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First-Date Fashion for Men

It’s your first date and you want to everything to be perfect. You’ve picked out the right place to go and have decided which flowers to pick up on the way over. You’ve had your hair cut last week and now it’s time to decide what to wear. The key to dressing fashionably is to take you and tweak it a bit to maximize your style.

First-Date Fashion for Men
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It’s your first date and you want to everything to be perfect. You’ve picked out the right place to go and have decided which flowers to pick up on the way over. You’ve had your hair cut last week and now it’s time to decide what to wear.

The key to dressing fashionably is to take you and tweak it a bit to maximize your style. No matter where you’re headed, the key to looking great is to dress for the occasion while preserving who you are at the core. Here’s how to put together the right pieces for right kind of look you want to go for.

The Hipster (City)

Not quite old-school, not quite metropolitan and best of all, designed with a minimalist concept.  The hipster in the city is a fusion of new and old for a look that's smooth and intellectual yet casual and easy-going.

Go Classic: Start with the basics as your foundation. Try a fitted collared shirt and pair with straight leg jeans or flat-front trousers. Just a simple addition of a jacket or sweater can add depth to your outfit.

Trend Alert:
Straight leg pants are today’s most popular fit. If you need more room, try pants that are slightly slouchy but not baggy. This same notion applies to tops. Avoid wearing shirts that are too tight or too revealing. Opt for just fitted. Keep it classic and stick with conservative colors like solid blacks, whites, grays, browns or beiges.

For a more casual style, leave your collared shirt untucked and cuff sleeves to a 3/4 length. For an added flair, layer a cotton sports jacket on top. Quick Tip: Keep the length of your shirt even with the hips if wearing un-tucked. 


Go Trendy: Generally, it’s a good rule of thumb to veer towards simplicity on the first date. You want to blend classic pieces so that you look nicely put together but not go over-the-top so that your outfit distracts from you.

Escape a fashion no-no by picking just one piece of your outfit to accentuate. It can be anything from your shoes, sweater, or jacket. Keeping minimal in mind, here are some examples of how you can combine your basics with some of today's new styles.


Outerwear Top Bottom Shoes
Brown Houndsooth Blazer Tan solid button-up Denim fitted jeans Brown lace-ups or loafers
Argyled or striped sweater , say in black/gray Gray polo (match undershirt with one of the colors in the sweater) Flat front trousers Black lace-ups or loafers
  Oxford with military inspired detailing i.e. chest flap pockets or epaulettes Denim fitted jeans Brown lace-ups or loafers
Navy cotton blazer Light blue tee or v-neck sweater Denim fitted jeans White canvas sneakers

Where This Works:
  • Happy hour
  • casual dinner
  • casual party
  • a night out in town

 

The Black Tie (Formal)

You have to suit up for the occasion but it doesn't mean you have to dust off the three-piece. How do you command a look that’s refined but not stuffy, classic yet modern, and structured but comfortable?

Go Classic: First, begin with the basics. You may think the traditional black suit and classic white dress shirt is too easy but there is an absolute style in classicism. Because it’s not too distracting or overdone, it just quietly exudes sophistication.

Here are some ways to dress up the black suit:

–Boldly striped ties –Satin ties (try metallic silver, pink or purple) –Black calfskin leather belt with silver hardware –Silver cufflinks or studs –Satin pocket handkerchief for an old   Hollywood flair –Black patent leather lace-ups designed with    a narrow toe box
Quick Tip: Shoes can carry as much weight as an expensive wristwatch, so at the very least, they should be clean and polished.
Go Trendy: Mix up your suit outfit. Instead of "that jacket" that goes with "those pants," you can swap your jacket with one of three options:
  • A blazer of a different texture i.e. a luxurious velvet
  • A waistcoat
  • A thin sweater over your button-down

To celebrate summer, opt for a lightweight cotton suit in light beige or ivory.

If you’re looking to substitute your traditional white dress shirt, try a solid pink, midnight blue or royal purple. Try to avoid neon colors or metallic sheens which can deter from the rest of your outfit. When in doubt, your safe bet is to contrast dark and light hues.

Quick Tip: When looking for the right dress shirt, it’s important to get measured for fit. You want the shirt to fit properly at the neck and sleeves and tailored correctly so that it eliminates the billow and fits snugly against your body.

For your bottom, pinstripes lining the vertical of your pants can do masterful job of creating a look that’s ultra sophisticated.

