Help Me Dress Myself: Turning Work Clothes Into Party Clothes

A stylist explains how to put together an outfit that's appropriate for both a day on the job and the holiday party you’re headed to afterwards.

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Are you one of those guys who wants to look stylish but finds it doesn’t come all that naturally? We feel you. Don’t fret: With some advice from LA-based stylist Meg Gallagher, we’re all going to learn how to dress a little better. In this edition, we’ll be putting together outfits that are appropriate for both a day at the office and the Christmas party you’re headed to afterwards.

Outfit #1: Formal to Business Casual

If you have to wear a suit and tie to work but are headed to a Christmas party at your favorite dive bar afterwards, Gallagher says swapping out your blazer for something with less structure will loosen up any outfit. “Take off the tie and replace your blazer with either a knit sweater or a chunky cardigan. As a rule of thumb, knits make every outfit more casual across the board.” While we know it’s tempting to pull out your favorite Christmas sweater for this occasion, know that the fashion police say it’s best to save it for the inevitable ugly Christmas sweater party.

Outfit #2: Casual to Business Casual

If you work in a casual environment but want to look a little more dressed up for your post-work holiday party, Gallagher says the key to your outfit is a jacket. “Wear jeans and a patterned button-down to work, but bring either a blazer or a bomber jacket to put on afterwards. When you’re headed to the party, roll down the sleeves and put on the jacket.” Now you’re dressed to impress without sacrificing comfort during your day on the job.

Outfit #3: Professional to Formal

If your work generally requires a suit anyway, but you have a formal holiday party to attend afterwards, Gallagher suggests adding accessories to spice up your look. “Wear a dark-colored suit [navy, charcoal or black] with a white button-down shirt to work, and bring both a tie and a pocket square to put on afterwards.” Or, if you’re feeling festive, Gallagher says wearing a bow tie is the way to go—just don’t get too crazy with it.

If you have any questions about getting the look you want—fits, cuts, colors or anything else fashion-related—email us at bm@dollarshaveclub.com. We’ll have Meg answer it in an upcoming post.