Valentine’s Date Scenario III: His House for Dinner

If you’ve been following our Valentine’s Day Style Guide series, then you know how much fun we’ve been having challenging our friends over at Tog + Porter to come up with outfits for different Valentine’s Day date scenarios. We’ve done classic romance with my ‘Over the Moon for You,’ date. Then we did something a little more out of the box for a newly dating couple called ‘Adventurous and Quirky’. Now it’s on to the third and last date, ‘An Invitation to His House for Dinner’. What makes this date especially interesting is the couple’s dating history. The gals over at Tog + Porter actually have a name for this date; they call it the “Determining The Relationship” or “DTR” date.

Here’s the details I gave them about the couple and how the night would unfold:

This couple has had 5 dates and always very fun and “PG.” He’s been the consummate gentleman but after consulting with his buddies felt he needed to see if that serious romantic *spark* was there. He’s into her but they definitely haven’t had an exclusive chat yet. She feels like he is a total diamond in the rough and she is seriously liking him.

He sends her an email to come over to his home for a Valentine’s dinner. She’s never been to his house and a homemade dinner sort of makes her sweat. It feels really “real” and “serious.” The dates so far have been easy going and fun. Lots of laughter, affection, and chivalry. She feels butterflies thinking about this date because she knows it could lead to something more serious.

She emails him back and accepts the sweet invite asking if she can bring anything. He says, “Nothing…only you.”DTR Date

The day of, she heads to her liquor shop and gets an incredible cognac to share. She also brings him an Hermes tie with little puppies on it wrapped up beautifully. He just got a rescue pup, so she thought this would be a cute way to acknowledge this and thank him for a lovely evening.

He’s gone far to impress her. Rose petals on the floor in the entryway, champers to start with, steaks and veggies he grilled, and chocolate chip cookies they baked together.

She stays the night and wakes up in the morning to piping hot coffee and the smell of his cologne lingering on her. She’s doesn’t want to leave.

Now for the big question: What to Wear? Here’s what I told T+P stylist Maureen about the couple’s style:

He’s more of a buttoned up type (successful career in finance) and opts for the preppy look on the weekends. Being from the East Coast, she is definitely more Kate Middleton than “The Olsen Twins” in her style and she’s pretty conservative in general.

As she thinks about this date, the more she realizes she doesn’t want to be stuffy. Instead, she wants to look sexy but not trying too hard. In other words, it is about bumping up her sex appeal a few notches.

Maureen knew exactly where to take it from here. “She needs to show him she’s into him, serious and ready to move forward,” she said. “She wants to look and feel sexy and her look should be suggestive, but not too inviting. She should also bring an element of comfort to her chic so she looks relaxed in his home.” While my client might be resistant to this outfit at first, the ladies at T+P say they’d encourage her to push the envelope a little and give something new a try. I agree it’s the furthest thing from stuffy and she’ll undoubtedly knock his socks off once the jacket comes off.DTR Option 1

She should feel her absolute best and allow her outfit to emulate her mood and draw even more attention from him than she’s already garnered,” said Maureen. I couldn’t agree more and I think this is a mission accomplished! This second outfit is feminine and flirty (both good), but just the right amount of edge thrown in to keep it interesting. DTR 2

Maureen also added a slightly less inconspicuous overnight satchel bag.

Have an important date coming up? Let the stylists at Tog + Porter help you accomplish your style goals and put your best foot forward. If you still need help with your Valentine’s Day outfit, be sure and sign up for a style consult ASAP, time is running out.