lace-up ankle booties: See by Chloe, bought at The Bay
pants: American Apparel
red jacket: Ralph Lauren

“Clothes make the man. Naked people have little or no influence on society.” – Mark Twain

I would like to start this post off by saying that I in no way claim to be a fashion expert of any kind. One thing that I do know, however, are cute boys, and well dressed ones at that. So with that on the table, I give you some of the biggest dating outfit faux pas’ I have seen, along with an alternative of what they should have worn.

Puma Drift Cat II Shoes

First Date Faux Pas #1: Running Shoes

If there is one thing I hate almost as much as Crocs, it’s when a boy wears the shoes to the left, or any other kind of running shoe, with pants. An exception can be made after the first few dates for a pair of classic Adidas, but generally speaking, running shoes with pants are the UGGs of menswear. Athletic footwear needs to be worn only when it is appropriate, so if you are wearing runners, you better be actually running. Too many times I will see a cute boy walking down the street, and then I look down and he is wearing runners with his too long jeans. I’m almost thankful that they do, as I would hate to have to see the rest of their wardrobe. It’s a huge turnoff. Huge.

Mark McNairy - Chukka Boot Navy

First Date Faux Pas Fix #1: Red Soled Shoes

Contrary to the turn off of the running shoe, the red brick sole on these Navy Suede Chukka Boots are as much of a turn on as the baby blue eyes of a cute boy. These shoes are universal in that they aren’t too dressy, nor are they too casual (especially compared to the alternative above), and can be worn well with most pants. Just make sure you don’t wear them with trackpants!

Alternatively to the Chukka Boot, you could go for A.P.C’s Derby Brick Sole, or these beautiful Mark McNairy (who is now my favourite mens shoe designer it seems) Red Brick Sole Penny Loafers. Please, let the next person I date have a pair of red brick soled shoes.

Abercrombie Gothics Mountain Hoodie

First Date Faux Pas #2: The Hoodie

I’m starting to sense a trend here, are you? Sportswear should not be worn on a date, unless the date is playing sports somewhere (which, actually, if the girl is athletic, isn’t such a bad first date), or you are under the age of 25. If you are over 25, you should not be shopping at this store unless it’s for pajamas or cottage gear (even then.. I’m hesitant to encourage it). Don’t get me wrong, I used to love Abercrombie, and the boys who wore it (ermm.. the models); but that was when I was 19. I’ve grown up now, and I want a man, not a boy. Regardless of the brand (it could be American Apparel even), a hoodie should never be worn on a dinner, coffee, or drink first date.

Martin Margiela 10 Stitched V Neck

First Date Faux Pas Fix #2: The V Neck

V Neck’s are not just for girls who want to show some cleavage, you know. The V Neck sweater is hands down the best alternative to the hoodie. It always looks classy and put together, and it lies on the fine line between casual and dressy, so you can wear it to any date type without the fear of being over, or under, dressed. Bonus points if you wear a colourful shirt underneath (orange or coral is personally my favourite) to show a little imagination. You could also go for a brighter V Neck, like this one (I have such a crush on this model now). A nice alternative to the V Neck is a button up cardigan, another sweater with which you can never go wrong.

Burton Arctic Jacket

First Date Faux Pas #3: The Snowboarding Jacket

Yes, we get snow in Toronto. It also gets really cold in Toronto. You should not be wearing a jacket that you wear while carving it up on the hill, to a date. But, it’s really cold, and you have to get to the date in the cold, right? That, folks, is why cab drivers make more money in the winter time than they do in the summer. I love a boy on a bike more than most girls, but when winter hits, it’s time to pay for the convenience and take a cab to a date. Or, you can walk, but you will be a bit colder.
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B:SCOTT Denim Double Mock Pullover

First Date Faux Pas Fix #3: The Classy Pullover

You can either go for the standard peacoat (which gets a little boring), or you can have a bit of a dressy casual look with this pull over. A little bonus for the girl if you take it off and your other shirt gets caught, and she gets a peek at your abs. Mmm. I like this one a lot.

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Birkenstocks, with socks

First Date Faux Pas #4: Sandals

Yes, the image is of someone wearing socks with Birkenstocks (which is a notorious faux pas by now), but what it says above should not be lost on you: I’m talking ALL sandals. Sandals should not be worn on a first date, unless you frequent salons and get a monthly pedicure like us girls. Girls can get away with sandals because we have pretty feet, and have pretty colours on our toenails. Boys, your feet are gross, and we don’t want to see them. NO Sandals. No no no.

TOMS shoes

First Date Faux Pas Fix #4: Shoes sans chausettes

It’s hot out, it’s summer, I get that you don’t want to wear socks. Well I don’t want you to either! Shoes without socks can look so classy and stylish, as long as it’s the right type of shoes. If you must embrace your hippie birkenstock ways (I, by the way, ROCK the birkenstock look, but only after a pedicure), then go for a pair of TOMS shoes. For every pair you buy, they give a child in need a pair, so it’s for a good cause. Also, the canvas and linen material are comfortable, and breathe nicely for those hot steamy (err.. sweaty) days.

Alternatively to TOMS, you can go for the extremely trendy boat shoe. Everyone, EVERYONE, has these right now, so they are easy to find. They look great without socks, with a slight roll on your jeans.

Baggy Jeans by Triple 5 Soul (does this brand even exist still? I guess so!)

First Date Faux Pas #5: Baggy Jeans

Last, but certainly not least, our dear old friend: The Baggy Jeans. Baggy jeans NEVER look good (unless it’s a cute girl rocking them), and a tailor is your best friend. Even the movie Clueless touched on this and that was from 1995. Baggy jeans make you look sloppy, makes you look out of shape, and worst of all, they cover the nice shoes that we learned about above.

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Kicking Mule Workshop 1980 Hand Dye

First Date Faux Pas Fix #5: Fitted Jeans

Boys, if you wear slimmer fitting jeans, it does not make you a hipster, or gay; it just makes you style aware. In fact, super tight skinny jeans on men is a bit of a turn off in itself. The jeans to the left are gorgeous, but they are definitely a little pricey. Some really good alternative denim labels are A.P.C, Nudies and good old traditional, Levi’s. Bonus points if you roll them up in the summer time (instead of shorts; I really hate shorts on boys), with the shoes above.