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9 Essential Clothing Pieces Every Man Needs To Win at Dating

If you've ever gotten ready for a date in your life, you know the most nerve-wracking, and often time-consuming, part of it is trying to figure out what to wear. This is both true for guys and girls, but guys sometimes are even further gone when it comes to dressing themselves for a date. We've all been on dates where the guy is either dressed like a total slob, a total prick, or a total douchebag. For those who are the latter, it seems like they tried -- just not enough, but that can be better than trying too hard.

If you're looking for help on what to wear to your next date with your latest match, look no further! Here are some tips and examples of what a great, casual first date outfit looks like, so you'll never be overdressed or underdressed again.

  1. Long-Sleeve Polos

    Long-Sleeve Polos
    Image Credit:

    Depop User: sawyersteeze

    If you wear it right, and find the ones that don't look like dad-shirts, polos can be your best friend. They look great on guys because long-sleeve styles are different than the norm, and they seem to fit slimmer, usually, along with a neat collar. It's a perfect option for when you want to want that formal feel of a collared-shirt but don't want to arrive overdressed.

  2. Sneakers

    Sneakers
    Image Credit:

    @jaybeezishangintough

    For most people, the first thing they look at in terms of what you're wearing is your shoes.

    If you want to make a good first impression, you should pay very close attention to what you have on your feet. When it comes to casual dates, there's nothing better to wear than a good sneaker that proves you can have both comfort and style. Shoes like Vans are a no-brainer, but if you want to opt for something a little more upscale yet not too flashy, try out a pair of funky shoes, like these Nike Air Max 97's pictured above.

  3. Cool T-Shirt

    Cool T-Shirt
    Image Credit:

    @tonimahfud

    Simple, yet powerful, a good t-shirt can go a long way when it comes to style and wooing your date. Don't make the mistake of wearing those awful graphic tees you see in a stack at your local JcPenny's, though, with random cartoon and superhero characters. That's about the worst thing you could wear on a date.

    Instead, go for something more street style, and wear a shirt with a simple phrase or logo on it.

  4. Distressed Denim

    Distressed Denim
    Image Credit:

    @menwithstreetstyle

    Whether worn as a jacket or on your legs, distressed denim is a good look for anybody. It's become one of the most popular fashion trends in the last few years, and it's clearly here to stay. Distressing on your denim adds a bit of flair to the regular jeans you can wear any other day of the week. If you're trying to look a bit more put together, ironically, you can wear ripped up jeans with holes in them! It gives you that bit of an edge.

  5. Statement Jacket/Hoodie

    Statement Jacket/Hoodie
    Image Credit:

    @vincenzoragnacci

    Layering pieces are always good, and they have the opportunity to make your outfit complete or add a little something to an otherwise basic outfit. If you have a really cool jacket you've been dying to wear, a date is a perfect excuse to wear it! Make your jacket or hoodie the center of attention of your outfit by layering it over essential and fitted pieces of clothing.

  6. Flannels

    Flannels
    Image Credit:

    @simple.fits

    A staple item in anyone's closet, you can never go wrong with a flannel.

    If you're going on a date that doesn't require a three-piece suit, then a flannel is your best bet. You're able to dress it up or dress it down, depending on what you're feeling, which makes it versatile yet stylish. Also, it'll keep you warm for those outdoor date ideas, and you can give it to your date, too, if they're feeling cold, showing what a gentleman you are.

  7. Accessories

    Accessories
    Image Credit:

    @ill_fortune

    Who says only women are allowed to accessorize?

    Nothing is more unexpectedly sexy than when a guy knows how to accessorize himself and pulls it off. If you're not quite yet an expert, though, that's okay. One accessory you can never go wrong with are watches.

    Watches add a touch of elegance, if they're the right kind, and have a way of making it seem like you have your priorities in order. The best part is, you don't need a Rolex to look sophisticated -- instead, you can go for this Gold Classic Collection Casio watch, that looks just as good with a sleek design.

    Speaking of gold watches, gold jewelry is even better. A simple chain can really make all the difference in spicing up your outfit. Gold rings also look so good on a man, and your date will definitely notice.

  8. Socks

    Socks
    Image Credit:

    @christosnewyork

    Believe it or not, girls look at socks.

    You may have noticed a recent style trend borrowed from skate culture that's been going around of cuffing your pants and exposing your crew-length socks. They usually have cool designs or patterns on them, and it's actually quite a good look. Your choice of socks can definitely act as an accessory to the outfit. Simple white crew socks usually do the trick, like these here pictured, but you can also get some socks that have fun colors or prints on them and pair them with a basic-colored outfit.

  9. Casual Dress Shirt

    Casual Dress Shirt
    Image Credit:

    @menwithstreetstyle

    Sometimes, a nice ironed dress shirt is needed for the occasion. If you do want to wear something that's both casual yet classy, then this is a perfect fit. You can dress down your shirt so that it's not too much by pairing it with your favorite pair of jeans, as shown here.

  10. If you're looking for more inspiration or resources to check out outfit posts, head on over to Instagram. Users like MenWithStreetStyle, and searching up hashtags such as #outfitgrid, #style, #ootd, #menswear or #mensfashion, can lead you to thousands of ideas and pages dedicated to men's style, and will have you looking like a million bucks for your next date.