Question: 

At what point in a relationship is it appropriate for your significant other to criticize what you wear?

On a recent trip to the Caribbean, that was supposed to be a romantic getaway, I decided to change into a pink off-the-shoulder tunic that I absolutely adore.  It has a string of multi-colored pink pom-poms tiered on a braided cord.  I intended to wear it as a beach coverup.  My boyfriend clearly didn’t take to the look.  He kept asking, “What is that hanging there?” And something like, “Why would you wear that?”  Granted, we kid around with each other – I call him Bighead, but that’s more like a double-entendre. (Hehe)  Anyway, he proceeded to inform me that it’s something he would give his 10-year-old. I felt he was getting pretty liberal with his commentary needed to be reined in.  You see, this was our very first trip together after three months of talking on the phone; we’ve known each other most of our lives, but only as casual friends.  We were still sorting out this new version of our relationship.  We’ve decided that we’re in love.  That said, I’m a practical girl.  I’m not lead by emotion and having been single most of my life, I have a pretty good idea of what I stand for and the sacrifices I’m willing to make to compromise and make my relationship work.  But I’m also an independent woman who needs to be respected.  So my response was to establish a “New Rule: If you didn’t pay for it, you don’t get to criticize it!”  I said it as nicely as possible.  I believe I put a smile on my face to force myself to not have an attitude about it, but not a big enough smile to make him think I wasn’t serious.

It took me a month to pack my suitcase! I thought I was satisfied the first time I packed, but as time went on and I thought more about what I would need and how I wanted to look, I decided to reconsider everything.  I put back half the things I had packed when I realized I had enough for a week, not three days!  Then, like I said, I had to reconsider what I wanted to look like. What experience did I want to help create for us through what I wear.  See, what a woman choosesto wear is not only self-expression but atmosphere transforming. What impression do I want to make? Where that pink tunic fell into that context is ‘ beachy, fun, silly, youthful.’  The flip side of this situation is what it tells me about him at this early stage of our relationship.

The Top Three Things I Learned About My Boyfriend Via My Wardrobe

One impression of him i solidifies is that his personality is more on the serious side.  I’ve said this to him.  He does have a sense of humor and we laugh a lot (mainly because of my lightheartedness, to be honest) but his disposition is serious.  He is divorced and perhaps this is due to the experience that lead to that conclusion, as well as his sense of obligation to his children and the family business.  Whatever the case, the bottom line is that he is more of a serious, conservative person.

The second impression it gives me is that he does have an expectation for how I am to look for him.  This surprised me a little because he has made statements about being a more casual dresser – jeans and a nice t-shirt – although not against dressing up a bit when it’s called for.  When I talked to him about my challenges with packing well for the trip, he told me I don’t need to give it that much effort just for three days.  But in the back of my mind I know my man would want me to look good for him, therefore I took his input with a grain of salt.  If nothing else, I have to look good for me. Looking back, I am adding up the comments he made that make it clear he ispaying attention and what I wear doesmatter to him.

The third thing I have learned about my new boyfriend is that he will definitely complement me when he is impressed with how I look, and it doesn’t require overt sex appeal.  It was the outfit that covered me nearly head-to-toe that got a rave review: “You look really beautiful in that outfit.”  It was a pair of grey lounge-y, refined sweater pants with a grey hip-length tunic with embroidered cut-out floral design, and sparkly dark grey platform open-toed sandals.  When I walked toward him at the outdoor bar where he was waiting for me, his associates turned around to watch.  I think that did it.  I’ve also figured out that he prefers neutral tones like grey, tan, navy blue, brown, black, etc.

The moral of the story is, I am willing to dress the way my man likes, but the decision is mine to make unless he foots the bill for my wardrobe. (Gotta work on that!)  In the meantime what I amwilling to do is avoid wearing things I know he definitely won’t like – but ONLY if it’s convenient for me!