Valentine’s Day Outfit Inspiration

Well, the romantic day is almost here. You’ve got her gifts picked out. Her flowers are ordered. You have everything you need ready to go. But what about you? Are you ready? Do you have your Valentine’s Day outfit picked out yet? In our focus to make Valentine’s Day as special as we can for out partners, we sometimes neglect ourselves. I know I have been guilty many times in the past of forgetting to take care of myself. So, I thought it might be a good idea to get a head start on some Valentine’s Day outfit ideas for both casual and dressy dates.

I can already hear the chuckling from here. “Do guys really plan their outfits beforehand?” I do. Sometimes. When I want the night to be memorable. Does that mean I have everything laid out for two weeks sealed in a hermetic enclosure? No. Nevertheless, I definitely have an plan of what I am going to wear.

I worked in the restaurant industry for years, and Valentine’s Day was always insane. To me the only day crazier was Mother’s Day. I still have flashbacks about Mother’s Days from the past. Seriously, if you go to a restaurant on one of those busy days: Mother’s Day, Valentine’s Day, New Year’s Eve, Easter Sunday, etc. be nice to the staff. Chances are they’ve been there for hours before they opened, and they’ll be there for hours after they close. A little kindness goes an extra long way those day. Ok, mini-rant over. I bring up the restaurant days because I saw a lot of couples come in for romantic dinners over the years, and I think I had a unique vantage point as observer.

I had two main takeaways from that time. One, let your date shine. Subtlty is king. Nothing will let her feel more important than you letting her take center stage. I believe that on any important romantic day we, as men, are the accessory to her beauty. Don’t steal her limelight. Two, go easy on the red. Yes, I know it’s Valentine’s Day, and this is your special Valentine’s Day Outfit, but with a bold color like red, I think less is more. I can’t tell you how many times I saw the satin red shirt with a black tie combination. It looks terrible. Leave the red for the accessories like a pocket square or a lapel pin. I prefer softer colors like pink for larger pieces like shirts and ties.

As inspiration today, I pulled together two Valentine’s Day outfits, one casual and the other a more formal option. I’d love to hear your thoughts on these outfits. Leave a comment below!

Casual Valentine’s Day Outfit

Casual Valentines Day Outfit
Casual Valentines Day Outfit

Jeans: AG Jeans  //  Shirt: Brooks Brothers  //  Jacket: Ralph Lauren

Tie: The Tie Bar  //  Shoes: Allen Edmonds  //  Socks: Paul Smith

Tie Bar: Ox and Bull Trading Co.  //  Underwear: Mack Weldon  //  Belt: Club Monaco

Dressy Valentine’s Day Outfit

Dressy Valentines Day Outfit
Dressy Valentines Day Outfit

Trousers: Santorelli  //  Shirt: Saks Fifth Avenue  //  Jacket: Hart Schaffner Marx

Tie: Barneys New York  //  Shoes: Allen Edmonds  //  Socks: Pantherella

Pocket Square: Nordstrom Men’s Shop  //  Underwear: Mack Weldon  //  Belt: Allen Edmonds