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Blog Mr. Big & Tall

What to Wear on a First Date | Tackling That First Date Outfit


What to Wear on a First Date | Clothes for big and tall men

4 Tricks To Tackling That First Date Outfit 

Congratulations, you’re going on your first date with that person you’ve been crushing on for a while.  

And you have our sympathies, because you must be fretting about what you’re going to wear. We get it. We’ve all been there.  

Self-conciousness with clothing options is a natural state for us big and tall guys, but especially so right before The Big Date. The goal as always is to narrow down your options with four easy rules. Follow, narrow and decide so you can be sure you can focus on your date partner and not how you look throughout the night.  

The Rule of Shoes (and a jacket)  

Your date will absolutely notice your shoes at least once. So make sure they’re clean (invest in some wipes) and tied.  Depending on the date location you may opt for leather or something more casual. Just no Nike sneakers unless you’re already unsure about your date and are preparing for a quick getaway.  

And wear a nice jacket, guys. Nothing branded or too bulky.  

The Rule of the Bar 

Ah, yes. The bar date! Super-laid back. Good energy. A fun time.  

In that vein, go simple! A white tee with a simple jacket over it will make you the class of the bar. If you wear jeans (as you should for this location) settle for something less baggy and darker-hued. The darker colors down low will keep your date’s focus on your wonderful face and keep you both engaged in conversation over drinks.  

The Rule of the Restaurant 

Now we’re getting more complex. A dinner date requires a bit more thought. You’ll need to pick an outfit for a few steps of the process: picking your date up or arriving to the restaurant and what you’ll be wearing throughout the dinner.  

Odds are you’ll need a jacket for the arrival, and this is where bomber jackets come in handy. They aren’t so bulky that you’ll feel removed from your date, but they’ll be stylish and warm enough they might even ask you for it if it gets too cold. The movie dream!  

And, unzipped, it provides a nice sneak preview at your actual dinner date outfit: a nice long-sleeve complimented with smart pants and black or brown shoes. Remember the classic long-sleeve tips for big and tall men, though: nothing too vertical for tall guys and not too many layers for bigger guys. Everything needs to be simple about your first date outfits, so you’re not worried about feeling comfortable and your date isn’t overwhelmed by your clothes.  

The Rule of Fun 

Ah, now you’re spending hours on your first date? Well, you’ll need something that transitions well from activity to activity and from day to night. Hey, you were the one who suggested this.  

As ever, the lighter the better. Unless you sweat deodorant, you need to wear light colors and fabrics for your activity first date. That means casual pants and a light crew-neck. When dusk settles, make sure you’ve stowed a mid-length coat away in your car for that walk to dinner.