Where this works:
  • Romantic dinner
  • Theater

 

The Varsity (Casual)

The style is laid-back. You can leave your more experienced clothes in the drawer, say your favorite jeans or T-shirt and still feel as comfortable as you look. Here’s how you can gear up fashionably for a casual day out.

Go Classic: When you're in the stands, play with a brightly colored polo or a pocketed basic T-shirt. Quick Tip: If possible, opt for a plain top, one that's void of any flashy lettering or logo.

Layer a long-sleeve tee underneath if the weather is mild. Hide your head beneath a zippered hooded top for that hot day turned cool night. Indulge in soft and lightweight materials like cashmere and merino. Quick Tip: The zippered top is functional yet fashionable because you can layer but take on or take off with ease.

Match with chino or linen shorts. Or try a faded denim jean in both color and density.

Go Trendy:
When you’re on the green, you can match your pique polo shirt with a pair of plaid or seersucker shorts. Trend alert:
White is clean and crisp for summer. You have your simple white shirt varieties in crew, collar, or v-neck or white shorts in chino or linen.

A weathered button down in stripes or plaid can add another dimension to your outfit. Try bold yellow and blues or greens and oranges.

Make it snappy and wear a sweater vest over your T-shirt or polo.

On your feet:

Where this works:

  • Museum
  • Walk in the park
  • Coffee

 

The Pro (Athletic)
For clothes befitting a day outdoors, the look is in the make. You want to be able to bend, stretch, jump and play in a get-up that not only looks hot but can also take the heat.

Go Classic: For an athletic first date, opt for a style that’s constructed but not constrained. It’s important to wear breathable materials like cotton or nylon.  Match a plain basic T-shirt or polo with cargo shorts. If cargo is too heavy, opt for a pair of nylon shorts. A cotton-hooded sweatshirt or track jacket is perfect for when the sun goes down. If hitting the waves, consider board shorts decorated in camouflage or a fun Hawaiian motif.

Go Trendy:
With this look, you can be more liberal in your color choice. Work from a palette of solid colors for a look that’s clean and crisp. For a daring but summery celebration, try a bold yellow or orange.

Quick Tip: Remember learning complementary colors in art class? Use a color wheel as a general rule of thumb. Combinations using colors directly opposite each other or next to each other work well together.


On Your Feet:
  • Sneakers appropriate for the activity
  • Rubber slide sandals or thong sandals
Quick Tip: Reserve a pair of sneakers for casual outings and a pair of sneakers for your daily workout.

Where this works:

  • Hiking
  • Sporting event
  • Beach

Check out First-Date Fashion for Women >>
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163 comments on “First-Date Fashion for Men


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1008Chris wrote:
I consider myself to be rather stylish, and none of the pictured looks really impressed me. You want to dress for the occasion but yet make a good impression on your date. Remember that your first impression is the most lasting one. What ever you wear, you want to be comfortable, don't lose your identity trying to impress someone else. I personally love jeans, because you can dress them up with a nice button down shirt and a blazer, or you can dress them down with a simple polo shirt.
I LOVE jeans with a blazer. Excellent choice.

Posts: 9

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Please be yourself, clean and tidy, comfortable, no stuffed shirt, but presentable. For heavens sake whatever you do, when meeting the girl for the first time, Don't wear something bizzarre to stick out in a crowd.......she may walk right past out of embarrassment. I'm an older gal, prefer clean, nice smeliing, be yourself kinda guy. I figure at this point if you don't know what to wear, there are probably bigger issues at play. I would hope by the time you have gotten to the date phase you know enough about the woman and her likes and dislikes, she has probably clued you into what she prefers. And the whole dental hygeine thing is HUGE! Be clean there, please! Besides, its good for you as well! Go have fun!

Posts: 51

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1230Sharon wrote:
Did you see the guy in the "Black Tie" picture? His face looks so feminine. I thought he was a woman!
Totally! His suit was velvet and he's all model-pouty. The guy fashion photos are more vogueish and pretentious than the women ones. I would say just look clean, slightly more dressy than everyday clothing, and friendly. Also, NO untucked ill-fitting shirts, no sneakers (unless your date is something sporty), no sandals, and jeans with a nice shirt and a jacket looks very very nice on pretty much every type of guy I can think of. And cargo pants are not OK for a first date. Just giving my girly point of view. Girls often find it fun to put together a nice outfit, so as long as it looks like you put a little thought into yours, we will appreciate it.
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