Photo by Michael Piazza; the patio at “Craigie Next Door” at Craigie on Main, Cambridge

Let’s face it, the run of warm, dry weather we’ve enjoyed this fall has been pretty great for outdoor dining. Evenings with temps in the 60s with little to no rain may not be so great for farmers, but they’re perfect for patio cocktails at golden hour and suppers on the sidewalk. Who knew a drought could be a boon for the restaurant industry? Just imagine how many more closures we’d be seeing if we’d had anything near our typical autumnal rainfall.

But with the chill of November on our doorstep, a perfect storm is brewing: Winter’s coming, cases are climbing and unless we keep dining outside, the restaurant industry could be doomed. Not to imply that restaurants are in a good position at the moment—they’re obviously not. They desperately need government assistance pronto, but without the sidewalk parklets and heated patios they’ve been able to fill duing the warmer months, things would look a lot more bleak. If we want a robust and funky food system on the other side of COVID, filled with diverse and eclectic cuisines cooked by talented, committed chefs, we are going to have to mask up, dress for the weather and commit to outdoor dining as long as we possibly can. We’re Bostonians, after all—we’re used to the cold. We can do this.

Enter my chicest friend, Alisa Neely, Best of Boston-awarded fashion stylist and owner of styleScout. After multiple patio dinners dressed for the “before times,” with ankles left bare under the table and the wind blasting through my sweater, I needed some help. Surely she’d know how I could keep snuggly warm on the patio without looking like I’d dressed for a day hike.

Alisa’s aesthetic toes the line between high fashion and street style, steering her clients towards wear-forever investment pieces as easily as trendsetting wardrobe boosts, with elegant add-ons to make any look right for right now. I knew she’d have the best read on how to dress for this unique moment in time.

Her brilliant suggestions—some high-end, some mid-range and a few budget options, including a handful sourced from local boutiques—are just that: suggestions. Since my wallet’s been feeling lighter during this economic downturn, I’ll mostly be “shopping” my own closet, putting together outfits using Alisa’s recommendations as a guide. But those shearling lined boots are definitely calling my name…

SARAH BLACKBURN: Alisa! I can’t think of a better person to help me navigate this season of cold outdoor dining. We’ve been going out to dinner more often than usual lately—it’s so nice to get out of the house and away from our desks, and “date night” feels vaguely normal at a time when everything is so in flux. But I’m always chilly! My cute jacket-sweater-scarf combo isn't cutting it anymore, even with heated patios. How can I stay warm and still feel like I've dressed for a special occasion?  

ALISA NEELY: The best way to stay warm is and will always be layers. I love the idea of wearing a skirt with nice warm woolen tights and boots paired with a bodysuit, an oversized sweater and a gorgeous long coat.

SB: Some of the most interesting dining out we've done this fall has been at farms, breweries and wineries—the vibe is casual, there are fire pits and Adirondack chairs, the food is delicious and the drinks are plenty. But it can get really chilly out in an orchard, even on a sunny, autumn afternoon. What do you suggest I wear—and bring—for these more casual outings?  

AN: Fall is the perfect time in New England to indulge in the amazing farms, wineries and breweries throughout the region. You can't beat the incredible views and the full color display Mother Nature puts on for you. What I suggest for these crisp outdoor days is something that can withstand a dirty bench and soft muddy grounds, and a little advance planning can make all the difference. Pack a bag for your car, kitted out with a thick wool blanket, a scarf, a chic little hat and some gloves—you’ll be ready for anything.

SB: When I really bundle up with a big, warm wrap at the table, I’m always afraid I'll spill on my nice woolens. What do you suggest for keeping my neck warm without dunking my scarf in the soup? 

AN: These cashmere gaiters do the trick without adding a lot of bulk. I am always a fan of turtlenecks under sweaters or blazers to add that extra layer of warmth.

SB: Let's talk footwear: My feet get COLD under the table! What can I wear that is fun, chic and most of all WARM as we head into winter and still want to eat outside?

AN: Wool and cashmere socks under a chic tall boot will help, and you can take a tip from the ski community and throw in a hand/foot warmer right when you sit down; it should last at least until the cocktails kick in (order them in bulk and keep the box in your car!). I have also loved the No. 6 Clog boot for a long time, which is a much chicer option then the overly popular Ugg boot. I go for the ones with the shearling lining so my feet stay surrounded in warmth. Here are some other great shearling lined boot options.

SB: I can't tell you how many cute masks I have bought—and lost—already this season. Do you have suggestions for some cheap-but-chic cotton masks that won't break the bank?

AN: Anthropologie has this cute set (below left). I also really like the simplicity of these linen face masks from Etsy which come in a variety of colors (below right).