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Point of View · Aug 21, 2026

A Week of Outfits: Catskills Edition

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Emily Grady Dodge · Point of View

Hello, hello! Welcome to a week of outfits, Catskills Edition! It’s been over a year since my last trip upstate (how?), and that one was a girls weekend. This time I went with my husband and kids (they’re 4 and 7), and it’s interesting to see how that changed the nature of my outfits. No low-cut white linen dress this time! But nevertheless, I loved every costume change—and there were many. So let’s get to it!

For the drive up, which is about 2.5 hours, I went with my new pants and my favorite top of the summer. This shirt works (for me) sans bra, so while this outfit looks dressy for a drive IMO, it was the most comfortable thing I can imagine wearing. Plus I had main character energy at every rest stop and for a visit to the World’s Largest Kaleidoscope. That might be the weirdest sentence I’ve ever typed.

ICYMI, I announced recently that I’m no longer accepting gifting. These sunglasses were the last gifting hurrah, and honestly? I still prefer my tried and true Ray-Bans. But these felt like a fun thing for Vacation Emily. I’m picky AF about sunglasses and these were comfortable and the color tint is great. I lived in them all weekend, but I don’t think I would have gone out of my way to buy them if they hadn’t been given to me. Take from that what you will!

We made it! We stayed at Wylder Windham and it was the perfect family-friendly getaway. The grounds are beautiful and very well-appointed. We will definitely go again next summer.

God, I love an Adirondack chair.

After check-in we wandered around a bit to scope it out, then went to the room to unpack. Aside from what I wore, I brought:

As you’ll see below, I wore every item and it felt like the perfect amount for a very casual three day trip.

This is the second hotel I’ve stayed at designed by Post Company, and they really nail it. As a self-proclaimed design-nerd, I took a million photos of every detail. This view from the main lodge overlooking the pool, complete with a cafe curtain, really sealed the deal for me. A true vacation for my eyeballs.

More photos of the lodge. Behind me were game tables- my kids particularly liked getting lemonade from the front desk then sitting down at the chess table and “playing.” I think they did that about ten times over the course of the weekend, ha!

Quick change into swimsuits and over to the pool! After swimming, we showered and then went “into town” (a four minute drive to Main Street) for pizza and I wore the exact same thing I had on earlier. Back at the hotel, we made s’mores at the fire pit and hung out in the hammock. Perfect day!

Early morning run to the bakery for coffee and chocolate croissants! I only packed one pair of shoes, so I threw those on, along with my CoH cargo pants and my favorite grey sweatshirt (thanks for the rec, Anna Newton!). Easy and comfortable.

P.S. the full length mirror situation in the room was.. less than stellar.. so I had to resort to the upside-down-phone-selfie for the trip. You’ll have to trust me that I had the aforementioned sunglasses on pretty much 24/7 as well. Even inside.

Back at the pool!

I brought two swimsuits (green and black) and this pareo, and that’s all I needed. Well, and my flip flops, earrings, and a claw clip. And a latte. And my free-with-subscription Arch Digest tote bag.

Changed for lunch! I love this outfit- I wore it to the zoo recently and wanted to repeat it. I’m not scared of wearing white around my kids because a) stain remover b) lived in clothes look cool. This is another top I can skip a bra with, and I just use these instead. Pants are these and I love them!

Closest to a mirror selfie I got all weekend.

We walked over to another hotel to check out their restaurant - the interiors were very good, but the food was just ok. Oh well!

Sitting in a chair to supervise “chess,” and my mind wandered to the paint strategy. First of all, I think the grey is a perfect color and I’m fairly convinced it’s French Grey from F&B. I told my husband I should start traveling with my paint deck so I can color match on the go, as I love the idea of using paint colors as a souvenir of sorts. Like, oh yeah, my bathroom is the exact color of the wood fence at the restaurant we go to at Lake Tahoe. Cool or crazy?

Ok but look- the ceiling and crown molding are this grey-green color (full gloss) and then the walls are white, but then the ceiling color continues down on the built-ins only (eggshell). Brilliant.

We went swimming again, then back to the room to shower and get ready for dinner. I repeated the pants from earlier, but it was getting chilly out so I swapped to a grey tank and put my sweatshirt over my shoulders. I love the grey against the creamy off-white pant color.

My tank is old from AMO, but I really like this one from Almina. It looks almost identical.

The real MVP of my summer wardrobe!

Nothing better than going to dinner with wet hair while you’re on vacation, right?

Another morning, another jaunt to the bakery. Silk pants + grey sweatshirt = yes.

Back to the pool with a late check-out secured!

Please indulge me in sharing one more photo of the property. I managed a million of those, but I failed to take a photo of what I changed into for the drive home. These pants and this top (in black). No notes!

Bye, Wylder! We’ll be back :)

Back to reality! I wore this top1 and jeans to drop off my kids at their day camp, but when I got home I was feeling the post-vacation blues and couldn’t shake how blah I felt. So I put my hair up, which helps sometimes, and put on these earrings that I haven’t worn in awhile. Immediately felt better!

Shoes are TKees, which I’ve had for four summers now. Clutch is Celine Macadam off TRR— but there are tons of them on the secondhand market and it’s such a great piece to own.

Favorite pants! Every time I wear them I’m so happy my pal Jordyn Sharfe encouraged me to get them. I know they’re expensive, but they’re so well made and I love wearing them. I’m still watching TRR like a hawk for a white pair. It WILL happen.

I worked from home in this outfit, but threw a blazer over my shoulders for my zoom meetings. I tend to keep one on the back of my desk chair so I have it ready at a moments notice. Life hack?

Guess I’m into tonal outfits! Navy on navy is really my favorite, but don’t tell my other clothes. I went with a necklace* and skipped earrings, and then kept it minimal with my shoes. Love this outfit—I’ve worn it before and I’ll wear it again!

Well, that was a fun week! Thanks for re-living it with me and letting me talk about what I wore. As always, let me know if you have any questions in the comments :) Happy to chat sizing, etc!

Talk soon!

Emily

please note - some links do create affiliate revenue for me, at no extra cost to you. anything previously gifted is marked with an asterisk. thank you for your support!

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It’s sold out from Buck Mason, but I’m hunting for good alternates for next week’s post!

Read the original on emilygradydodge.substack.com

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