Clothes shopping for the men in your life can be frustrating. If the guy in question is not accompanying you, you have to guess at their taste and their size. What's worse, not all stores size their clothes the same way, making the process all the more exasperating. Then there's the distraction factor: whenever I shop for a guy, I tend to start shopping for myself instead of staying focused, and wind up coming home with a pair of new sandals instead of the perfect button-up shirt. If he is there with you as you shop, sometimes getting him to accompany you and contemplate what you're picking out for him is a hassle, let alone shoving him into the fitting room with stuff to try on.
I haven't been doing this for a long time, but I like to think I have an impressive track record in this area. My brother once begged me to become his personal shopper after a jean jacket recommendation and a slew of sweet Boxing Day finds that fit him and his style. I've accompanied my ex jeans shopping post-breakup. My current boyfriend looks great in the graphic T-shirts I picked out for him. And more than one guy friend has suggested that he wants to go shopping with me at least once, just to see what I'd find.
If you have trouble shopping for the guys in your life, here are some tips that I've found really work for me:
If you're shopping alone...
Ask the guy for sizing info beforehand. This may seem like a no-brainer, but sometimes girls totally forget how easy this makes their lives. Find out shirt sizes (S, M, L, XL), waist measurements, inseams, and shoe sizes. Write these down if you have to.
Look at the store mannequins. If the guy you're shopping for is insightful enough to notice things like how he fits into a large at Mexx but is a medium at American Eagle, hallelujah! If not, a quick glance at the mannequins (are they tall and lean, or really wide in the chest and shoulders?) should help you determine whether you need to go one size up or down.
Compare clothing sizes. This might earn you dirty looks from the employee hovering over your shoulder ready to fold the six sweaters you just messed up. But sometimes it helps to lay one piece of clothing over another, just to see what the difference is in sleeve length, torso length, etc.
Use colour cues. Does he have blue-green eyes that the right shade of teal will accentuate? Or maybe his skin is a warm, dark tone that will look great with saturated maroons and oranges? Is there a particular hue that he wears constantly that you feel really complements him? Keep these things in mind as you browse the racks.
Know the store's exchange policy and get a gift receipt--just in case. Sometimes, despite your best intentions, the gift you picked out might not fit or might not be to his taste. In that case, ask for the details of the store's policy, and include a gift receipt with your purchase so that he can exchange it himself if he needs to.
If you're shopping together...
Don't get distracted! Head to the men's section and do a thorough perusal before even thinking of looking through the women's department. This will help keep you focused on looking for stuff for him. If you really want to go through the stuff you skipped, hey, it's a good excuse for a second trip by yourself or with girlfriends.
Open your ears to his input. After all, he's going to be the one wearing the stuff. If he sees a sweater he likes, find one in his size and encourage him to try it on.
Make him try things on. For some strange reason, most guys seem to think that they don't need to try anything on, and something which proclaims itself to be the correct size will fit him perfectly, as if by magic, and he will look as handsome as Brad Pitt with it on and live happily ever after. As his co-shopper, it's your job to give him a reality check. If he doesn't believe you about this shopping step being necessary, snag a store employee, preferably a cute one, and get her (or him) to extol the virtues of trying clothes on.
Be honest... If the pockets on a pair of jeans aren't working for him, say so, but blame it on the pants' design instead of his large/flat/non-existent butt.
...but lay it on thick with the compliments. When something looks good on him, gush! If he tries on something that's a little too adventurous for his taste but looks great, gush! The lavish compliments become the tipping point in the decision-making process. Have you ever seen Clinton and Stacey do this on What Not to Wear? It does wonders for self-esteem and helps him come around to your point of view.