Starting off with my trip to New York City, it was a dreary day and there was even a slight chill in the air, so I took advantage of the opportunity to wear one of my more “transitional” tops. (I brought a big suitcase because I had packed a bunch of outfits to shoot the next day.)

I love the combination of chestnut brown and sky blue stripes in this sweater, and it has a flattering v-neck and a cropped fit, perfect for pairing with high-rise wide-leg jeans, like the PAIGE Anessa. (I have no idea why they call them straight; the Anessa is a wide leg style, but it does fit closer to the leg than some, which is why I like it!)

EVEREVE Aiden V Neck Vest (M) // Paige Anessa 31″ (29) // Jeffrey Campbell Fathom Ballet Flats (8.5) // Mulberry Small Amberley Leather Satchel // AWAY The Medium // AllSaints necklace // similar hoops // Yurman bracelet

I chose the tan Jeffrey Campbell Fathom Ballet Flats because they almost match the sweater, which creates a nice bookend to the look. I love the shape of these shoes, too. It feels very now.

To top it off and keep me warm and dry, I wore my new London Fog rain trench from the #NSale, which is back on sale! It worked perfectly with this outfit and kept me dry in the drizzle. The shoes, on the other hand, weren’t the most practical choice… but I survived!

London Fog raincoat – on sale! (S) // EVEREVE Aiden V Neck Vest (M) // Paige Anessa 31″ (29) // Jeffrey Campbell Fathom Ballet Flats (8.5) // Mulberry Small Amberley Leather Satchel // AWAY The Carry-On in Sand // Goyard tote

That night, I had plans to go to a cool bar uptown, so I changed into an all black outfit. I really wanted to wear these leopard slingbacks, but it was raining cats and dogs by then…

EVEREVE Bevan Crew Neck Sweater (M) // Paige Anessa High Waist Ankle Wide Leg Jeans (30) // Paige Wren Slingback Pumps (8) // Celine box bag (similar for less at Quince) // similar bracelet // Jenny Bird earrings

So, I went with wedge sandals that seemed more weather proof, although my feet did get wet. Once again, not the wisest footwear choice! I had leather boots with me, but they seemed silly in August, and we were taking an Uber, so I figured I’d be fine. I guess I’m out of practice with NYC dressing because I saw plenty of boots out and about that night. Oh, well!

EVEREVE Bevan Crew Neck Sweater (M) // Paige Anessa (30) // Tory Burch sandals (8) // Celine box bag (similar for less at Quince) // similar bracelet // Jenny Bird earrings

For my ride home the next day, I wore the same blue jeans as the day before, but I threw on this chocolate brown cashmere sweater vest that I had brought along, and I wore leopard mesh Mary Janes instead of the ballet flats. The rain had stopped overnight, so the mesh wasn’t an issue, and I love how the pattern adds interest to the look. Plus the shades of brown work in beautifully with the sweater.

Nordstrom Cashmere V Neck Vest (S) // Paige Anessa 31″ (29) // Dolce Vita Roslyn (8.5) // AWAY The Medium // Goyard tote // SHASHI Bangle Set // Baublebar necklace // Jenny Bird earrings

I broke out my new rust-colored kick flares to run some errands and go to the nail salon the next day. I love this rust-and-oatmeal color combo, and I went with taupe shoes and bag to keep it light for summer.

LOFT wedge sweater (S) // KUT from the Kloth Kelsey (8) // Dolce Vita Lorene T-Strap Sandals (8) // similar YSL camera bag (similar for less at Quince) // Jenny Bird Large Aurelia Hoop Earrings // Jenny Bird Ola Bangle

We met friends out for dinner that night, so I added some bolder jewelry and a pair of wedge sandals.

LOFT wedge sweater (S) // KUT from the Kloth Kelsey (8) // Paige Jill (8) // similar YSL camera bag (similar for less at Quince) // Jenny Bird Large Aurelia Hoop Earrings // Jenny Bird Ola Bangle // Baublebar necklace

Paul took this photo with his iPhone when we were walking to dinner. The lighting was amazing! I was wishing I’d brought a few more outfits to shoot, haha!

LOFT wedge sweater (S) // KUT from the Kloth Kelsey (8) // Paige Jill (8) // similar YSL camera bag (similar for less at Quince) // Jenny Bird earrings // Jenny Bird bangle // Baublebar necklace // Tom Ford sunnies

I wore this casual look to go shopping at REI, looking for Iceland gear. I love a good graphic tee, and this one is so soft, but it’s pricey. I got mine on sale.

MOTHER Tee (sold out, options) // Paige Leenah Ankle (29) // Birkenstock Madrid (39) // Jenny Bird Tome Hoops – Small

And this was a recent church outfit. I figured I didn’t have much time left to wear my light-colored linen tops, so I wore this Rails blouse one last time. Once September rolls around, I usually pack my linen away.

Rails Arlene Top (S) // MOTHER Weekender (30) // Dolce Vita Mylee Heels (8) // similar bag // similar raffia earrings // similar bracelet // Anna Beck necklace

The next day, it was time for my next adventure—Caroline I flew to Nashville to visit Becca and see the Dolly musical. I busted out the rust-colored jeans again to wear for our flight down, and this time I paired them with a chocolate brown top. I think this is such a fun color combo for this transition season.

I also wore the mesh leopard Mary Jane flats for some pattern and texture. Once again, they work as a bookend to the look, tying it all together nicely. I added brown and beige raffia hoop earrings and a dark brown resin bangle to accessorize the look, and I brought along my new cloth & stone zipper shacket. It came in very handy on the plane!

cloth & stone zipper shacket (S) // Paige Syrie Top (M) // KUT from the Kloth Kelsey (8) // Dolce Vita Roslyn (8.5) // Clare V. Midi Sac // raffia earrings // SHASHI bangle set

Once we arrived and got settled into our hotel room, we walked down to Broadway to find some live music. (Kid Rock’s Honky Tonk never disappoints!) I changed into sandals because my feet were hot and tired of wearing the Mary Janes. Plus it was quite warm in Nashville, so sandals seemed to make more sense. After that, we came back to our room and rested for a bit, and then headed back out to meet Caroline for dinner.

