Valentine’s Day is here, and we all know that this brings with it an unavoidable amount of stress. This holiday can bring up a lot of questions: like “What’s the perfect place for a romantic dinner?”, “Does my girlfriend/boyfriend even love me?”, and “Am I going to die alone?” Well I am not going to help you with any of those things, but I can give you some tips on looking your absolute best for however you choose to celebrate this evening.

If you’re going on a first date (bold move, may I add), this is a time to experiment a little. You don’t know each other that well, and probably don’t have a concrete understanding of each other’s personal “vibes.” Take a risk. Instead of choosing a candy apple red or an all-black ensemble, try maroon. Maybe add some lace, or engage in sparkle moment. I tend to often think high-heels are a bit overrated, but for a first date they can add a playful, flirty element. You want to have fun, and you also want to keep the conversation lively.  Wearing a statement necklace or carrying an eye-catching clutch can be used as a conversation starter. This would also be an opportune time to pop on a shimmery grey smokey-eye. It’s seductive and hypnotic, but also somehow still appropriate for “Cupid’s Birthday.” And if this person is a total and utter drab, at least you can pretend to cast a spell on them like some sort of mystic witch.

If you’re lucky enough to actually be in love, and actually dating someone who wants to fully participate in the occasion, I have just the look for you. You want to wear something chic and sophisticated, but also maybe something that carries a memory the two of you have shared together. It could be a cozy bomber you went apple picking in once, or maybe a classic dress you met each other’s parents in. Maybe even a pocket square you once used to help her wipe a single tear from her cheek when you met her in the Empire State Building elevator when you realised fate had worked it’s tricky hands in weaving your story together in, and out and in and out of each other’s lives.

But also keep it simple. I am assuming this person already really likes you, so there is no reason to put on a facade. Not that you should ever put on a facade, but in this case it probably really isn’t necessary. Or do put on a facade and see if they can still handle every side of your personality…the gift that keeps on giving. Now take a shot for every time I have said the word “facade.”

 

If you’re a single gal or guy, not looking to mingle, but celebrate with FRIENDS… then it’s time to pull out the blazers. Nothing says “I don’t need no man/woman” like confidently owning a sleek and well-tailored piece of casual office wear. Your friends love you, and they also want you to dress well for their party. But they love you, so love yourself as much as your friends do. When you’re with the ladies it’s fun to wear a red lip…cause the only thing those lips are kissing is the opening of a champagne bottle. Have fun, and remember there are so many things in life better than being in love. Like money.

And for the big event, some potentially very sexy activities might unfold during the evening. Lingerie is definitely an option. I would suggest all black, as red is a little to “been there, done that.” I would also suggest doing whatever the hell you want and whatever is best, and most comfortable for you. While it’s nice to have a day to celebrate loving others, and important to remember how lucky we all are to have certain people in our lives, celebrate yourself as well.

A reminder if Valentine’s Day rocks for you… congrats on living the dream.

A reminder if Valentine’s Day sucks for you… all bad things also have to come to an end.