Top 10 Things Guys Should Not Wear on a Date

1. Tennis Shoes (or Crocs)

Unless you’re an American tourist, tennis shoes should only be worn when you’re actually playing tennis. Not with jeans, not with a dress shirt and most definitely not on a first date.

Go for a pair of equally comfortable but stylish sneakers instead – Onitsuka Tiger Mexico 66 sneakers are a personal favourite.


2. Oversized Polo Shirt

Oversized polo shirts are what Mom Jeans are to women – outdated, unflattering and something only your parents would wear.

And whatever you do, never tuck your polo shirt into your jeans.

(Source: Dr Jays)


3. Man Jewellery

A watch is OK. A leather cuff is acceptable, but only if you’re a rock star (or generally more stylish than the average Singaporean male). Anything more, however, will make you look like John Galliano (and trust me, that’s not a good look at all).

Are you a peacock? No? Good. Now listen to me and leave the shiny baubles for the ladies.

Mickey RourkeMickey Rourke may have a tough guy reputation but all of this – and I mean all –  is negated by his man necklace. (Source: Fanshare)


4. Anything shiny

Don’t get me wrong – I’m attracted to shiny things like a magpie.

However, unless you’re a Kpop star, avoid wearing anything shiny or sparkly. This refers to jackets, shirts and above all, pants.  Just trust me on this OK? Not many men can pull off shiny pants without looking completely ridiculous.  And if you’re reading this for fashion advice, then you most definitely can’t.

(Source: Geometric Sleep)


5. A Crumpler bag

Okay, I’ll admit – Crumplers were in when I was still in school. All the cool kids had one and it was sort of like the Chanel 2.55 of school bags (okay okay, Coco Chanel is probably turning over in her grave right now, but you get what I mean). That was also six years ago.

The bottom line is – if you’re not a teenager, you shouldn’t even think about bringing a Crumpler bag on a first date (or to work).

Besides, what could you possibly need to put in there that can’t fit inside your pockets?


6. Anything with Velcro

I don’t know how else to put this but just….don’t. Velcro wallets, shoes, shirts (oh my lord) and the like should be stored away in a place where the light don’t shine. Repeat after me: Velcro will not make me a chick magnet.

(Source: F5toRefresh)


7. Slippers

Most men have ugly toes. Don’t take offense at this – after all, it’s not like you can waltz into a beauty salon and get a pedi while watching last season’s episodes of Gossip Girl can you?

Whatever it is, wearing slippers on a date is not a good idea. Your date will be too distracted by your gnarly toes to listen to the conversation.


8. Man Shorts

…especially the kind that end at mid-calf. Unless your date is at the beach, ditch the bermudas for a pair of slim-cut jeans. Nobody wants to see your hairy legs okay? And heaven knows that man shorts do nothing at all for your butt.

(Source: Chambers Street)


9. Guyliner

Do I really need to go into detail about this? And no, Adam Lambert is not an excuse for this.


10. Clothes with logos

Unless you’re Cristiano Ronaldo himself, wearing a brightly coloured jersey with his name emblazoned on the back is just plain tacky, and should not be worn on a date. As is wearing a bright red jacket with Ferrari logos printed all over.

(Source: Soccer on Sale)

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