Fall Fashion Try-On Haul for Women Over 40

SIZING NOTES: I’m 5’5″ and I usually wear a small or medium in tops and dresses, a 29 or 8 in jeans and pants, and a size 8 shoe. Unless otherwise noted, items below run true to size.

Jenni Kayne Everyday Sweater

at Jenni Kayne (S) // similar FRAME jeans (29) // similar mules // earrings

I’ve had this sweater for awhile; I got it when it was on sale over Memorial Day or the 4th of July, I can’t remember which. I love my Jenni Kayne cashmere fisherman sweaters, and this one has such pretty details, so I wanted to try it.

The fabric is 40% wool, 25% viscose, 25% polyamide, 10% cashmere. Because it isn’t 100% cashmere, the price isn’t quite as daunting as a lot of their sweaters. It’s not quite as soft either, but it still feels nice, and it’s a good quality.

I love the relaxed fit, rolled edges, and contrasting ribbed cuffs and hem.

VERDICT: This one’s a keeper! If you like it, I’d recommending waiting for a sale (Labor Day, maybe?) or using the 15% off coupon for registering your email address.

J. Crew Midi Denim Skirt

at J. Crew (29) // sweater vest (S) // similar sandals // earrings

I hesitate to even share this skirt because it’s almost sold out, but it’s a good one, so if you can snag one in your size, go for it! It’s 100% cotton, so more of a rigid denim, and I like the subtle acid wash vibe going on.

This skirt runs big; size down one full size, if ordering. I’m wearing the 29, and I re-ordered the 28 before it sold out.

Here’s how it looks with a sweater tucked in, but I prefer the black cable vest, above. I feel like I look more balanced with the top over the waistband, but that requires the top to be the exact right length.

According to the website, the black sweater vest is 20 1/2″, and it also looks perfect with wide leg jeans, so I’m going to make a mental note of that.

Pro Tip: Knowing your ideal measurements for various garments makes online shopping much easier! I can often tell before ordering whether or not an item will fit, based on the measurements.

VERDICT: Keeping the skirt in the size 28, assuming I like the fit.

I also ordered these sneakers. I love how they resemble the Adidas soccer sneakers that are all the rage right now, but they’re not exact.

PAIGE Leenah High Waist Ankle Wide Leg Jeans

at Nordstrom (29) // sweater (S) // similar sandals // earrings

Speaking of high rise jeans and knowing your measurements, let’s discuss these jeans! They’re an #NSale purchase, so you’ve seen them before, but they’re back in stock in a few sizes, and I have a feeling I’m going to be wearing them a lot this fall and winter.

Last year around Labor Day, a bunch of #NSale items went back on sale. Since these are a Nordstrom-exclusive style, I have a feeling these might be included if that happens again, so keep an eye on them!

For some reason, the measurements aren’t posted online, so I measured mine. These jeans have an 11″ rise and a 28″ inseam with a 20″ leg opening.

The faded medium indigo wash has some mild distressing for a relaxed, vintage appeal; and I love the trouser-inspired released hems.

Because of the volume on the bottom and the length, I prefer these jeans with heels, but they can work with flats. I tried them on real quick with slide sandals yesterday, and they don’t look as bad as I’d anticipated.

I think it’s because they are cut just close enough to the thigh as to not look too voluminous, and then the leg is more of a straight wide leg style than a flared wide leg style, if that makes sense.

It also helps to wear a shorter, more fitted top. This Gap Factory sweater tank is perfect.

Here’s how these jeans look with ankle boots; I love this look for when the weather cools down.

Both the boots and the funnel neck cashmere sweater were #NSale purchases, so I got them for 40% off. Keep an eye on them, as they may go on sale again sometime soon.

VERDICT: I’m keeping these jeans, and I also kept those boots, but I did not keep that funnel neck sweater; it’s thinner than I like, and I don’t like how the funnel neck lays on me.

Avec Les Filles Swing Barn Coat

at Nordstrom (S) // Paige Leenah (29) // Blondo booties (8)

This was also an #NSale purchase, but I didn’t get around to trying it on until just a couple weeks ago. It’s a nice mid-length, and pretty flattering overall. I like the silver hardware, too.

VERDICT: I returned this because it’s too small and the color is warmer than I prefer, but it’s a nice quality coat. Size up, if in between.

Evereve Georgina Cardigan

at Evereve (S) // PAIGE Leenah (29) // Aquatalia booties (8)

This sweater is an Evereve find. I love the design in the knit, the seasonal olive color, the 21″ length, and the relaxed but not oversized fit.

