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What to Wear When the Calendar Says Fall but it Feels Like Summer

My Jewish readers know the drill. Are the High Holidays early this year? Or late? It’s always a question, year after year. Because unlike Christmas that falls on December 25 every single year, the Jewish calendar is lunar. So our major holidays are always changing. For instance, in 2016, Rosh Hashanah began on October 2, and Hanukkah was on December 24. This year Rosh Hashanah falls on LABOR DAY!! Like, the actual Monday of Labor Day, AKA the official end of summer. According to some outdated fashion rule, it’s also the day you have to stop wearing white clothing (until the next summer, marked by Memorial Day). Just as an aside, I think that rule is total rubbish and you do not need to follow it. But that’s probably more for another column.

Anyway, Rosh Hashanna, for me, marks the beginning of autumn. It’s the big fall kick-off. The Jewish holiday version of the September issue of Vogue. In fact, as a girl, when my mom would take me on our annual back-to-school clothes shopping outing (because back then it was a good thing to outgrow your clothes each year – at my age now, not so much!) One of the most important items to check off the list was a new Rosh Hashanah outfit. 

Rosh Hashanah Usually Means Fall Clothes

Normally, my New Year’s outfit (Rosh Hashanah is considered the Jewish New Year) would be in a fabric or color that felt like fall – think wool, corduroy, or velvet and in colors like brown, camel, or burgundy. Nice rich colors and fabrics that are on point for colder weather. The same way there are distinct foods one associates with certain holidays that make it “feel” like that occasion, so too with specific garments.

I vividly remember the feeling of wearing my new outfit to every Rosh Hashanna family dinner and then to synagogue. And then I’d wear it again for the school holiday concert and any other colder weather events we had. Until, of course, it was time to shop for my new spring outfit (this time it was for Passover).

This shopping ritual to mark important milestones is not just a “Jewish thing.”  My Christian friends had similar seasonal shopping experiences. However, their touchstone holidays were usually Christmas and Easter. Ya know, same song, different tunes.

But, It’s Labor Day!

But this year, with Rosh Hashanah landing literally on Labor Day – a day I think of as reserved for pool parties and backyard BBQ’s – it’s throwing the whole what-to-wear, fall-debut, thing off. Big Time. Personally, as much as I might sacrifice comfort for fashion on occasion, wearing wool tweed when it’s 80 degrees outside is a definite NO in my book. Honestly, I’m sweating just thinking about it.

So the big question is what are we to wear for Rosh Hashanah 2021? The answer: something that’s covered but lightweight. Breathable for outside but can keep you warm in the air-conditioned synagogues. And is on the more modest side, because, let’s be honest, what we wear to a  house of worship should be slightly more conservative than what you’d wear to a club.

Ok, so let’s chat about how to ring in fall and the new year (this year it’s going to be 5782!!) and not melt…

And, BTW, this styling tip is not only for my Jewish readers… there are all kinds of events (work-related, family festivities) that happen when we think it’s autumn, but the thermometer says otherwise. This type of transitional dressing works really well for fall and for spring – the times when it’s usually the hardest to get dressed.

Anthropologie, There’s a lot to Love right now

Back in June, I wandered into our local  Anthropologie and actually walked out with a big old bag of clothes! For myself that is! That doesn’t usually happen for me there. The Anthro aesthetic is somewhat girly and romantic and that’s not typically how I’d describe my vibe. Don’t get me wrong, I have a ton of success there with my clients whose style falls in the elevated boho and feminine realm. But for me, personally, the pieces never really become part of my repertoire… Until now.

I’m not sure if they’ve changed or I have…I used to go into Anthro and everything I put on felt like I was wearing a costume. Again, I loved it on other people, but I felt like I couldn’t pull it off. In the last couple of seasons though, the collections feel a little more toned down and tailored. Some things even border on edgy. At the same time, my horizons are expanding. Adding details like color and patterns seems fresh these days. My inner boho has been set free!!

Basically, I’ve been living in (and loving) my haul from earlier this summer. The good news is many of the items are still available AND a lot are even on sale!! Stores are gearing up for fall with cashmere and cords, but there’s a lot of warmer weather still to be had, even for those of us that live in the snow belt!

Anthropologie Late Summer Haul (and Sale) Picks