Style Guide

This Is How You Crush It on Date Night, Sartorially Speaking

Seven key pieces to wear on Valentine’s Day and beyond (gifts not included)
Graphic: Jeremy Allen/Bloomberg; products: brands via Bloomberg

If prompted (by article writing), I can recall one of my more memorable Valentine’s Day dates for two reasons.

One: I broke the law.

I was 19, and my boyfriend at the time and I thought it would be super romantic to dine and dash at one of our favorite pizza joints* in celebration of our young love, or whatever. (Oh, adolescence!) Afterward, we drank a bottle of Boone’s Farm Fuzzy Navel with our feet in the sand, as we listened to the waves break on the Florida shore to a soundtrack of Dave Matthews Band and O.A.R. (See how I just editorialized my moment of crime to make it sound pseudo-romantic?)

And two: He wore pink.

A pink oxford shirt to be exact, which I believe was the only long-sleeve button-down shirt he owned. I remember it matched the sun-kissed skin on his nose and accentuated his toothy, expectations-laden grin (as well as the red-and-white checkered tablecloth and ruby red plastic tumblers of the pizza place).

Some 15 years (and 10 Valentine’s dates or so) later, I still remember that pink shirt. So take note, gents: What you wear come Feb. 14 does matter (at least in the immortalized memory of your current significant other).

Below, I rounded up seven no-fail wardrobe performers to keep in your date-night arsenal. V-Day may happen only once a year, but dressing to impress is a campaign you’ll want to continually crush.

*I’d like to take a moment to publicly apologize to the waitress at Stavro’s Pizza in New Smyrna Beach, who in 1999 witnessed me jump in the cab of a black Ford F-150 instead of paying, like a respectable undergrad, for my Greek salad and Diet Pepsi.

 The Slim Navy Peacoat


A well-fit peacoat is the definition of rugged elegance.

Source: MR PORTER via Bloomberg

What’s more handsome than you in this navy Burberry peacoat? (Hint: Not Rand Paul in his dad jeans.) $995;

The Check Suit

You want her checking you out.

For when you want them checking you out.

Source: Suitsupply via Bloomberg

This Havana gray check suit by Suitsupply is a heartbreaker (and I mean that in the most devastatingly awesome way). $569;

The Cream Cords


Corduroy: Dressier than denim, more casual than flannel trousers.

Source: Matches Fashion via Bloomberg

When the venue calls for a denim upgrade (free tip for Rand: That means a Koch brothers networking event), try a sand-colored corduroy pant—like this pair by Bottega Veneta. $490; 

The Pullover Cashmere Sweater


Who needs the distraction of buttons and zippers?

Source: MR PORTER via Bloomberg

Skin-on-skin contact is the only thing that feels better than cashmere, like this pullover knit by A.P.C. $250;

 The Knit Tie


Just add an unstructured blazer and a smile.

Source: Club Monaco via Bloomberg

A non-shiny chevron-print tie option, like this one from Club Monaco, is better suited for romance than it is for the boardroom. $79.50;

The Tan Brogue


Good shoes might not be the reason you get a kiss goodnight, but best to hedge your bets.

Source: East Dane via Bloomberg

Not to outshine your date, these buttery tan brogues by Grenson are certified ladykillers (by me). $405;

The Red Scarf


Pick a medium red hue that doesn’t underwhelm, but isn’t heart-shaped-box overkill, either.

Source: via Bloomberg

One piece of holiday-appropriate flair is enough, so keep it simple like this Gant wool fringe scarf in a red that’s reusable for other occassions. $64;

Nic Screws is the style director for Bloomberg. She is a cheap date (as outlined in the above memory). Follow her on Instagram and Twitter

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