A great general guideline for getting ready for a date is that it’s really all about appropriateness. Figure out the situation you are going to be in, such as where you’re going on the first date. You’re not going to wear the same thing to a picnic on the beach as you would for a night at the theater.
So when you call a day or two before, let your date or girl-friend—if it’s a woman—know what the plan will be for the evening. For guys, when you’re taking that extra time and putting some thought into the relationship, your date will really appreciate your efforts.
Going on a date is kind of like going on an interview (well, not exactly)—you want to make the best possible first impression. A good rule of thumb is to overdress just a little bit and always wear a sports jacket.
A sports jacket or a blazer will really dress up any outfit, and once you get inside, like at a restaurant, you can take the blazer off. A fabulous all-purpose outfit is a casual pair of slacks (not jeans), a relaxed sports coat, a solid watch, and a great pair ofloafers. Just no pleats, please, for your slacks, because they make almost everyone look dumpy and fat.
The details, baby
It’s really all about details, details, details. A sharp watch—it doesn’t have to be expensive, just something steel, or even a Swatch—a nice belt, and a great pair of shoes will make any outfit shine.
In the ’90s, we got into a baggy trend, so most guys are not educated as to where an armhole should actually fall. Details of fit are actually very important. The shoulder of the sleeve should end at your shoulder or fall just a little bit over your shoulder. Your shirt or sweater should look like it’s made for your body.
A fitted dress shirt is always an excellent choice. Buy from a department store where you can develop a relationship with a salesperson who will lead you in the right direction. If you have a long-term relationship with a salesperson, he or she will have an investment in finding fabulous outfits for you. And then you will have a fairy god-stylist—like me—all to yourself!
Below the belt
Details also matter in the areas that your date may or may not see. Boxers are hot! And by “boxers” I mean the guys with gloves. But I’m really going to go with boxer-briefs because they’re comfortable, plus you get all the great bun-hugging qualities. If the date goes really well, it could be a bit weird or totally kill the moment if you’re wearing tighty-whities. No offense, boys.
Like I say in my book Off the Cuff, a lot of men think that to look slim, you have to wear all black. But by doing so you
can end up looking dreary and pale. I say, stick with monochromatic solids for the top and the pants. A nice alternative to black is a chocolate brown, which is flattering on everyone, so pair a chocolate brown sweater with brown pants, or a navy turtleneck with navy pants. Just keep the top and the bottom the same color.
Also, it’s great to be in shape, but if you spend a lot of time at the gym, and you’re super pumped-up, remember: You shouldn’t have larger breasts than your date’s.
What not to wear
I don’t like to have too many no’s in my vocabulary, but banana hammocks are always a fashion don’t. Also, say nay to really tight European thong swimsuits. And also never wearsandals with socks. You have to ask yourself, “What would Jesus do?” He would not wear the two together. And say no to gauchos and clogs. These are bad!
In terms of texture, the first rule is, never wear anything sheer. My motto is if it feels good, wear it. You can never have
too much cashmere.
Any crazy jacquard is probably too much. All traditional menswear should be fine—but jazz it up with color. Work with accessories and color.
Feel good, look good
How you look on the outside tells the world how you feel on the inside. You carry your clothing with you everywhere, and it tells people what you’re about and who you are. It’s your uniform.
When you wear a great outfit, you feel confident, and confidence breeds success. And there’s nothing women find sexier than confidence.
About the author : About the Expert: Carson Kressley serves as the fashion expert on the popular television makeover show Queer Eye for the Straight Guy. In his professional life, Carson is an independent stylist who spent many years working with Polo Ralph Lauren in New York City, specializing in the design aspect of the men’s sportswear division. He also supervised fashion styling for the company’s national retail advertising campaigns. He is the author of Off the Cuff: The Essential Style Guide for Men—and the Women Who Love Them.
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