8 Cute, Warm Outfit Ideas for Dining Outside When It's Cold

I never thought I'd be writing about the predicament of what to wear to dine outdoors in the winter (because who does that?), but it's our reality in 2020, so here I am to give you some advice. First and foremost, it's up to each of us to decide what level of risk we're comfortable taking during the COVID-19 pandemic. Especially with case counts rising yet again, it's safest to stay home. But dining outdoors is indeed safer than dining indoors, so for those who choose to go to a restaurant, many are opting to take advantage of the plentiful outdoor seating around the country. I, for one, have dined outdoors in 100-degree heat with flies swarming and in the rain this year, so I guess my next adventure is dining outside when it's 40 degrees. But it's going to take a little preparation, so let's discuss it.

As someone who is always freezing, I think I'm well-suited to speak on the topic of dressing for warmth without sacrificing your sense of style. The thing that makes outdoor dining in the winter such a challenge is that you can't sit there and eat your soup in a puffer and scarf and not be uncomfortable (but if you can, tell me your secrets). You're going to want to wear warm base layers and choose your outerwear carefully, and hopefully, there will be heat lamps. To guide you, below you'll find eight perfect outfit ideas for wintertime outdoor dining, along with a tip to glean for each and what to buy to see you through to next spring. Good luck out there, and don't forget your mask and this genius electric hand warmer.


Outfit Tip: Wear Warm Accessories
(Image credit: @aemiliafay)

My friend (and former Who What Wear editor!) Aemilia is my outdoor dining muse with this look. Note the hat and cozy socks. Chic, warm accessories are key here. You want to leave as little skin as possible exposed. And of course, don't forget a warm mask. (I love this knit from Lisa Says Gah!)


Outfit Tip: Top a Sweater With an Oversize Blazer
(Image credit: @champagnemani)

What we're going for here is outerwear that you don't need to take off when you sit down to dine. An oversize blazer is perfect—just make sure that your sweater is warm and that your blazer is made of wool or leather.


Outfit Tip: Order a Shacket ASAP
(Image credit: @claire_most)

Shackets are a trend this season, and they happen to make for a great non-bulky jacket. Opt for one that's made of wool or thick flannel, and if you want to wear a coat over it, make sure it's a little more slim-fitting like the Reformation one below.


Outfit Tip: Wear a Sweater That's Heavy Enough to Sub for a Coat
(Image credit: @annelauremais)

This won't work in all climates in the middle of January, but when feasible, skip the coat and wear your warmest, wooliest sweater (preferably with corduroys). 


Outfit Tip: Turtlenecks (and Scarves) Are Key
(Image credit: @lefevrediary)

No matter what you're wearing, if your neck is cold, you will be cold. Fix that with the help of a turtleneck or a scarf (preferably one that's lightweight and warm so you don't have to take it off to eat).


Outfit Tip: Skirts and Dresses Call for Tights and Knee-High Boots
(Image credit: @asos_lotte)

This is a no-brainer, but if you must forgo pants this winter, cover your legs as much as possible, preferably with a pair of Uniqlo's famous Heattech tights. And luckily, knee boots are ridiculously chic.


Outfit Tip: Wear a Wool coat for warmth without bulk
(Image credit: @annabelrosendahl)

A wool coat just might be your hero piece this winter. Unlike a puffer, if it's roomy enough, it's not all that unheard of to keep it on while you dine. Just keep your layers thin so that you can move your arms to eat.


Outfit Tip: If You Must Wear a Puffer, Wear a Warm Sweater
(Image credit: @tylynnnguyen)

If it's cold enough to require a puffer, it's cold enough to need a thick sweater. Wear your thickest one with a Uniqlo Heattech layer underneath so that you can take the puffer off at least for as long as it takes you to eat.

Next up, eight non-aging style tricks I follow in the winter.

Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.