First dates can be intimidating. You want to give off a stellar first impression based on your style and good looks, but you also want to make sure your date gets the right message—you’re cool, confident, and as suave as they come. If you’re the type of guy who waits until the absolute last minute to figure out an outfit appropriate for the date you’ve scheduled, it’s about time you broke the habit.

Pick the Perfect Look for a First Date

Though it may seem that men have it easier than women when it comes to first date wardrobe selections, men still have plenty of trial and error to go through before truly nailing the right fit. That first impression is everything, and if you arrive in an outfit that flops, you’d better hope your date is able to look past it!

We’re here to guide you through how to pick the perfect look for a first date, giving you the lowdown on the items you’ll need to wow your date into a second, and third date.

Tip #1: Pay attention to details

Believe it or not, sometimes it’s the smallest things that make the biggest impression, so it’s well worth your while to focus on the little details before piecing together the full ensemble. Whether that means ironing out every last wrinkle on your shirt or opting for that special occasion gold watch instead of your everyday smartwatch, pay attention to those little things that make a world of difference in your appearance.

Tip #2: Stay true to your taste

The last thing you want to be while on a first date is uncomfortable. Whether that means skipping the infamous too-tight shirt or saving your experimental funky-patterned shoes for a more appropriate evening, staying true to your taste means choosing comfortability. Think of it this way: you want your date to get a solid idea of the man you are—pretending to be someone you’re not or forcing yourself into a pair of pants that just don’t fit is not the way to go.

Tip #3: Find some style inspiration

Stumped trying to figure out how to dress for your first date? Rather than scratching your head or panicking, surf the web or scroll through your Instagram feed to find a few looks that could serve as inspiration for your night on the town.

Not sure where to begin? Check out these male models with fantastic style to get the ball rolling:

Tip #4: Dress for the occasion

Maybe you’re headed to a casual coffee date, or maybe you’ve planned an extravagant night on the town—whatever you have in store for you and your date, making sure you’re dressed the part is a key piece of the puzzle. Much like reading the room in a new setting, understanding the dress code for the event on your agenda is essential.

Tip #5: Run your outfit through our do’s and don’ts


  • Match your belt with your shoes
  • Know how to properly tie a tie
  • Wear a watch
  • Embrace neutral, minimalist colors
  • Know your measurements
  • Hydrate and moisturize your skin
  • Wear cologne


  • Opt for shorts when it’s below 50 degrees
  • Be afraid to express yourself
  • Wear open-toed shoes
  • Forget to clean up your facial hair

Tip #6: Pick from the essentials

Pick The Essentials

Depending on your style, your everyday clothing essentials may not be up to par with what your date night essentials should look like. Crafting chic outfits that are equal parts tasteful and expressive is made simple when you’ve got a strong inventory of staples that pair well with just about anything.


  • Button-down dress shirt
  • Tailored blazer
  • Bomber jacket
  • Crewneck sweater
  • Collared tee
  • Denim chambray


  • Dark wash jeans
  • Black jeans
  • Chinos


  • Oxfords
  • Chelsea boots
  • Chukkas
  • Casual sneakers


  • Belt
  • Watch
  • Sunglasses (when appropriate)
  • Wallet


No more scratching your head in front of your closet minutes before your date, and no more failed first impressions! While there is no right or wrong answer to figuring out how to pick the perfect outfit for a first date, there are plenty of tips and tricks to keep in mind when piecing it all together.

Read Also: Looking to go on a summer date with your loved one? Check out our guide on “Date Ideas for a Summer Adventure.

Shield Yourself Now

Lewis Gordon is a successful businessman living in Boston, Massachusetts. When he’s not working, he enjoys travelling – especially tasting other cuisines, scuba diving, watching and playing soccer. Lewis also has a love of dogs and is the proud owner of an English Setter.

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