8 Clothes to Not Wear on a First Date …

Planning your wardrobe for a first date is frustrating, even a little scary. You want to make a good impression, and in your desire to do so, it’s not uncommon to choose clothing that you really shouldn’t be wearing. I know that, back when I was still going on first dates, I’d make bad decisions, like going with something too formal or something I thought was flattering, that really wasn’t. If you’ve suffered through fashion foibles like this as well, check out all the clothes to not wear on a first date.

1. Shirts with Messages

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Of all the clothes to not wear on a first date, shirts – especially tee shirts – with messages on them are probably the first verboten choice. Whether it’s a funny message or a political message, you want to avoid advertising either your beliefs or your sense of humor on your clothing. Later, with someone you’re seeing regularly, this is acceptable. On a first date, however, when you don’t know the other person’s humor or political leanings, you can make a bad impression at best, and even start an argument at worst.

2. Revealing Attire

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Revealing clothing is also a bad idea on a first date. You don’t have to dress like a stodgy Victorian or like a Puritan, but you’re going to want to avoid anything too low cut. Likewise, steer clear of fishnets, extreme mini skirts, and things like that. You want to make a good impression, and if your outfit’s too revealing, it’s going to send out the wrong messages.

3. Daring New Trends

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I don’t mean that you can’t be trendy on a first date, not by any means. However, this definitely isn’t the time to try out some extreme new trend, especially if you’ve never before worn it (although I’ll expand on that point in a minute). The rule of thumb concerning clothes to not wear on a first date is that you need to be sure it looks good first.

4. Lingerie

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Obviously, you can wear lingerie under your clothes – that’s what it’s made for, after all! However, wearing visible garters, bustiers, and things like that, as your outfit, well … those aren’t the greatest pieces. The first time you go out with someone, remember, you do want to make the best impression. This kind of clothing, again, can send out the wrong signal.

5. Risque Shoes

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There are also certain kinds of shoes you just shouldn’t wear your first time out with someone new, beginning with really risque heels. You don’t want to wear six inch stilettos or clear heels. For one thing, you’re going to be incredibly uncomfortable, especially if you have to do any walking. For another thing, these are yet more items that can give a guy the wrong idea.

6. Sandals with Socks

I cop to occasionally wearing sandals with socks when I’m just hanging out or something, or if my jeans will cover up my sins. On a first date, however, avoid this look at all costs. It can be a comfortable combination, but so often, what feels comfortable actually comes off as dorky … and this is one of those instances.

7. Anything You Haven’t Tried On

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Concerning clothes to not wear on a first date, you definitely don’t want to wear anything you’ve never worn before. That doesn’t mean you can’t go out and buy a new outfit. However, make sure you’ve not only tried it on, but wear it around your house beforehand. Vacuum the house in your new threads, or something, and model the outfit in front of your friends. Make sure it looks all right, and that you’re comfortable. In fact, that brings us to–

8. Ill-Fitting Clothing

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Those skinny jeans, that tight fitted shirt, or that new, tight skirt might look really good on the hanger, but that doesn’t mean they’ll look good on you. If there’s any chance of buttons popping, zippers falling open, or fabric ripping, keep that article of clothing in the closet. Whether it’s too big or too tight, it’s not for tonight.
There aren’t really a lot of clothes not to wear on a first date, it’s more about using good judgment and common sense. There are certain articles of clothing that simply shouldn’t be worn when you’re first getting to know someone – or at all. What’s your idea of an ideal first date outfit?


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