What to Wear on a Valentine’s Day Date

Let me help you with your Valentine’s Day checklist. Have you gotten her something she’s going to love? Made a dinner reservation? Or at least picked a place for drinks? Set a reminder to buy flowers? (Don’t forget mom!) Thought about what to wear?

If the answer to that last question is “no,” don’t worry – we’ve got your back.

Here are a few outfit ideas from the HSS Style Guide that will have you covered whether you’re planning something low-key and casual or elegant and highly romantic.

1. She’s The One

You’ve got to go all-out if you know she’s the one, but don’t confuse all-out with overdoing it. To me, all-out is one of your best, polished and classic outfits. And don’t worry, she’ll notice the wingtip dress boots after you give her that bouquet of flowers.

2. Solid Basics

Don’t neglect the basics like slim dark denim and a navy blazer just because it’s a special occasion. Dress them up while still keeping it rugged with a chambray shirt, hearty tie and contrasting scarf. Perfect for a first, second, or third date.

3. Understated Elegance

If your Valentine’s Day plans include dinner at a nice restaurant, swap the shirt and tie in favor of a turtleneck. Every dude’s going to be wearing a shirt and tie so why not stand out in a sophisticated and elegant way?

4. Low-Key Early Evening

Don’t forget about white denim. For a Valentine’s Day brunch date that may or may not transition to late-afternoon/early-evening drinks, it’s a perfect, more polished option that regular blue jeans.

5. High/Low Comfort

Have a date with a long-time flame? Try going high/low. Tone down a dressed up look – classic trousers, button-down and double monks – with a casual and versatile menswear staple like an athletic sweatshirt.

6. Casually Tailored

When in doubt, combine some of your favorite casual basics with tailored pieces in your closet. A waistcoat does an amazing job of taking an okay outfit to a different level.

7. After Work

Hey, maybe you have to work on Sunday! Even if you don’t, a smart office look can easily double as a well-put together Valentine’s Day date night outfit. No hints of red? No problem. A color does not a festive mood make.

8. Night On The Town

If you’ve done the requisite research into the optimal number of pairs of jeans you should own, you might be trying to find a way to work in your “in-between” dress pant into the mix. If your night is going to be a late one at a swanky lounge, go for something darker and edgier. It’ll be a little cold so accent the monochrome with a scarf.

Now that you’ve got some outfit ideas, take our resident Italian guy’s refresher class on how to charm a woman.

Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style

Photography by Rob McIver Photo