have everything in my closet from 4 to 12.

Links and descriptions are below the pictures, but I’ve split up my commentary a bit this time because I have so many pictures and so many thoughts about each piece.

Try On Haul: Denim Comparison

I’ve been experimenting with a bunch of different crop straight jeans, and I’ve tried them on with various shoe and top combinations, trying to figure out how to wear this new silhouette.

I’m learning that getting the length right is key to making this look work. I like mine to be a good inch or two above the ankle bone for a true crop. The ankle-length ones just look like floods — at least on me.

First up, a true crop straight . . .

GAP High Rise Cheeky Straight Jeans size 29 // These are a true crop straight jean. They look a lot like the Levi’s that have made this look so popular, right down to the thicker vintage-inspired denim and the lighter wash.

Believe it or not, I actually like these. I got a mixed response when I posted a picture to Instagram, but I think they’re fairly flattering, all things considered. I mean, I still think I look best in skinnies, but these are fun for a change.

I styled them two ways, trying to figure out if I wanted to commit. This first way is a fall look with a shorter sweater and loafer mules.

And then for summer, with a tank top and leather sneakers.

Notice how there’s a good two inches of skin showing between the hem of the jeans and the shoes. Since our ankles tend to be the thinnest part of our leg, it’s flattering to expose some skin when wearing a cropped pant.

I like the distressed hem on the back, and I also like the smaller rear pockets. In fact, the pocket placement in general is very flattering.

Also, these jeans are verrrry comfortable. Well done, Gap! I’m impressed.

THE VERDICT: I kept them, but I’m not sure how much I’ll actually wear them. My 16-year-old is horrified that I’m wearing them and reminded me that my tagline says, “Friends don’t let friends wear mom jeans.”

I’m not sure I’d qualify these as mom jeans, though. They don’t give me the long butt (haha!), and the rise isn’t super high. I’m definitely going to keep experimenting with them.

FYI, these jeans also come in tall and petite sizes.

GAP High Rise Cigarette Jeans size 29 // I also ordered these cigarette jeans from Gap, wanting to compare them to the AG Prima that I like so much.

YOU MIGHT ALSO LIKE: What Are Cigarette Jeans? {and Why I’m Embracing Them This Fall}

I’m not crazy about these. While they aren’t necessarily unflattering, they’re a little longer than I like, and the wash looks cheap to me. I can’t explain why, exactly, I just don’t like it.

The fit is okay, although I think they look better cuffed. See below.

THE VERDICT: I returned these because I have others I like better, but if you’re looking for a pair of cigarette leg jeans in this price range, these are a decent option.

They also come in tall and petite sizes.

MOTHER Rascal Ankle Snippet Jeans size 29 // I really like how these fit and feel, except they’re ankle jeans, and I prefer my straight leg jeans to be an inch or two shorter.

Unfortunately I can’t cut them or cuff them because they have a split hem, and I wouldn’t want to lose that detail.

According to the website, these have a 26.75″ inseam, but I’m not sure about that. They seem longer to me.

I wish I’d measured and compared these to the Gap pairs above, but Shopbop has a 15-day return policy, so I sent them back ASAP when I knew I wasn’t going to keep them.

It’s too bad because they are soooo soft and comfy, I like the rear pocket placement, and the wash is great too.

I also tried them with ankle boots, to see if I liked the length better with a different shoe, but they just meet the top of the bootie, which is awkward.

They should expose about an inch of skin, or they should cover the top of the bootie without getting caught on them.

I gave them one more try with these peep-toe booties, and they did the same thing.

What I should have tried is a pair of sock booties with a higher shaft so the jeans can be worn over-top, but mine are currently packed away.

THE VERDICT: As I said, I returned these, but I might revisit this style when fall is in full swing and I have more booties to experiment with.

AG Prima Ankle Skinny Jeans size 29 // For comparison sake, I took a few pictures in my AG Prima cigarette jeans. These are called skinny, but they have a 12″ leg opening, making them more of a slim straight.

They are ankle-length, so I usually wear them cuffed to give them more of a cropped silhouette.

Here’s how they look worn un-cuffed with the same shoes.

This works okay with loafers, but not so much with booties. I always cuff them with booties.

THE VERDICT: I own and love these. Highly recommend!!! I did get them on sale for $149 during the #NSale, so I don’t really recommend paying full price, but I’ll let you know if I see them discounted again.

Kut from the Kloth Cigarette Jeans size 6// For a more budget-friendly option, these cigarette jeans by Kut from the Kloth are a nice fit. They’re a couple inches shorter than the AG Prima, so cuffing isn’t necessary for most of my shoes, but I do like to give them a small cuff with booties.

