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How to Dress for Success on Your First Date

So you've finally worked up the nerve and asked that cute girl you see almost every day in the coffee shop near work if she'll go out on a date with you. You might think that you can relax because the hardest part is over, but no matter how nerve wracking the asking was, I can assure you that the actual date is going to be just as (if not more) stressful.

There is one thing you can guarantee will go well though - and that is your first date outfit. There are also a few faux pas you can make sure to avoid, but as a barmaid who has watched many first dates succeed and fail I can tell you that if you nail the outfit, you can get away with (almost) everything else going wrong.

So go out, do some shopping, use coupons from sites like Discountrue.com if you want to save and have a few perfect date outfits ready and waiting for when you need them. If you're an average guy, I'm going to assume you're probably clueless about fashion in general, but especially about what works for a first date outfit - and what doesn't.  

Don't Go With the Scruffy Neanderthal Vibe 

Before you even open your wardrobe doors and start picking out what you're actually going to wear, PLEASE groom yourself. And by groom I mean clean under your nails, shave off that 5 o' clock shadow (or if you insist on having a beard then trim it, comb it and maybe oil it), get rid of the jungle taking root in your nose and ears, clean up the scruff at the back of your neck, and run a brush through that tangle you call hair.

DON'T wait until the day of your big date to get your hair cut because that freshly shorn look doesn't suit anyone, and please DON'T try a new hairstyle until after you've had at least 5 successful dates. Remember that first dates are like job interviews, only you're interviewing for the position of a potential life partner and you should want to look your best. 

Don't Wear a Striped Button Up and Tie 

I don't care HOW sexy you think that striped button up makes you look. Whether it's a pin stripe or a boat stripe, dress shirt or casual - whenever I see someone wearing one I think they've come from work. And unless they're at an event that calls for it, a guy wearing a tie is normally too uptight to be good boyfriend material. No matter what kind of date you're going on, something with a V-neck always works best.

It could be a polo shirt, a casual button up, a dress shirt or a tee-shirt. Leave the collar undone (but not so undone that we get a glimpse of nipple) and lose the tie the minute you don't need it anymore. A round neck is a bit too casual, unless you're wearing it underneath a button up. And if your shirt hangs below your belt then tuck it in, unless you're wearing it completely unbuttoned. 

Don't Even Think About Those Khakis  

Khakis, and especially chinos are probably the most versatile pants you own. They are normally super comfortable, and depending on the top you wear they can be smart or casual. But forget about them when you're planning your first date outfit. SERIOUSLY. There is just something about a guy in denim that sets our hearts a-pounding, and paired with the right accessories you can look as dressed down, or as dressed up as you like.

Overly distressed denim is out, but a slightly worn in look works well. Wear dark denims if you're going on a formal or night-time date, and light denims for a more casual, daytime date. And opt for denim that fits, not too tight and not too lose. We want to get a good look at your behind, but we don't want to be able to tell what kind of underwear you like. Also straight cuts are your best option, with narrow legs or even slight boot legs we might start wondering if you're shopping in the ladies department.  

Don't Forget a Jacket 

I don't care if you never suffer from the cold, or it is a hundred and millionty three degrees. Take a jacket. Girls don't have thick man skins and we often lose our jacket or opt not to bring one because it ruins our outfit. If you have one to slip over our shoulders when we get chilly your brownie points go through the roof. You also never know what the weather is going to do, and a shivering man with goosebumps is NOT attractive at all.

Sport coats exaggerate your more masculine features by making your waist appear narrower and your shoulders wider (a look we're drawn to whether we know it or not), and they can dress up even the most casual t-shirt and worn in jeans. You can't go wrong with a leather or denim jacket though, they give off a certain charming bad boy vibe we like a lot.

Don't Underestimate Your Shoes 

The girl you're going on a date with may not be a fashion diva, but if the planned activities for the date don't call for them and you show up in running shoes, dress shoes or (shudder) slip on loafers - you're tanked. You can almost never go wrong with leather shoes, and leather boots have the same effect on girls as leather jackets and well-fitting denim - we absolutely adore them.

Oliver Sweeney SS16
Oliver Sweeney SS16

At the end of the day, your shoes should suit what you're going to be doing on your date. Hiking boots for hiking, lace ups or Brogues for an evening date, sneakers (that haven't been worn to death), driving shoes or even moccasins for a daytime date and sandals for a day on the beach or by the pool (that's the only time they're acceptable). And please make sure they're clean and polished if necessary. Dirty shoes equals uncaring in our minds.  

Don't Go For the Gangster Or Punk Rocker Look 

When it comes to accessories for the first date, there is a fine line between just enough, too little and over the top. But walking that line is not too hard as long as you keep one thought in mind - would you show up to an interview with that on? Normally a nice watch is more than enough jewelry, although you can get away with a fine chain or bracelet that you always wear (not gangster style chains, or bracelets all the way up your arm).

PLEASE make sure your belt matches your shoes, because when they don't it can throw off your whole outfit and draw the wrong kind of attention to your crotch area. Make sure that it is not too heavy or chunky for the rest of your outfit, and that if the buckle is detailed it's not something too outrageous or kitschy. Again, it's going to bring the WRONG kind of attention to your crotch area and give the impression you're not serious about the date.  

Now that you have read this you should have a pretty good idea of what works well for a first date outfit, and these tips can apply to the all the "still getting to know you" dates that are hopefully going to follow. If you need to do some shopping to stock up on any first date items, then please don't do it on the day of the date - those clothing 'fold lines' and the new shoe smell are pretty distinct and will make you look like you're trying too hard.

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