The holidays, while enjoyably festive, can at times feel like a burden. Your calendar fills up for nearly three months with activities. It might mean a fair amount of uncomfortable chit-chat with colleagues after a few cocktails, perfecting your place settings to entertain your family for the afternoon or creating the perfect ambiance for a gift exchange with your significant other. It’s a lot. It can be stressful. And you really don’t want to wear the same outfit for every event, do you? To eliminate some of the potential fretting, we’ve put together a few looks, paired with some of our favorite Timex watches, for inspiration to get you through any occasion.

The Annual Office Party

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Your annual holiday work party: it’s an occasion to get to know that guy who sits across the office from you, finally connect with your boss’s boss, maybe even cut some rug. Just be sure to keep your booze intake to a fair minimum (you’d have a whole year to live it down) and use it as an opportunity to look extra sharp. Upgrading black denim with a classic cashmere turtleneck and slim checked blazer, dotted black socks and some premium leather sneakers from Koio is the way we’d go. We paired it with the Timex Waterbury Classic; it’s clean and timeless and the warm leather strap and steel case add to the effortless quality of this look.

The Waterbury Classic by Timex $99
Grey Slim Fit Blazer by Officine Generale $695
Slim-Fit Merino Wool Sweater by Officine Generale $275
1960 606 Slim Fit Jeans by Levi’s Vintage Clothing $225
Dotted Cotton-Blend Socks by Barneys $45
Capri Nero: by Koio $248

The Family Dinner

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Whether you’re a tight-knit crew or less than, hosting your family can be taxing. Is your bathroom clean enough? Did you remember everyone’s dietary preferences? Is the wine up to your dad’s standards? You have to prepare the dishes, set the table, light the candles — and do it all without breaking a sweat. There really isn’t time to stress over what to wear on top of it. Rather than go fully festive in a red and white pullover, we paired an indigo-dyed button down with navy chinos and a pair of black and white leather lace-ups. Timex’s Weekender Chronograph, with its navy face, is what we’d add to this look. It’s the perfect mix of polished and casual, plus you’ll really want to keep an eye on the clock ahead of entertaining.

Weekender Chrono Oversized: by Timex $82
Japanese Dot Shirt by Corridor $195
Connor Chinos by Club Monaco $99
Classic Crew Socks by Vans $22
OG Leather Old Skool LX by Vans $100

The At-Home Gift Exchange

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Just because you’re staying home doesn’t mean you need to completely let go. You have to keep the spark alive. After you do your last minute wrapping, a simple but elevated cashmere sweater and wool drawstring pants will do the trick. You won’t look like you’re trying too hard, but you will look like you care. Yes, you can just wear your socks, but maybe pick your best pair (a pattern goes a long way). The Timex Fairfield Chronograph is our watch of choice here, a Bauhaus-inspired, multi-functional chrono. The minimalist quality and perforated leather band are a solid complement to elevated at-home attire.

Fairfield Chronograph by Timex $99
Cashmere T-shirt Sweater by Todd Snyder $268
Cashmere Flannel Drawstring Trouser by Sunspel $245
Polka Dot Socks: by Paul Smith $30

For Her: Fairfield Women’s Crystal by Timex $89


About the Location

This look was shot at Sixty Soho’s newly redesigned, bi-level Sixty Loft Suite in New York City.
Learn More: Here