THE VERDICT: These are a great pair of budget-friendly slim straight crop jeans. You can tell that the whiskering and distressing details aren’t as natural looking as the higher priced jeans, but for the price, these are great.

These are currently on sale for $53.70, and they come in petite sizes!

AG The Prima Raw Hem Crop Jeans size 29 // When I saw these AG Prima crops, I knew I had to try them, since I’m always cuffing my ankle-length Primas. These have a 26″ inseam and a 12″ leg opening with a split hem.

I really like the darker wash for another option, and the shorter 26″ inseam is perfect with mules.

I think they’re a little too short with these sandals, though. It’s an awkward amount of skin showing.

But they seem to look okay with these booties, which are only a half inch taller in the shaft than the sandals. I dunno, what say you??? #fashionishard

Also, does anyone else find it curious that the Mother Rascal jeans (above) with a 26.75″ inseam were too long with these booties, and these have a 26″ inseam, and they’re almost too short? I can’t believe those measurements are both accurate. I wish I still had the Mother jeans to measure.

THE VERDICT: I’m undecided on these. Since I got them at Nordstrom and their return policy is so generous, I’m going to keep the tags on and hold onto them for a while until I have more opportunities to style them with different shoes and tops.

Ann Taylor Sculpting Pockets High Rise Straight Leg Jeans size 6 // These jeans have a 27 1/2″ inseam so they’re definitely ankle length.

Again, maybe my eye just needs to adjust, but I’m not crazy about this length in a straight fit. They also seem to flare slightly at the hem, giving them more of a kick flare silhouette.

They are comfortable, though, and I like the black wash for a change.

I tried them with a these sandals to see if I like them better with a heel, and I do. I’m not quite sure what it is about this combo that works, but I think it does.

THE VERDICT: I did return these, but I might revisit them later in the season. I think they’re a good option for those looking to update their silhouette.

They’re 40% off with code LASTHURRAH.

also wearing: Kasper snake print blouse

Ann Taylor Sculpting Pockets High Rise Skinny Jeans size 6 // These are great for classic black skinnies, especially if you like a higher rise. They have a 11″ rise with a 29″ inseam, and they’re very flattering.

THE VERDICT: I returned these because I don’t need them, but if you are looking for high rise black skinnies, they’re worth a try, especially at the sale price!

They’re also 40% off with code LASTHURRAH.

also wearing: Kasper snake print blouse and Sam Edelman Laurna mules

Okay, let’s move on to dresses!

Try On Haul: Fall Dresses

Ann Taylor Polka Dot Wrap Dress size 4 // This dress is giving me all the Pretty Woman vibes. I love the rust color, and the polkadots are fun.

I had to size down to a 4 in a similar AT dress a couple months ago, so I ordered both the 4 and 6 to try. The 4 fit well everywhere, except it pulled just a bit in the chest.

(Pictures of the size 4 are above. See the size 6 below.)

Ann Taylor Polka Dot Wrap Dress size 6 // When I put on the 6 and tried to snap it, I was surprised that it barely closed. Then I realized the snap was located in a different place — it had been moved over an inch or two from its original location. Can you see that?

I think someone moved the snap, probably wore it, and then returned it. Isn’t that crazy!?!

THE VERDICT: Both of these went back, but I’d like to try a size 6 that hasn’t been tampered with. It’s a gorgeous dress. In fact, I just ordered it.

And it’s also on sale for $66.99!!!

Ann Taylor Terra Floral Smocked Flare Dress size 6 // This is a nice dress for fall, and I like the print a lot. I feel like it’s flattering and would be great for work, church, or date night — depending on your footwear.

I think it would be smashing with rounded toe suede pumps for work, and I like the strappy sandals for date night. You could also do a black bootie.

THE VERDICT: I sent it back because I don’t really need it right now. If I was doing 25 Days of Fall Fashion, I would have featured it for sure.

This dress is currently 40% off with code LASTHURRAH.

Vince Camuto Highland Printed Midi Dress size 8 // I wanted to love this leopard print dress, but it just doesn’t flatter me. It looks like I have no waist, but I think it would be gorgeous on the pear-shaped gals out there! It runs TTS; the 8 fit me perfectly.

VERDICT: Returned, but I think it’s a great dress. Just not for me.

also wearing: Sam Edelman Yaro sandals

Try On Haul: Fall Wedding Guest / Cocktail Dresses

I’m still on the hunt for the dress for this black tie optional wedding I have coming up. I loved all of your input on this post, and it really helped me hone in on what I want for this event.