I also appreciate the modest v-neck so it can be worn buttoned-up, as shown here. I just wish it didn’t have drop shoulders, as they always seem to make my already boxy shoulders look even broader.

Here’s how it looks with darker wash jeans and black boots. These are the MOTHER Hustler ankle bootcut jeans with black Franco Sarto booties. I like both looks equally. It’s good to have options!

VERDICT: Undecided. The drop shoulder might be a deal breaker, which is unfortunate because it’s practically perfect in every {other} way!

Farhety Sunwashed Long Sleeve Polo

at Faherty (S) // MOTHER denim (30) // P448 John sneakers

This rugby shirt has such 90s vibes… I feel like I’m back in college wearing this! Except back then, I would have been wearing tapered Gap jeans and duck boots, haha!

I love the colors, especially paired with light wash denim. But I also know me, and this look is just too sporty for my taste. The old me would have kept it, thinking there will be times when I want to look more sporty, and it’s cute, and I like it.

But then I thought about what I reach for when I want to look more “sporty” and this isn’t it. I’m always going to opt for a raglan tee or thermal, or a beyond-basic sweatshirt. The rugby shirt just isn’t me.

VERDICT: As much as I like it, I know I won’t reach for it, so I sent this back.

MOTHER The Dazzler Ripped Mid Rise Ankle Slim Jeans

at Nordstrom (30) // Faherty top (S) // P448 John sneakers (39)

I’ve showed these jeans before, but in case you missed it, they’re another #NSale find. These were also exclusive to the #NSale this year, so I predict they may go back on sale at some point in the not too distant future.

They’re a slim, straight ankle jean in a light wash with subtle distressing and one ripped knee. I sized up to a 30 because they didn’t have the 29 in my store, and they’re really comfortable. I would still say they’re true to size; I’m just not staying true to my size right now, haha!

Finn Striped Sweatshirt

at Evereve (S) // MOTHER denim (29) // P448 John sneakers (39)

This is what I would call an “elevated sweatshirt”, and stripes are a big trend right now. I like how they use a color blocking technique with a different scale of stripe on the sleeves. I hear color blocking and mixed pattern designs are on their way back.

While it’s cute, the drop shoulder, and the way it fits loose on top and snug in the waist makes me look a little top heavy, and I didn’t find it comfortable.

VERDICT: I returned it, but it’s a cute top and good quality. If you like it, it’s worth a try!

Cloth & Stone Curved Hem Shirt Dress

at Evereve (S) // similar slides

This dress is cute, and the fabric is lightweight and soft and comfortable, but it’s a little too snug, and the belt doesn’t hit me at the right place on my body. I need it to be higher, I think. Belted dresses like this are hard for me to wear because I’m so short-waisted.

VERDICT: Returned it.

Michael Stars Solana Midi Dress

at Evereve (M) // Aquatalia booties (8) // Vince wedges (8) // earrings

I shared this in my last try-on haul, and it came tied right in the middle of the body, so that’s how I tried it on, and it never occurred to me to tie it to the side. D’oh. That’s how my mind works. I’m not one to think outside of the box or see other options.

When you all told me it’s really cute and flattering tied to the side, I decided to give it another shot, and that makes all the difference.

Ribbed dresses are trending, and this one seems to be fairly forgiving, in that it doesn’t over-accentuate the lumps and bumps but still has a body-con silhouette. The color is also really nice for transition season, and the fabric is good quality.

VERDICT: I decided to keep this dress!

Ribbed Midi Sweater Skirt

at LOFT (M) // tank (M) // cardigan (M) // earrings

You may remember this cardigan and sweater tank from my last try-on haul. I decided to order the skirt to make a monochromatic outfit, and while I like the look, I’m not a fan of this skirt.

This goes to show how different ribbed fabric can be. The Michael Stars dress (above) is quite forgiving, but this LOFT skirt… not so much.

It clings to every lump and bump, and it over-emphasizes the discrepancy between the width of my hips and my legs. The Michael Stars dress still fits close to the body, but it isn’t so tight against the legs, and it doesn’t seem to be quite so clingy. Also, the waistband on the skirt is uncomfortably tight.

VERDICT: I could possibly size up to a large, but I just sent it back. If you decide to order, definitely size up at least one size.

PAIGE Sasha in Stefania Distressed

at Saks (29) // at Nordstrom (29) // at Anthro (29) // sweater (M) // wedge sandals (8)

I bought these jeans on the Saks spend more, save more promo they had going on last week. This week you can use code SUNNY23SF to save up to $200 off your Saks order, which makes these jeans $50 off.

I was expecting more of a straight leg silhouette, but they seem closer to a wide leg to me. Each website labels them differently, which tells me that I’m not alone in my confusion.

