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What To Wear When You’ve Got A Date After Work

February 13th, 2017

Tips for making a stylish day to night Valentine’s Day transition

In partnership with EliteSingles.

Since Valentine’s Day falls on a weekday this year, I thought I’d put together a look that you could wear to the office but that would also transition really easily if you happen to have a date after work. Here are some tips to help you dress to impress.

| PHOTOGRAPHY | by Rob McIver Photo | VIDEO | edited by Alex Harden

Stick to the basics. When it comes to the foundation of any outfit, I’m a firm believer that you can never go wrong with great basics. A classic navy blazer and a pair of charcoal grey pants, for example, are pieces that you can really do anything with. They’re infinitely versatile.


Patterns are less dressy. In situations where a navy blazer might feel a little too formal – if you want to be dressed up but not too dressed up – simply wear one with a pattern, like a subtle windowpane.


| WEARING | Ring Jacket coat, J.Crew blazer, Brunello Cuccinelli shirt, Banana Republic pants, Drake’s tie and pocket square, Shoes c/o Tommy Hilfiger

Try a denim shirt. Speaking of not wanting to be too dressy, one of my favorite ways to take a little bit of the formality out of a dressed up outfit is with a denim shirt. There’s just something really cool about a denim shirt paired with a blazer, tie and dress pants. It’s dressed up but has a casual ease to it, which is really chic and stylish.

Don’t wear bright red. You don’t have to, but if you are going to wear red on Valentine’s Day, stay away from big, bold and bright red colors. They’re just way too obvious. Instead, go with a deep burgundy or oxblood. It’s a little more subtle, it’s more subdued. Always remember that subtlety is one of the keys to being truly stylish.


Simple, versatile outerwear. Another key, especially in the wintertime, is outerwear. And again you can never go wrong if you stick to something classic. One of the things I really love about this navy coat is the subtle herringbone pattern it has. From a distance it looks like just a plain navy coat but as you get closer the details really start to reveal themselves.


While we’ve got you covered in the style department, there’s more to dating than just looking good. And since it is The Year of the Gentleman, we want to make sure you understand the finer points of dating.

It’s a little more than we can cover in the particular post, which is why we’ve partnered with EliteSingles to help you out with the art of conversation, body language, profile perfection and dating etiquette via their digital dating bootcamp.

Chime in: Besides looking your best, how do you put your best foot forward on a date?

Thanks, as always, for reading.

Stylishly Yours,

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers. Since 2013, his goal has remained the same: to provide men the advice and inspiration they need to dress well, develop their personal style, and gain more confidence. Brian’s interest and passion for men’s style and luxury watches has led to his writing for The Robb Report, The Rake, and Sotheby’s and he has been quoted on menswear in publications such as The New York Times, The Wall Street Journal,, Brides Magazine, and the Huffington Post. He lives in the woods north of Baltimore with his wife, Robin, kitties Nick and Nora, and German Shepherd/Collie mix Charlie.

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Videography by Rob McIver

Video Editing by Ian Johnston