First, let’s recap.

Xscape Mesh Inset & Embroidered Evening Dress size 8 // This was my favorite dress of the lot, but I think I’ll be more comfortable with a knee-length dress as long as its formal enough.

Eliza J Sequined Sheath size 8 // While I love this navy dress from last year, I feel it’s too short and glitzy for a wedding — especially one where the ceremony is held in a church. It’s more of a holiday party dress, so I’m going to hold onto it and hope I get to wear it later this year.

Eliza J sequined cap sleeve shift dress size 8 // Likewise with this taupe shift. I love it, and it fits like it was custom made for me, but I feel like it’s more appropriate for New Year’s Eve or a wedding in Vegas.

I decided I want something knee-length and not so sparkly — but as elegant and as formal as it can get without being a floor-length gown.

Aqua Scuba-Crepe Dress size 8 // I had high hopes for this scuba crepe sheath, but it was a total bust — pardon the pun. It was so revealing, I couldn’t even take pictures to show you. The fit is just really off for me.

Eliza J Cowl Back Ruched Stretch Sheath Dress size 10 // This one is closer to what I want. I like the length, the fit, and the ruching details, and the cowl back is dramatic and fun.

But it’s not very flattering from the back, and it’s hard to move in. I think that would be annoying over the course of the evening.

THE VERDICT: I sent this one back. If you like it and are considering placing an order, size up. The 10 barely fit, and I am typically an 8 in Eliza J.

Aidan Mattox Women’s Floral Printed Jacquard High-Low Gown size 8 // I first saw this dress on Bloomingdale’s, but it was sold out in my size so I tracked it down on Amazon.

THE VERDICT: I returned it. I don’t want to stand out THIS much at my nephew’s wedding. But if you have an appropriate event, I think  it’s really fun.

Eliza J Ruffled One-Shoulder Dress size 8 // This dress has potential. For one thing, I love the navy scuba fabric. It’s super thick and luxe and very forgiving for a sheath.

The length is perfect for a more formal event, and the ruffle shoulder detail is gorgeous, but I just don’t want to deal with a strapless bra if I don’t have to.

THE VERDICT: While this one could work, I decided to return it on account of the bra issue. And because . . .

I found this . . .

*cue angels singing*

Eliza J Side Drape Laguna Crepe Cocktail Dress size 10 // I knew Eliza J would come through for me if I looked hard enough! She always does, even if I did have to size up to a 10.

This dress is exactly what I wanted — the length and material are understated and elegant, the v-back adds some extra pizzazz, and the bow detail is just the right amount of drama to set it apart.

Best of all, it fits perfectly without the need for any alterations.

THE VERDICT: Keeping, duh!!! Now I just have to figure out my shoes and accessories, but that’s the fun part!

I’m thinking of having my hair put up. I usually curl it for dressy events, but I feel like this dress requires something more sophisticated than my loose curls.

I do hate to go to the trouble of making a salon appointment, though. I guess I could wear it straight and get a sequined clip for the side. What do you think?

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54 Responses

  1. Hate to say it but I have to agree with your daughter about the mom jeans.  I think you’re right about the rise and back pockets,  but I think it’s a combination of a vintage/90s type wash with a baggier leg style.  I think straight leg jeans can easily give off a mom jean vibe, more so than skinny or the cigarette trend.  The wash probably makes a big difference when they’re in that gray area.   
    Really like that navy dress with the ruffled one shoulder neckline,  but I’m with you on not having to wear a strapless bra!  Especially if you’re going to be dancing!  Think you definitely picked a winner in the blank dress! 

  2. I too, agree with your daughter on the mom jeans. Not liking either Gap jeans or the AT jeans. The skinny AT isn’t bad but no to high waist.  The Prima ankle gorgeous and I like the mild distressing on the Kuts. Loved the ruffle shoulder scuba but I get the bra issue. Your Eliza J black is stunning. My friend had a peachy pink long version of that as a MOB in spring. She was stunning.  The short version has a slightly different vibe but it is incredibly elegant on you. Totally agree with your choice. I’m still loving last season’s holiday dress but agree on church issue. Hope you get to wear it this season. Eliza J is also my bud when searching out a great dress.  As for Pretty Woman dress, I’m tired of seeing it all over the place in tops and dresses. It strikes me a bit lame – but that just my opinion.  The snap moving is bad news, shame on someone. Great post. 

