Casual Valentine’s Day Date: No Red Necessary

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A casual Valentine's Day date is the perfect time to break out the wingtip leather dress boots.

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You know how we feel about the turtleneck in place of the button up shirt (i.e. the sartorial power substitution).

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With a relatively simple outfit, always add a great accessory like a silk scarf.

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And top the look off with a killer coat.

A casually sophisticated Valentine’s Day outfit idea sans the “obligatory” red

If you’ve got a Valentine’s Day date coming up next, you want to look your best. That’s obvious But looking good doesn’t mean having to wear a suit and a tie.

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

In fact, if it’s a more casual date or a date with someone you’re just starting to get to know, not going overboard is very important to making a good impression. Today, we’re showing you one way to dress casually, but still look put together this Valentine’s Day.


One of the things I don’t really like about Valentine’s Day in terms of choosing what to wear is this idea that you need to wear some kind of red. For me, wearing red on Valentine’s Day is a just little too obvious and can easily make you look like you’re trying too hard. Instead, try out some dark colors, like a deep navy. It’s cool and really gives off a confident and put together vibe.


| WEARING | Daniele Alessandrini coat, Uniqlo turtleneck, J.Crew jeans, Drake’s scarf, Rolex watch, Boots c/o Allen Edmonds

Regular HSS readers know that I’m a big turtleneck guy. A turtleneck is a great substitute for a button-up or crew neck sweater. It’s elegant, it’s got a relaxed sophistication but it’s still casual at the same time, especially if you’re pairing it with dark denim.

Now if you keep the rest of your outfit relatively simple, it’s always good to add in some type of accessory. And for me nothing is better than a lightweight silk scarf. The one that I’m wearing is by Drake’s and I like it because it’s relatively short which means it’s easy to wear just as a simple accent with a sweater or even under a blazer.


Finally, you’ve got to anchor your look with great footwear. A pair of wingtip leather dress boots, like the Dalton that I’m wearing here from Allen Edmonds, is your go-to pair of boots for a casual date look like this.


And tell us, how about the video OOTD? Like? Dislike? Want to see more? Chime in below!

Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style


Chime In

  • Paul McCool

    Love the video, Brian! It’s good to put a voice to a face. That coat is great with jeans.
    I personally have never wore red anything, not even a tie!
    Keep up the good work and advice.

    • Brian Sacawa

      Glad to hear that, Paul. We’ll be doing more in the future and hopefully improving the product as we go!

  • Filip

    What is the model/name of this coat? Couldn’t find it.

    • Brian Sacawa

      It’s by Daniele Alessandrini. A couple seasons ago so no longer available. Outfit details are always listed in the post.

      • Filip

        That it is from Daniele Alessandrini I noticed :). If it’s not from this season it explains why I couldn’t find that particular one… Thanks for reply!

  • Jo

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  • Khoi N.

    Always love the production quality and succinctness of your posts. Keep up the great content!