Tuesday, October 7, 2014


As anyone will tell you, I'm not shy about extolling my love for the month of October. Selfishly, it's my birthday month (29 is comin' in hot...), but it's also undeniably the most beautiful time to be in New York. It's a great time to walk the streets, eat outside and spend time in Central Park. It's also a great time to escape the island and head upstate to look at trees and frolic around an orchard.

Oh yes, it's apple picking season. Fall's most Instagramed activity hits its stride this month, which I think causes a lot of upstate-bound gals to go into a tizzy over what to wear. On one hand, I get it. We wear pretty much the same thing over and over again in the city, and the countryside sort of begs for you to get into character a little. On the other, I think you have to be really real with yourself about this 7-hour experience. If you're going to shop, be smart! If you're going to shop your closet, don't over-think it.

Thus, my best advice for dressing for apple picking like a real person. But, a real person who likes to look good and get a little festive when the occasion calls for it. I'm heading upstate for some apple-picking myself this weekend (it's what Meghan calls a #falliday), so I'm already starting to mentally browse my wardrobe for appropriate attire. (Oh, and if you're wondering, yes, I was rather inspired by this pretty silly and expensive slideshow from ELLE.)

Apple Picking Like A Realist

1. Be smart about your layers. The temperatures in October are unpredictable. It could actually be like 70 degrees out there, so don't force the wool sweaters, fur vests and blanket scarves. Play it by ear. No one will doubt your appreciation for fall if you just throw on a plaid shirt with your jeans and boots and call it good. That said, if it is going to be chilly, bring something you can also tie around your waist for a little trendy-meets-practical moment. If you're desperate to treat yourself (trust me, I've been there) and worried it might actually be freezing, why not pop over to Uniqlo for a slouchy men's lambswool sweater? Inexpensive and still amazing, and will look perfectly cool with skinny jeans and a great hat.

2. The Bean Boots thing is real. Even if it hasn't rained in a week or two, you can bet it will be mucky out there. Spare your nice leather boots the drama and wear something more practical. You know I worship at the alter of the 8" L.L. Bean Boot, but your Hunters will do, too. 

3. Work with what you've got. Personally, I've got a great pair of black denim overalls from Paige that haven't gotten enough wear, so I might want to take them for a spin. (Too #farmerchic?) Would I buy some just for an apple picking #ootd? Please. If you're really lacking in a perfect plaid shirt for fall, then this is actually a good excuse to get one. Yes, it's festive, but it's also something you can wear until March. I like this black-and-white buffalo check shirt from J. Crew because it's thematic and warm, but also not so cutesy-woodsy that you couldn't tuck it into a pencil skirt or leather pants and wear it to work on Monday. 

4. Hats are the best. You can pull together a festive fall outfit with what's in your closet now, but I will always advocate for a felt or wool wide-brim hat if you don't have one. They are hands-down my favorite fall accessory. I still wear the one I bought three years ago from Madewell (long gone, but find a similar one here), and my girl Megan Collins (of Style Girlfriend) raves about the quality and fit of her Rag & Bone topper.  (See also: an inexpensive option from Forever 21.)

5. Pack the good stuff. Note: This has nothing to do with fashion, but it's important. No matter where you go, whether it's a tour of multiple spots or a one-destination apple-gathering extravaganza, there will be cider, but there will not be booze. There may be wine, but there will not be whiskey. Personally, I could give a hoot about bringing home a load of apples I'll never bake into a pie. However, I do like to wander around orchards, observing the foliage and ride in the back of a tractor-trailer with a little buzz on. Bring a bottle for the bus/train, and fill your flask for the walk. Find the nearest cider stand (there's always a cider stand) and have yourself a delightful little nip. Cheers!

Image credit: My post from a trip to Vermont in 2012


  1. Great ideas! x

  2. The chicest outdoor look ever! Thanks for sharing!

    Love, Jamie Herzlinger