  3. Thanks for the heads up about the Nordstrom Sale. I discovered it yesterday, however, and immediately checked my wish list and ordered 4 things from it that were on sale and in my size, including the Kut from the cloth cigarette jeans and the Kut crops that you’be been wearing all summer!  Yay!  I am still waiting thinking of ordering a few other things. Love your black dress for the wedding!

  4. Love that polka dotted dress! So fun and love the color! And I think it looks fantastic on you!
    Thanks for doing these try-on posts, I really enjoy them!

  5. Wow I guess the bum and length of our jeans can make it or break it as far as keeping them.. you’ve been giving me and keep giving things to consider before making the purchase. I’m 5’3 so I don’t really care for jeans that hide my ankles and try to get the right length just sitting above the ankle like you’ve mentioned. I’m still not sold on the Gap crop for some reason but your the professional:) I absolutely LOVE the dress you’ve chosen for the wedding and you’ll look great no matter how you style your hair but the clip idea sounds nice without being over the top.
    Have a great day😀

  6. I like the Gap (cheeky straight) jeans on you. They are flattering and skim right over your body — they are loose without looking baggy. It’s nice to have a variety of jean styles, you don’t always want to have tight jeans.

  7. I think you will be beautiful in the black dress, no matter how you choose to wear your hair. I do think it is so pretty straight, and adding the clip would take it up a notch.

  8. I also agree with your daughter that that first pair of jeans have that undesired “Mom jeans” look. Its the color/wash and style. Your pick of cocktail dress for the wedding is gorgeous!😍 The dark wash AG jeans are so flattering.
    Fall is definitely upon us. I was surprised that Starbucks is already selling pumpkin spice lattes as of August 27th….. Is it just me or are retailers really jumping the gun on seasons? When I saw kids’ snow suits at Costco in July, I had to roll my eyes “c’mon”……..

  9. I’ll have to come back to look at the jeans some more, but I love your dress pick! Yes, it’s so nice when a dress just seems like it was designed with you in mind. The neckline is super flattering along the the perfect silhouette! You’ll have this lbd for years! Now you get go for fab accessories–I’d do a really stand out necklace, but if you wear your hair up, I’d switch to larger earrings…however the dress seems to be crying out for some bling (but you know this of course!) Maybe a blow out with curls/waves so it will stay all weekend? 

  10. I agree with your daughter too – the bagginess in the thighs of those jeans doesn’t do anything for you. 

  11. Love the black dress,,,
    Did it run way small ..since you ordered 
    up two sizes?
    Thinking of it for future event.

  12. Those Gap jeans look great on you – they don’t look like mom jeans! Thank you for all the information you give us about how jeans fit: pocket placement, length, how to wear them with different types of shoe, etc. It has been most helpful to me when trying to figure out why my jeans just don’t seem quite right.
    Love the black dress you found for the wedding – very flattering!

  13. That last black dress looks great. I can see why it was the winner. The long black one looked good on you too (more formal though). I used to have cigarette jeans from Lucky that I LOVED, but they don’t fit any more and I’m sad.

  14. Love, love, love those Cheeky Straight Jeans on you (!!) and I can’t wait to see if Nordstrom might carry them. (I hate the shipping return process from other stores and we have a Nordstrom rack in my neck of the woods so Nordstrom is my To-Go store!) Also wanted to give you a knuckle-bump on the dress you chose for the upcoming wedding – Just Perfect!!!!

    1. They’re Gap so Nordstrom won’t have them, but Gap offers free shipping on orders over $50 and free returns for 45 days. They’re one of the easier retailers to shop online.

  15. Great and fun try on haul – love the dress for the family wedding. Yes dramatic hair for a dramatic dress – but soft!!
    Thanks for all the looks.

  16. Oh my – your dress choice is fabulous! I have noticed that clips are back too. Thank you so much for all the photos and descriptions and the whys and why-nots. It is so helpful. I also have to give you a shout out for showing your backside. It really helps to see the fit across shoulders and waist and the pockets (jeans and shorts). I have pared down my fashion blogger following for that very reason – they never show the rearview!

  17. You are so brave showing all the clothes that don’t work! Makes me really appreciate all the hard work you put in to show us trends and styles that work. Absolutely love the dress you picked out for the wedding. The other short dresses were adorable but agree not for a church wedding. You have gorgeous hair so putting it in a pony tail with a pretty clip would work for you! And yes PLEASE keep us updated on a sale for the AG jeans.