This is from paige.com: Sasha is our new high-rise straight leg with a loose, relaxed column fit. This pair is cut from our PAIGE VINTAGE denim in light wash with lived-in details, an extended coin pocket, and a 32” inseam. But Nordstrom and Saks list them as wide leg jeans, so make of that what you will!

Here are the facts: These jeans have an 11 3/4” rise, 32″ inseam, and 21″ leg opening. (Also, the black wash is available in 32″ and 34 1/2″ inseams, so that’s a great option for the taller ladies among us.)

Whatever you want to call them, I’m kinda digging these jeans. They’re soft and stretchy, and I like the straighter wide leg silhouette quite a lot in a full-length style. It seems more sophisticated and a little more under understated than, say, the MOTHER Roller (10″ rise, 31″ inseam, 26″ leg opening) that I’m wearing below.

VERDICT: I think the PAIGE Sasha is a keeper!

Cashmere V-Neck Sweater Vest

at J.Crew (M) // PAIGE denim (29) // PAIGE wedge sandals (8) // earrings

This sweater is that “magical” 20″ length for wearing with higher rise jeans, but for some reason it looks a lot shorter than the black cable vest and olive cardigan.

I sized up to a medium to get a looser fit, but it still looks awkwardly small, and the v-neckline is way too low for my comfort level.

VERDICT: Unfortunately, this went back.

J.Crew Cashmere Cropped V-Neck Sweater

at J.Crew (M) // similar MOTHER Rollers (29) // Aquatalia booties (8)

I was wondering if I want to have some shorter long-sleeve sweaters to wear with wide leg jeans this fall and winter, so I also wanted to try this cashmere shrunken V-neck.

This seems like it would be a long-sleeve version of the sweater vest above, but it’s actually not as low-cut, which is nice.

I just can’t decide if I like the cropped length in a classic style of sweater like this. It definitely works in the vest (above), but this looks a bit off to me.

I also feel like it’s intended to fit looser, as shown on the model, but I already sized up to a medium, so I’m just not sure this sweater is for me.

These jeans only have a 10″ rise, so I decided to try the sweater with these Pistola utility trousers with a 11″ rise…

Pistola Pamela Trouser

at Evereve (29) // sweater (M) // clogs in Taupe (8)

This looks a little better, but I’m still not sure I love the sweater. I do, however, like these pants!

I wasn’t sure about this silhouette, but something about the way they taper, and that perfect 27 1/2″ ankle length seems to work. They’re a comfortable 98% cotton, 2% spandex stretch twill, and I always like to have a pair of olive pants in my fall closet.

I was wondering if they were too big, but I think this is how they’re supposed to fit. They aren’t too big in the waist, which is where pants tend to be too small for me.

My 17-y/o daughter came home from school when I was doing this try-on, so I asked her what she thought, and she said she likes them, so that’s always a win in my book!

VERDICT: Keeping for now, I want to try them with some other tops.

Rebecca Minkoff Zip Around Croissant Hobo

at Saks (on sale) // pants (29) // tee (M) // clogs in Brown (8)

I believe I mentioned in my 2023 handbag trends post that I was ordering a few brown bags to try out and compare. They were also part of the Saks spend more, save more sale last week, and this bag is currently on sale.

First up, a crescent shape bag by Rebecca Minkoff. This is a very trendy style at the moment, and I like the glazed leather and the shade of brown, but I don’t care for how stiff it is. A crescent bag is a type of hobo, and it should have some slouch.

Maybe it would look better if I filled it with my things to weigh it down a bit, but I did remove the stuffing for these pictures, and it still looks kind of awkward.

I like the brushed silver hardware, though. It’s a viable option if you’re looking for an on-trend leather bag this season, but it isn’t for me.

VERDICT: This one is definitely going back.

COACH Dakota Leather Bucket Bag

at Saks // at Nordstrom // pants (29) // tee (M) // clogs (8)

Next up, a classic leather bucket bag by Coach. I really love the bucket style that’s having a moment right now, and this is a nice iteration of that trend. This one is included in the current Saks promo.

The burnished glove tanned leather has a distinct vintage flair, and it also gives it more of a timeless appeal, whereas the crescent bag is likely one that I’d only carry for a season or two.

I like the contrast topstitching and logo tag, and the two options for carrying straps. It has brass feet to protect the bottom of the bag, and the interior lining is a good quality fabric. I’d prefer microfiber or a raw leather interior, but that’s not a deal breaker.

