What to Wear for Valentine’s Day Part I: The First Date

Valentine’s Day is this week! It’s that time of year where you pull out all the stops, dress yourself to the Nine’s, and ask that gal you’ve been eyeing in class on a Valentine’s date. Now hopefully she will have said yes, so what are you supposed to wear? What does the occasion call for? Are you going to the beach, having a picnic at the park, or taking her out to a swanky restaurant? Fear not confused gentleman, we have a guide just for you.

For this Valentine’s Day we have asked several of our well-groomed friends what they would wear to their date. We have three different situations based on different occasions to go off of: The First Date, The Girlfriend, and The Fancy. 

Today’s post will be about the First Date. We also asked each them what their ideal first date is, so listen up ladies. 😉

(Except Tim. Tim’s taken lol)

1. The “Clean and Simple” on Christian


“My thoughts on my outfit would be that you would want to be just as comfortable in the clothes you’re wearing,as you are with the person you’re going on a date with, but you would want to put on something a little more classy to make a better impression for your date. Something that isn’t being a try hard, but is showing that you put thought and care into your presentation” says Christian. “I feel that my outfit shows that you’re dressed well enough to go to a semi-fancy restaurant while at the same time being able to do fun activities like a movie or ice skating.”




Shirt from H&M, Pants from Express, Shoes from Footlocker

2. The “Easy like Sunday Morning” on Ian


“For my first date outfit, I didn’t want to come off to strong. I want to be comfortable and wear something that reflects the environment of where the date would be.”

For my first date, I would do something simple and clean just to break that “first date” barrier and get to know the girl a little more, to bring her into my world a little. Something social, like the art museum, or something in that area, then grab a bite to eat and take a walk around the city.The outfit works with this because it fits the environment. Not to upscale and not to casual.”




 Long-Sleeve Shirt from H&M, Undershirt from Forever 21, Pants from J Crew, Shoes from Sperry’s

3. The “Brunch at Berkeley” on Rajesh


“An outfit to fit this experience is one that is comfortable, looks good, and reflects who you are. That’s why I chose a comfortable and well-fitted khaki trousers, a nice cotton oxford with a subtle vertical stripe pattern. To help keep warm and add dynamic texture, I added the vest. The shoes are simple and comfortable loafers.”
“I personally enjoy the experience of eating at a restaurant. It isn’t just the food, but the conversations that spark around food. Not only that, the after meal coffee or tea is where I have had some of the best conversations of my life. Ideally the great first date in my opinion is to take her to a restaurant that is unique, simple and with fantastic food. We’d talk over the meal. After our meal we’d sip our tea/coffee to which we learn more about each other with the excitement of wanting to know more about each other.”




Shirt from  J Crew, Pants from J Crew, shoes from Nordstrom, accessories from Taylormade and Watch

4. The “Downtown Lumberjack” on Tim


“On my first date I want to be wearing my “go-to” gear. My “go-to’s” consist of my favorite articles of clothing that I know fit well and look good on me. I don’t want to be self-conscious about any aspect of myself when I’m on a date. I want to exude nothing but confidence. This way the outfit will come off as effortless, and I’ll still be comfortable.”

“I’d like to start my first date out at a nice cafe and have lunch while we talk and get to know each other more. After that I’d take her to a nice park or the beach so we can walk around and explore, after which we could catch the sunset. For me the best part of first dates are the conversations; getting to learn more about this new person that you are with. I think the beach or the park are great calm and romantic places that allow conversations to flow easily.”




Short-Sleeve Button Up from Topman, Jeans from Pacsun, Shoes from Clarks, Socks from Penguin, Accessories from Misc. 

5. The “Biker Nerd” on Ethan

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“I feel that you should be able to look like yourself on your first date, without being too fancy.  I mean, I like wearing ties and people think that ties are too fancy to be worn casually.  This outfit was kinda made to prove that ties can be fun and dressed down.   The amount of patterns and print work together in my unique way, and they also make the outfit modern and hip so I can show my date that I can have fun with my outfits.

I’d personally use this outfit for any night in the city, getting food, walking around, just being casual.  It’s a diverse outfit that can look good in any first-date occasion, casual or semi-formal.  I wouldn’t recommend going too formal because…well it’s a first date!”


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“Always wear a jacket and a sweater on your first date.

That way, you can give her your jacket and still keep warm if it gets cold!”

Jacket from Ebay, Sweater and Shirt from H&M, Tie from thrift store, Boots from Nordstrom

Which was your favorite outfit? Would you wear any of these? We hope that you’ve gotten some inspiration for what you’d like to wear for your first Valentine’s date with your lucky girl or guy!


Tim M. (P.S. – this is the first post I’ve written so far HA YES I AM A PART OF THIS BLOG.)

Street x Sprezza

Photography by Ethan and Tim

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