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I basically grew up on the runway. My mother was a model when I was younger, so I was introduced to that world early in my life. My first job was at 9 as a ring bearer in a bridal fashion show. Then I was in prom fashion shows and worked my way up to groom in bridal shows.
Eventually, I worked as a fashion editor for a glossy magazine in New York City. What I’m getting at is that I grew up around fashion, love fashion, and know how important it is in the dating world. I know there are a million “what to wear on a date” articles out there, but I wanted to throw in my two cents.
I can’t believe I have to address this basic concept, but make sure you’re freshly showered. Also, make sure your fingernails are clean and clipped (yes, she will check). You want to present your best self.
I know there’s the whole “I want her to see the real me” mindset, but that is for later. If she showed up in sweatpants and dirty hair, you’d probably have quite the negative reaction. Show that you care and are putting the bare modicum of effort into the date.
I would recommend getting a haircut right beforehand as well. When we make a change to our appearance, it makes us feel confident and good inside. If you’re over 25, please leave the $15 haircut behind. Find a decent, mid-level barber or salon and pay at least $25 to $30 for a cut. There’s a big difference. You may not notice it, but I guarantee you that she will. For very important events, a $50 cut will make you look amazing.
Facial hair is a style choice, so it’s OK to have some if it’s well-trimmed. I like to be clean shaven sometimes and scruffy other times, so it’s up to you. But if you have a spotty beard or it’s different lengths, go for the smooth look. These are bad examples, and these are good examples
There are lots of different styles guys look good in, so basically you want to accentuate your own personality or nature. Style is definitely not one size fits all. Someone dressing for a date in Portland, Kansas, and NYC are probably going to have vastly different looks.
The exterior world mirrors the interior world, so you want to bring what is inside of you outside. In the simplest terms, if you’re an outdoorsy type, don’t try to go with the skinny-jean look. If you live in a nice suburban area, maybe the rough-and-tumble look isn’t for you.
Identifying and dressing for your style is a lifelong skill, so don’t worry if you’re not sure what it is or how to dress for it. You can start with something standard and build from there. A nice pair of jeans and a blue button-up or golf shirt will usually work for every situation.
Let’s get into the nitty gritty of the actual clothes you wear on a date. Again, I shouldn’t have to say this, but make sure the clothes you’re wearing are clean, stain-free, and in good shape. Yes, having some ripped jeans or worn-in jackets can be very cool, but make sure they’re meant to be that way and aren’t ragged from overwear.
All pants must have a belt. Not only does it help keep your pants up, but it’s part of a complete outfit. The color of the belt and the color of your shoes must be the same or complement each other. No brown belt and black shoes.
Since we’re on the color talk now, socks should be the same color as your shoes. They can be colorful and fun but never white athletic socks. White socks with dark shoes is the number one thing NOT to do. Like, ever.
And now that we’re talking about shoes, make sure they’re clean and unscuffed. I personally don’t like to wear sneakers on dates, but if you do, make sure they’re top notch, not stained, and go with your outfit. I think a pair of black slip-on shoes will go with almost any outfit. If you get another pair in brown, you’re pretty much good for any outfit.
Get a shirt that fits you. Ask the woman in the store to recommend one for you if you’re not sure. Having a shirt (and clothes, in general) that fit you properly is a huge thing.
If it’s jacket weather, get a decent medium-weight brown or black jacket. No fleece, no Carhartt, no big, puffy winter jackets. You can always dress in layers underneath it.
I have to say that I wish men could dress and use more accessories as women do. Women have earrings, hats, rings, necklaces, hairpieces, bracelets, bags, and baubles. Yes, men can wear all of those things, but we have to make sure it’s tasteful and doesn’t make you look like an aging Johnny Depp wannabe.
That being said, accessories are what can catapult you from a standard outfit to a super hip or classy one. If you aren’t sure how to go about it, start with a nice watch. Other accessories to consider are funky belts, colorful socks, a pocket square if you wear a sports jacket, fun cufflinks on French cut shirts, and cool ties.
I also have some simple necklaces and rings that I don’t wear much, but they’re fun for the right time. Earrings are fine as well if that’s your look. A nice wallet or money clip can also go a long way.
Again, though, you want to make sure that your accessories match your style. You don’t want to wear a suit and a cowboy hat or go “lumbersexual” and have a bright gold watch. Feel free to experiment a little and see how it goes.
I think one of the best things to have on is something that invites conversation. Many times on dates we’re a little anxious or unsure of what to talk about. Having a go-to physical thing on us gives us something to talk about and stories to tell.
For instance, every time I go somewhere on vacation or travel, I like to grab a small thing. Maybe it’s a tie, ring, or shirt. That way, if someone comments on it, it gives you something to talk about and helps tell the story of who you are.
It can be something you got on your travels or something fun that draws people in. Sometimes on a casual date, like going to the beach or volunteering, I’d wear a fun T-shirt. It invites curiosity and makes people laugh, and you can watch people surreptitiously checking you out to figure out what it is.
I also loved finding interesting clothes at the Salvation Army, Goodwill, or the local thrift store when I was younger. I loved trying to breathe new life into old and funky clothes. My friends and I even had an Ugly Shirt Night where we all bought the worst shirt we could find and wore them out. We had people lining up to talk to us all night!
As with many skills and endeavors, when it comes to style, start with the basics that you’re comfortable with. Then slowly start to expand your tastes. Try out new things, and be open to some criticism and advice.
But remember that you always want to feel comfortable in what you’re wearing. If you’re ill at ease or trying to pass off a look that isn’t authentic to you, it’ll come across in your body language. If you’re still in doubt, find a picture of a male you admire and see if you can try and emulate his look.