Expert Advice: Holiday Picks

Expert Advice: Holiday Picks

Plus gift advice

Everyone has their own holiday traditions, whether it’s celebrating with your favorite winter cocktail or chilling out with your go-to winter movie. We asked our five style editors to tell us their top holiday picks, from what boots they want to find under the tree, to their favorite wintry activities (and yes, eating apple pie does count as an activity). Oh, and in case you missed it: everyone is listening to Adele.

Jess Kirby


I want the Ashdale All-Fit Tall Waterproof Boots because they are comfortable, warm and chic. I would wear them to a football game outdoors or when doing some holiday shopping around town.

I need the Sea Street Country Pom Beanie because I love a chunky knit beanie in a neutral color. This one would match my entire wardrobe.

I love the Mirey Brook Sweater because I can’t get enough of turtleneck sweaters this season. Tucked into ripped jeans, over a shirt or with a skirt - it’s my favorite everyday piece.

I want the Sea Street Waffle Knit Mittens because my hands are always cold and these ones are so cute for long walks, I would keep them in my purse, just in case.

My favorite drink this season: The same as every season – a margarita. Seriously, why not?

My favorite food this season: Warm brie with honey drizzled on top.

My favorite book for this season: The Polar Express. It’s my childhood favorite, but I still love it.

My favorite album to listen to in December: Adele’s new album ‘25’. It just came out but I have probably listened to it a thousand times already.

My favorite winter activity: Snowboarding or pond hockey. Nothing better than a day on the slopes or playing a game of pick up hockey on the pond with friends.

The best gift I've ever received: My great aunt gave me a vintage amethyst ring. I wear it every day.

My advice for picking a good gift: Choose something personal and special, that they’ll not only be able to use, but they’ll have for years to come. 

Laura Gonzalez


I like the Rosebrook Waterproof Trench Coat because a classic trench is always a must. In San Francisco it would be great to wear for walks around the marina.

I need the Cilley Leather Shopping Bag. The classic silhouette on this handbag would complete any outfit. Its size and the fact that it has many compartments would make it a great work bag.

I love the Whittemore Chelsea Boots because what can’t you wear with Chelsea boots? They are the most understated and most versatile boots! Pair them with ankle length denim and an oversized knit sweater for a perfect brunch outfit.

My favorite drink this season: Good ol’ hot chocolate.

My favorite food of this season: My grandma’s apple pie. She has a secret recipe that she only makes at Christmas, making it extra special.

My favorite book for this season: I always find myself reading The Harry Potter books around the holidays.

My favorite album to listen to in December: Adele’s new album ‘25’. I’ll been listening to it non-stop throughout December…because hello? It’s Adele.

My favorite winter activity: Spending the weekend in Lake Tahoe with family. We rent a cabin and go skiing and snowboarding.

The best gift I've ever received: When I was 8 and my mom’s boyfriend dressed as Santa and surprised all the kids. We didn’t even pay attention to our gifts we were so excited! Looking back now, I am really grateful our family planned that for us – it’s honestly the best gift I’ve ever received.

My advice for picking a good gift: Have your loved ones make a list and choose from their lists. They get something that they want and still get to be surprised at what you chose.

Edison Gonzalon


I want the Premium Waxed Car Coat because it would go with everything. For a dapper look I could wear it over a suit, or for a more casual look I could pair it with some jeans.

I need the Adkins Leather Duffle Bag because it’s an essential. You could take it as a carry on when you’re traveling or to a business meeting. It’s a simple bag but that's what makes it so classic.

I love these beautiful 6-inch Nubuck Wheat Premium Waterproof Boots because they are a timeless classic. They will never go out of style and you can wear them in every season. They are just so comfortable.  

My favorite drink: A hot mocha chocolate . I've always been a chocolate lover, but the mocha flavor just gives it an extra kick.

My favorite food of the season: A Spanish dessert called Arroz Con Leche (rice pudding). My mom makes it, and it’s so delicious. Everyone should try it.

My favorite album to listen to in December: Since Adele's new album (25) it's coming out I think I’ll be listening to that a lot this season. She's an amazing singer and songwriter.

My favorite winter activity: I love to go to the movies all year round. I mean, who doesn’t love the movies?

The best gift I've ever received: I think the best gift I receive every year is having my family all together. My family is so important to me and I wouldn't trade that for anything.

My advice for picking a good gift: My advice is just enjoy the company of others. Show your love ones that you care for them, not only with gifts, but actions. 

Aaron Wester


I want the Men’s West Haven Waterproof Chukka Shoe (similar here). The full grain leather give them a rugged, well worn feel. I’d get them in dark brown because they’ll go with everything.

I need the Bass River Wool Blend Shirt Jacket because it’s a perfect layering piece between seasons. It’s heavy enough to be worn as outerwear in the fall, but you can layer a coat over it in the winter. Plus, shackets are the new jackets.

I love the Mount Major Shearling Leather Jacket because it’s a killer jacket. Shearling is an investment that only gets better with time. Plus it’s crazy warm.

My favorite drink this season is mulled cider with whiskey. It’s my version of a holiday ‘spiced’ drink.

My favorite dessert this season is pumpkin pie. You can’t mess with a classic.

My favorite book this season is “Mockingjay” from The Hunger Games trilogy. I’m a sucker for a good action story (and yes, you should read the book before you see the movie – always).

My favorite album to listen to in December is “Wilder Mind” by Mumford and Sons. It’s haunting melodies are the perfect soundtrack for cold winter days.

My favorite winter activity: Skiing! I love hitting the slopes.

The best gifts I have ever received: Experiences, rather than objects. My partner plans huge adventures and special nights for my birthday and the holidays. Experiencing something new with someone I love is the best gift.

My advice for picking a good gift: I try to find something they wouldn’t think to get for themselves. It’s not really about what they “need” – it’s about giving them something special and unique. 

Leo Chan


I love the Mt. Hayes Buffalo Plaid Jacket because it’s warm and the pattern is perfect for the season, I would wear it for grabbing a coffee with a friend.

I need the Natick 17-liter felt Water-Resistant Backpack (similar here) because it’s water - resistant and I could use it on my regular commute to work - or traveling on my next adventure.

I like the Batson River Plaid Flannel Shirt because plaid shirts are such an essential item for the season. I would wear it lounging around at home or layer it under a sweater for when I head out into the elements.

I want the Dublin Beach Winter Beanie because when the temperature drops it’s important to keep your head warm. This beanie has a season ready pattern that stands out from the rest.

My favorite drink this season: Hot cocoa – you just can’t beat it.

My favorite food for this season: Apple pie served with a scoop of ice cream. Always hits the spot after a nice big meal.

My favorite book for this season: Harry Potter. I’ve watched the movies and visited the parks, so I’ll be digging into the books over the holidays.

My favorite winter activity: Feasting! No diets allowed at this time of year. And of course, spending time with family and friends.

The best gift I've ever received: An automatic watch from my girlfriend – it was exactly what I wanted and it will stay with me for a long time.

Our advice? This season, sip some hot chocolate, pop in Adele’s latest, read up on the wizard world, and get your holiday shopping inspiration with our Men’s Gift Guide and Women’s Gift Guide