VERDICT: Probably keeping this one. My only hesitation is, I kind of want to see the Strathberry Lana bucket bag before making my final decision. Speaking of which…

Strathberry Midi Multrees Leather Hobo Bag

at Saks // at Neiman’s // pants (29) // tee (M) // clogs (8)

Strathberry bags are a really nice bang for your buck. They look and feel more like a luxury bag, but the prices are typically well under $1000. They’re made in Spain, the materials and workmanship are simply gorgeous, and I love the classic styes. When I realized this one was part of the Saks promo, I impulsively added it to my cart. (It’s included this week, as well.)

Unfortunately, I do believe it misses the mark just by a smidge. I think it’s beautiful, and I love the design, but it seems a little too ladylike for my casual lifestyle. It’s something I’d carry to church and maybe out to dinner, but I really want a brown bag to wear with jeans and clogs and casual everyday outfits.

The color is also lighter than what I really wanted. I LOVE the color of the Coach bucket bag.

VERDICT: I’m returning this bag, but I might order the Strathberry Lana bucket bag even though it’s not on sale.

I really want to see it in person and compare it to the Coach, but I think I’ll end up with the Coach. I have a lot of gorgeous luxury bags that are on the dressier side, but the Coach has the perfect elevated yet casual vibe that is exactly what I’m looking for.

Dolman Rib Sweater Vest

at Gap (S) // PAIGE denim (29) // PAIGE wedge sandals (8) // earrings

Okay, back to clothes… I don’t know what’s going on with this sweater. It has nice details, and the overall style is on trend, but it’s huge. It went back.

CashSoft V-Neck Sweater

at Gap (S) // PAIGE denim (29) // Aquatalia boots (8) // earrings

This sweater, on the other hand, is a great basic to have in your closet, and it’s a great price. It feels soft and squishy, but there’s no cashmere. The fabric is cotton 53%, nylon 24%, acrylic 23% so perfect for those who can’t tolerate wool.

The sleeve length is quite generous, but I don’t mind that. I hate it when long sleeves feel skimpy. The v-neckline is flattering, and the traditional set-in sleeves are very much appreciated. #dropshouldersarenotmyfriend

I also tried it in brown… I love this color for fall.

VERDICT: I’ll keep one of these; I just not sure which one yet.

KUT from the Kloth Stella

at Evereve (6) // Madewell tee (M) // Vince Camuto booties (7.5) // earrings

These jeans are a nice lower priced alternative to my PAIGE Anessa wide leg crops. They have a 10 1/2″ front rise with a 27″ inseam, and I really like the wash. The front porkchop pockets are a nice modern touch, as well.

If you’re one who is always looking for a mid-rise instead of a high-rise, these might be a good option for you.

VERDICT: I don’t really need these, and also, the 6 is too small. I need the 8, but they’re a really nice option if you’re looking for a wide leg crop under $100.

Madewell Brightside Rib Split Neck Tee

at Madewell (M) // KUT from the Kloth denim (6) // Vince Camuto booties (7.5) // earrings

I got this top in both the white and the grape. I thought it would be a nice option to have – form-fitting but not skintight, and I love the split neckline. It’s actually front tucked here, but because of the shorter 21 1/2″ length, it can be worn either way.

These jeans are a little too small, so they’re making a bit of a muffin top, but this top looks better with jeans that fit correctly in the waist. I just wish it didn’t pull so much over the chest.

VERDICT: I already wore the grape-colored top, but not sure I’ll keep the white. I’m waiting to see if I need it or not.

Treasure & Bond Button Front Knit Top

at Nordstrom (S) // FRAME denim (29) // Vince Camuto boots (8)

I really wanted to like this top. The color is so nice for fall, and I love the johnny collar, but it’s so low-cut. It might look okay in this picture, but I’m not sure I can get away with it and feel decent.

The fabric is really soft, nice for the price point. I’m definitely on the fence with this one.

VERDICT: Still deciding… I guess I’ll leave the tags on and wait to see if I reach for it when the weather cools down.

KUT from the Kloth Rosalyn Trucker Jacket With Flap Pockets

at Evereve (S) // similar jeans (8) // tank (S) // boots (8)

Okay, let’s wrap this up on a high note. I LOVE this jacket. I’ve actually had it in my closet for a while, and I didn’t get pictures of it until last week.

I’m a huge fan of KUT from the Kloth utility jackets this time of year, and this one has a shorter design that is perfect for where the trends are going. It looks great with mid and high rise jeans and pants.

I love the details, the large flap  pockets, oversized buttons, the soft and stretchy fabric, the way it fits in the sleeves (not too big and no drop shoulder). Such a good jacket. I don’t expect this one to last long.

VERDICT: Definitely keeping. This jacket will be on repeat all season long!