Paige Syrie Top (M) // KUT from the Kloth Kelsey Kick Flares (8) // Kaanas sandals (8) //  Clare V. Midi Sac // raffia earrings // SHASHI bangle set

The next morning, I went over to Belmont to have coffee with Becca before her first class. I wore this trusty outfit combo again, this time with sandals.

EVEREVE Aiden V Neck Vest (M) // Paige Anessa 31″ (29) // Kaanas sandals (8) //  Clare V. Midi Sac // Jenny Bird Florence Earrings // similar bracelet

Afterwards, I came back to the hotel and changed into the leopard flats to go shopping with Caroline. (I kept changing shoes to try and keep my feet from getting blisters. I don’t know why I didn’t pack a pair of sneakers! There is so much walking in Nashville.) I also added a necklace to jazz up the look a bit!

EVEREVE Aiden V Neck Vest (M) // Paige Anessa 31″ (29) // Dolce Vita Roslyn (8.5) // Clare V. Midi Sac // Jenny Bird Florence Earrings // similar bracelet // T-Bar Pebble Pendant Necklace

That was the night of the Dolly musical, the impetus for our trip. I did not have Dolly-themed attire, so I just went for a simple all black look. I wanted to wear my gold block heeled sandals, but I went for the flats because I knew we’d be doing a good bit of walking.

EVEREVE jacket (M) // EVEREVE Bevan Crew Neck Sweater (S) // Paige Anessa (30) // Kaanas sandals (8) // Celine box bag (similar for less at Quince) // Jenny Bird Large Aurelia Hoops // similar bracelet

Here’s a picture with Becca in front of the Fisher Center, where we saw the show… Caroline was off getting a coffee at the time, so I don’t have a picture with her, sadly. I did get a cute one of the two girls in Becca’s dorm room, though.

And just like that, it was time to head back home! I wore the rust jeans and leopard mesh flats again, this time with the oatmeal sweater. Both times, I did end up wearing the jacket once I got to the airport, but I never got a picture with it, sadly!

cloth & stone zipper shacket (S) // LOFT wedge sweater (M) // KUT from the Kloth Kelsey (8) // Dolce Vita Roslyn (8.5) // Jenny Bird Large Aurelia Hoops // Jenny Bird Ola Bangle //  Clare V. Midi Sac // AWAY The Carry-On // Goyard tote

Back at home the next day, I wore this henley sweatshirt and the light wash wide leg jeans with patch pockets. I really like this color combo, for some reason, and this sweatshirt is one of my favorites. I always get compliments on it. It’s just such a fun color, and the design is interesting while still simple enough to not feel extra.

EVEREVE Zuri Sleeveless Henley Sweatshirt (M) // KUT from the Kloth Meg with Patch Pockets (6) / /Birkenstock Madrid (39)

I had a photo shoot the next day, and this was the last outfit we shot, so it’s what I wore home and for a few errands along the way.

Paige Syrie Top (M) // KUT from the Kloth Kelsey (8) // Dolce Vita Roslyn (8.5) // Clare V. Midi Sac // raffia earrings // similar bracelet

I threw on this simple look last Saturday. I pretty much just worked from home all day, although we did end up visiting with friends that night.

EVEREVE Teddy Washed V Neck Tee (S) // similar MOTHER Weekender – 40% off! (29) // beek Sunbeam Flip Flops (8)

It was getting chilly that evening, so I pulled this cozy hoodie on over top.

Sarasota hoodie // similar MOTHER Weekender – 40% off! (29) // beek Sunbeam Flip Flops (8)

I pulled out this green cowl neck top from last year and paired it with chocolate brown utility pants for church on Sunday. I wore the gold sandals to lighten it up a bit, since it was still August, after all.

Michael Stars Nara Mock Neck Top (S) (other colors available at Michael Stars and Zappos) //  Paige Anessa Utility (29) (option) // Reformation Eleonora Slingback (8) // Jenny Bird Large Aurelia Hoops // Jenny Bird Ola Bangle

We went out to dinner a little later on, and I changed into jeans and flats to be more comfortable walking around town. This time, I added a belt, which I think is a much needed point of interest, and it helps to break up the look a bit.

Michael Stars Nara Mock Neck Top (S) (other colors available at Michael Stars and Zappos) // Paige Anessa 31″ (29) // Nili Lotan belt (M) // Dolce Vita Roslyn (8.5) // similar bag (also here) // Jenny Bird Large Aurelia Hoops // Jenny Bird Ola Bangle

And then it was back to one of my favorite graphic-tee-and-denim outfits for a long Monday working from home.

MOTHER Tee (sold out, options) // similar MOTHER Weekender – 40% off! (29) // beek Sunbeam Flip Flops (8) // Jenny Bird Tome Hoops – Small

I didn’t bother taking any pictures yesterday, as it was another day at home, but I wore my olive green Athleta Brooklyn Heights Cargo Pants and black Getaway Linen Blend Muscle Tank, along with my new Flipflops (thanks to a reader recommendation!) I plan to bring them to Iceland for wearing around our hotels, as well as for any pool or hot tub situation that might arise!

And that’s a wrap… The next What I Wore Lately will be full of outfits from Iceland, Scotland, and London. It’s hard to believe our trip is so close! In the meantime, I hope this post gives you some ideas for shopping your closet and putting outfits together in new ways during this tricky transition season.