  18. I was a skeptic since I like the sequin dress so much, but yes, the black one is it! I love the bow/not bow detail, so fun and yet elegant. You look gorgeous and can wear that all night without anything bulging or rolling.
    Good work!

  19. How high is the rise on the Gap jeans? The web-site doesn’t say and I know from experience that anything higher than 9 3/4″ looks terrible (and feels terrible) on me.

  20. The black side drape cocktail dress is perfect! It’s so pretty on you. It’s covered up enough for church, but not a bit dowdy. I think a sleek, simple hairstyle is best with that dress.

    When it comes to jeans, I’m having challenges, because I still like mid-rise. High waist jeans feel uncomfortable to me. And they don’t seem to suit my boyish figure (wide waist, narrow hips). I’m glad you reminded us about Gap jeans. I need to revisit them.

  21. I think I like cropped straights better when they are cuffed because they look intentional. Otherwise it just looks like you have a growth spurt.  

  22. Wow – great post. I said it before and will say it again – I like those gap jeans on you! They are not “mom jeans” (no high waisted pleats or baggy hips/tapered legs). And I think the wash is flattering. I agree with you about the lengths (shorter being better and making them less clunky looking). Doesn’t mean you ditch the skinnies, but it’s a nice alternative. Your choice for the wedding is lovely. I loved that silvery cowl dress until you showed the back – reminds me to look at all angles of something! Anyway, I’d wear your hair up with a fancy clip of some sort with some nice statement earrings. I find “up hair” more elegant for black tie (if your hair is longer). I know this is “optional”, but to me, all that means is that a man is not required to wear a tux. I hear you on not wanting a floor length gown, but I’d go all out with the rest of your look.

  23. The dress your keeping is gorgeous!! I think curling your hair and putting in a jeweled clip would elevate the look. I can’t wait to see the pictures when your ready to go… Your a beautiful person inside and out. You don’t know how much you have personally helped me!!
    I love the try on haul!! 🥰


  24. Oh my goodness you look beautiful in the last blue dress!! You made the correct decision! You look so wonderful!!! Now you can relax and enjoy the wedding!

  25. I just looked at the dress on line and it says it comes in pink and black. So the dress I thought was blue May in fact be black. I still love it on you!!!

  26. The black short dress is beautiful. I would wear your hair up. It would be elegant and go with the feel of the dress more. Also love the navy one shoulder dress. I agree with your daughter. These baggie shorter jean styles just feel frumpy to me. Especially the lighter “Mom” washes. 

    1. Wearing your hair up would allow for some nice statement earings and a bracelet. Then the dress could just speak for itself. No necklace. Kind of Audrey Hepburn style. Can’t wait to see what you decide though. You always look amazing!

  27. Love the black dress you picked out—LOVE! It could not be more perfect. I also really like that leopard dress on you (not for the wedding, of course), and think it looks really good at least in these pictures.

  28. I really like these posts!  I ordered the Kut jeans.  I had tried the AG, but the rise is wrong for me.  Fingers crossed for these!
    Your dress looks gorgeous and so glad you found one.  I need to find a semi formal for my son’s wedding in October.  I need a petite so it makes it even harder.  I’ve bought and returned 4-6 so far.  
    Thanks for the inspiration!

  29. Love the black dress, it’s stunning. And I actually like the leopard print dress on you; it looks very flattering!

  30. Yes to your dress! Lol. I do love the one you chose best. Beautiful and flattering and  does seem perfect for your occasion. It’s nice to know I’m not the only one who struggles to find the right dress for these events. It seems to take forever and feels
    ridiculous when I’m just a guest, not the mother of the bride/groom! But your effort paid off! 

  31. Love, love the dress you kept for the wedding. I can’t wait to see what shoes you choose and how you accessorize it. 

  32. I love this post so much! Definitely that last dress is my favorite too! Go for the updo for fun!! I am thinking about it also for the fall wedding I’m going to! I think it would be fun to show some options your hairdresser might come up with! Can’t wait to see your accessories and shoe choices! 

  33. I’m 5’2”, and I bought a pair of the AG Prima cigarette ankle jeans in 5 year blue essence (they do not have the side slits like yours). They will have to be hemmed. What length do you think it would be best to hem them to? (I will wear them with flats, loafers, and booties.) Just above the ankle bone or higher than that?

    1. Mine don’t have split sides either. 🙂 It’s such a personal choice, depending on your body type and proportions, I really can’t say for sure. I think you need to try them with different pants (and the tops you will wear with them too) and experiment. Take pictures and compare pictures. It’s easier to tell what looks best from pictures, for some reason. I hope that helps!

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