WIW: day-to-night, Berkshires edition

A somewhat different take on the whole day-to-night outfit concept...

Last Saturday, I spent the day out in Western Massachusetts. It was blazing hot during the daytime, but in the evening we went to an outdoor concert in the mountains, which was quite a bit cooler.

For the daytime part, I wore my Allsaints sack dress with Naot gladiators and a big b/w striped hat I found recently at Target (which miraculously fits my giant head). And haha, yes that is a price tag sticking out from the back of the hat - don't worry, I removed it after I took the photo!

For the evening concert, I wanted to cover up not only for warmth but also for bug protection. So I put skinnies under the dress and a light linen jacket over the top, and swapped the sandals for oxfords. I really like how this dress looks over pants, and must remember this for the fall. Unfortunately, the bugs seem to be able to bite/sting through denim... !?! I guess it would have been worse without the jeans though!

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7 years ago

Veteran

Very inspiring! Just love it. Need to copy this for sure!
Thank you.

Brooklyn

I have a giant head too! I can never find hats to fit me. It's so frustrating, I usually end up buying men's hats. Love the way you have layered up here. The dress over denim looks really good.

Firecracker (Sharan)

This is inspired versatility! Both outfits are great. I love the simplicity of 1 and the fun layers of 2. The Naot gladiators look really cool on you, and they're perfect with the swingy dress.

viva

Diana, did you go to Tanglewood? How was the concert?

I love this hat - and it's funny because I was shopping for a hat yesterday. This floppy one looks great on you. I love the stripe, and the scale of the brim works really well. Was it hard to get used to the idea of a big hat? I ultimately left the big floppy hats at the store and went for a straw fedora. I have a very small head and hats are problematic.

You know I love a dress/tunic over pants so I love the transformation of your look from day to night. You look fantastic!!!

And it's funny but I specifically remember one night from many years ago where the mosquitos were particularly vicious and would bite through anything, even denim. I was afraid to go outside at dusk!!!

skylurker

You look so adorable in your hat.
Love the dress on its own, it looks stellar on you, and it totally works with jeans too.

Mochi

Lovely Tanglewood getup, Diana!

RobinF

Super cute - love that dress. What a great way to go from day to evening!

Anonymous

Oh, I love this change up from day to night. Both looks work superbly. Loving the hat!

Diana

Viv, the wide brimmed hat is definitely a little awkward for day to day use - for one thing i lose some of my peripheral vision. But with the size of my head, I do prefer a larger hat, and I like the drama. (Plus better sun protection!). My red hat is more useful on a daily basis - but it's also pretty big, just relatively small compared to this one. (For reference it's the same as the pink one Astrid tried recently, which she thought was too much hat). So I would say maybe start with a medium sized one and then go up to the huge one if the medium works out ok? This one is from target, which had a surprisingly good and cheap hat selection if you wanted to try an inexpensive one first.

And yes I was at Tanglewood! We go there quite a lot in the summers as my in laws have a house out there, and my husband and his family are involved with the chorus. The concert we saw that night was Tchaikovsky's piano concerto #1 and Falla's Three Cornered Hat. It was wonderful! (5 min rainstorm notwithstanding- but then again I feel like that's part of the Tanglewood experience!)

Yes. For some reason there's always a temporary outburst of rain at Tanglewood! But it's awesome there nonetheless.

Angie

(website)

Fashion Stylist

KILLER ADORABLE IN THAT HAT. I just love it on you, Diana. Fun outfits too, and great ways to take something from day to night. Nicely done.

jill58

Love Tanglewood and that's a great dress!

catgirl

Heh! This is my day-to-night situation too. Love the outfit. Gosh, I miss Tanglewood!

Roxanna

This is great inspiration - I frequently run cold and this is a great way to take something from steaming hot outdoors to indoors (which I will need next week for a conference.) Thank you for posting!

Ha - so funny about the rain! I have only been to Tanglewood twice, once with my parents and once with DH. The latter time, which was maybe 20 years ago, we were seated under the shed listening to Emmanuel Ax while a rainstorm absolutely RAGED outside. It was the most dramatic music I have ever listened to live, next to Queen, maybe ;). Unforgettable.

I'd love to get back there. You're lucky to go so often.

PS Thanks for the hat tips. I think mine is probably a wee bit small for my vaca but it's better than nothing.

Beth Ann

Great changeover, Diana. Dressing for a day like this is a common challenge for vacations -- and you've found a fabulous option!

Were you traveling by car? It's even harder when you're traveling by public transit, and how to keep all your wardobe items in a bag you carry with you.

Momo

Looks great and I love the idea.

Karie

First of all, I have met you and you do not have a big head!
Now, on to the outfits: I love summer dresses, and this one is very flattering on you. The high-low hem takes it to the next level. And what a smart idea to add jeans for the evening.
We live close to SPAC (Saratoga Performing Arts Center) and go there often for concerts in the summer, Tanglewood is also fairly close and is another beautiful place!

Yay for Tanglewood love!

Beth Ann, yes we were traveling by car. There's not much in the way of public transit out there. I would definitely not have taken the hat if we weren't driving as it's not packable at all (my red hat can get packed flat in a suitcase or bag with no ill effects so is have brought that one instead).

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