Dress Him Like Beckham

I'm fussy, very fussy when it comes to clothes and ten bucks says your boy is too.  Whether he's fussy because he's a discerning buyer, or fussy because he simply doesn't want to wear something new is a moot point.  The bottom line is that guys won't wear anything they aren't comfortable in.

The first thing you need to do is realize that the clothes you like, and the clothes he likes, are always going to be different.  There's no silver bullet here where after reading this article you'll have an insight so deep into the male psyche, that the next time you take your man shopping he'll twirl out of the change room looking like David Beckham.  That simply, just isn't going to happen.

What you can do though, is accept that change will take a bit of time and you need to have a strategy and be patient. You may have a boy that is comfortable trying new things, but for most guys departing from their tried and trusted get up is a seriously awkward and uncomfortable experience.  It takes most of us lads so long to get comfortable with something (and most of the time shopping isn't that pleasant) that he's probably going to go with what he knows, but in a different colour…

You need to start by getting your man a good base of simple, well cut clothes that he can style up with something new.  Check out my 10 favourite things article to get a good base going on - If you can't be bothered with more homework reading that then make sure he has these three essentials:

1. A good pair of well cut jeans.  Diesel if you wallet can stretch, otherwise Lee are a good bet.
2. Some stylish trainers - white or black Converse All Stars are my picks.
3. A plain, t-shirt that isn't too busy with logos or pictures.

Once he has these things and assuming you're looking to dress him up away from work, then make SURE he is wearing these when he goes out shopping with you.  If you want to get him a fun shirt for the pub and he goes out in his trakkies, then he may not be appreciate the genius of your intended look.

Keep the shopping for the new item short and sweet - go specifically to get him an item and once you have it then bail.  Trust me, he'll love you not making him shop all day and he may even associate shopping for new items with a pleasant experience.

Also, if you have time to check out the shops before hand (no need to answer me on this one) then you won't spend all day trawling through shops exhausting his patience and if you're really on the money wait for the sales.  Most guys love to save a buck and if he can get a new item and save some cash off the retail price he'll be stoked.

Now some things are going to take time to talk him around to.  In my case it's smart shoes - in fact I can hardly push myself into a pair and give me half a chance and I'm straight back into my worn out Vans!  But my girl Jess was patient and had me looking at enough shoe shops and suggesting enough different pairs that when I saw a pair I liked I was sweet with buying them.  She's awesome like that, I think it is part of some sort of repetition strategy on her part - repeat how much I need a new pair of shoes and suggest enough different pairs and eventually I give in, buy a pair and I'm comfortable wearing them.  

So, to avoid building up a collection of clothes at the back of his wardrobe:
1. Get him a good base of clothes
2. Make sure he is wearing clothes shopping that he'll wear with the item you're looking for.
3. Do your research before hand to find candidate items
4. Wait for the sales (if you can)
5. Repeat until well styled.