Nailing Date Outfits for Men over 40
We've all been there.
Your date is in two hours, and you've been staring into your closet for 20 minutes, at a loss, feeling like nothing in the sea of clothes will be good enough.
Does the occasion call for a suit? A T-shirt? Or should you just call and cancel?
Should you wear the same old-favority first-date shirt again?
First-date styling doesn't have to be so stressful. With this comprehensive guide, we'll show you how to find the perfect attire for any date- without the fuss.
Step 1 To dressing for Dates: Assess the Date Venue
This client (above) came to us looking for date looks! Hear about his styling experience.
Sure, most dates are gonna be at a restaurant.
But hear me out: taking the venue into account is a huge part of setting the stage for a great date. Is it a bookstore, an upscale bar, or a downtown restaurant? Each setting may call for a slightly different ensemble.
Poise yourself for success by doing a little research into where you're going to prevent under or over-dressing.
What to look for when checking a venue for a date:
Browse photos in Google reviews. Is it dressier or trendier or more divey and laidback?
Consider the neighborhood. Do people dress a certain way where you're going?
Dress code. Is there a dress code for the restaurant, event, or location?
What is your date likely going to wear? If they tend to dress up more, maybe you should too.
What to Wear for A Bookstore or Museum Date
For a bookstore or museum date, "low-key pensive" is usually the right vibe to capture. Might as well lean into the whole professorial thing.
Try a simple, light-colored linen button-up with a sweater, because nothing screams intellectual like a good wool paired with trousers or nice jeans.
What to Wear for Grabbing Cocktails
For drinks, you can have the most fun playing with your look. Just make sure the look is elevated and sophisticated, depending on how dressy the venue is.
Go for a subtle bad-boy vibe with a leather jacket or cotton bomber over a pair of chinos or dark wash jeans and a fitted crewneck tee or turtleneck.
Dress it up or down with boots, loafers, or leather sneakers.
W Concept Cotton:On Ralph Lauren
What to Wear for A Dinner Date
The classic formula of a well-fitted button-up or polo, tailored trousers, and loafers is always a safe bet. The style of each item can be adjusted for your tastes and the weather, but this uniform always works.
It’s a look that exudes confidence, comfort, and sophistication without trying too hard but keeping your look modern. Opt for shirts in crisp cotton or soft linen in neutral tones or subtle pastels.
A flattering fit that’s neither too tight nor too loose is bound to please any date!
Step Two - Fit is Everything
No matter what ensemble you end up with, one of the most important factors in choosing a good date outfit for men in their 40s and 50s is fit.
Your clothes can help you exude confidence and class, by flattering your figure and complementing your features rather than fighting against them!
Tailoring might seem like a totally unnecessary part of the process, but it will make the world of a difference in your wardrobe.
Embrace your current body shape and work your closet with them rather than against them.
Step Three - Show Off Your Personality
The key to a good date is being authentic. Use your outfits to showcase who you are and what you're about!
This guide is meant to be an easy go-to for men who want to level up but aren't sure how to make sure they look good for dates.
It's easy to get caught up in what you think you "should" wear based on what you see others wearing, but style is about what feels right for you.
As a man over 40, you have a level of maturity and self-assurance that younger guys don't have yet. Use it to your advantage by embracing classic styles and higher-quality fabrics that age well and demonstrate your success--tastefully!
Don't waste time stressing about impressing your date with an outfit you think they want to see.
Instead, focus on making an effort in your appearance, and wearing what you genuinely like and feel good about.
Step Four - When in Doubt, Keep it Simple
When dressing for a date, it’s easy to fall into the trap of thinking you need to do the most just to be remembered.
Rather than stressing out or adding too much, the smartest thing you can do is wear what works and makes it easy to "wear the right thing".
Contrary to popular belief, good fashion is not about how many designer pieces you can layer or how many colors you can combine, it’s about creating a cohesive look that feels like you.
Step Five - Make The Effort
One of the biggest mistakes anyone can make (but especially men) is to assume it doesn't matter. A good shower or clean clothes is all it takes to be ready for a date.
It's not.
Do whatever thing that the majority do not do and you will stand out. When it comes to dressing for dates, that's making the extra effort. That means: steaming your shirt, shaving a five o'clock shadow, and hiring a stylist to give you the ultimate date wardrobe.
Step 6 - Use Your Age to Your Advantage
Besides having more money and experience, being over forty gives you an edge that younger men don't have.
You know what you're doing in a way that someone twenty years younger doesn't. Plan, make the reservation, book the car, and pay before your date can see the bill.
Alright, Let's Wrap Up The Final Bits On Date Looks for Men Over 40
Remember, style is an extension of who you are, and the best look always lets your personality shine through— whether that’s a classic blazer, a great pair of jeans, or a stylish, well-fitted shirt. The key is to opt for items that align with who you are and make you feel like the best version of yourself.
That confidence isn’t about being the loudest or most outgoing in the room; it’s about being comfortable with who you are!
So, next time you prepare for that date, take a deep breath, keep it simple, and trust yourself.
