We all know most men are not big on shopping, unless it's an actual hobby for them or they're just naturally fashionable. Shopping doesn't come easy to most men, and we bet your boyfriend's one of them. Find out how make his shopping experience equivalent to attending a Lakers game. Well, maybe not that exciting, but you can try!
When you're shopping with your man, let him know that you love his effortlessly casual style and that the shirt he's wearing really brings out his eyes. Or compliment his clothing and relate it to one of his body parts in a positive way. Butter him up with a couple of these type of compliments to put him at ease and chase away the anxiety when you mention the "F" word (we mean "fashion," of course).
After you've softened him up with compliments and heightened his confidence, subtly start picking out clothing for him that you think he would like. Start slow or else he'll start to notice your tactic. Casually pick out a collared shirt or casual tee and tell him how great it would look on him and why. Telling him exactly why is important because then you have a particular reason for picking that out. For example, tell him the collared shirt would look great on him because it has the clean-cut look (or whatever look he likes) that he tends to go for.
Unless you're dating Chuck Bass, your boyfriend will be into sales. The casual guy will love sales because he'd rather spend his money on "more important" things (although what's more important than clothes? I, personally, don't get it). At any rate, direct him toward the sale rack. If he's iffy about sales because he thinks they might be last season's styles, assure him that's not true -- and even f it might be, no one will (hopefully) notice.
By this time he should be more comfortable with shopping and maybe even enthralled by looking for clothes for himself -- so you could sneak off and get your shopping in. You can mention that you're leaving to shop for yourself now or you can just disappear -- it all depends how high his anxiety level is.
If you really want to make this shopping experience a great one for him, try on some lingerie and let him take a peek at you in it. He won't mind shopping with you after that!
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