There are layers of reasons a woman asks how she looks in clothing. As annoying as it may feel to you to constantly be asked this question, you need to answer and be sensitive every time. Every. Time. I know sometimes it feels like there is no good response to this question but no answer feels like you agree (that she looks fat) and don't want to admit it. And let me tell you that hurts. Being frustrated with your wife because she takes too long to get ready because she gained weight and no longer fits in her clothes hurts. Especially when the weight in question was gained when growing a baby. All of the problems are escalated when it is related to pregnancy or new motherhood.
When you're being asked that we are looking for honesty...but nice honesty. Sometimes we're asking to confirm that something is unflattering. We know it looks bad so when you say "Oh, you look great!" we know it's a lie. Which means you don't care if we look awful when we go out in public. That's not helpful. You may feel like you covered your butt but it's frustrating to think that your husband is willing to let you walk around looking like you've been shoved in sausage casing to save some face. Thanks. I'll appreciate that a ton when I bump into that genetic lottery winner who always looks perfect and I'm a hot mess. I know it can be tempting to always say "you look great!" or the other classic "you always look beautiful to me" but at least pair that with something honest. For example, "you always are beautiful, however you should feel comfortable so if you don't like it change". That's assuming it actually looks bad, if it really is in her head go ahead and tell her she looks hot. The problem with doing that all the time is when don't know when you mean it. If you save it for when you mean it, then it'll actually mean something and we'll appreciate it. Another one you can try (with caution, do not use if she is emotionally fragile) is "you look great, but maybe you're right and that isn't the most flattering color/cut/style. (Also note, only the advanced can say cut because if it isn't part of your normal vocabulary it will seem fake.) If she's trying it on in a dressing room you might be able to say wrong size. Most of the time that's okay, just make sure she isn't especially emotional first.
Another main reason we ask is because we're really asking can I buy new clothes without feeling guilty that I need to spend so much money because NOTHING FITS and I may have to redo my wardrobe again soon anyway? People grow and change and that means things stop fitting correctly and we need to buy new stuff. Sometimes it happens gradually and it isn't a big deal. Sometimes life just smacks us in the face and all at once nothing fits. This is an awful feeling so we don't want to add guilt on top of it by dropping tons of money on a new wardrobe (especially when we don't know how long those clothes will fit us). So we hope that instead of getting mad that we take so long getting ready because the outfit we planned on wearing no long even fits well enough to make it all the way on your body you'll realize we're hurting and suggest that we buy some new clothes we feel comfortable in. That would be so nice.
One of the main reasons we ask is because we want you to ell us we're still attractive. We're asking would you spot me at a party and want to date me? We want you to spend time looking at us, appreciating the effort we took to get ready and say "You look great!" and mean it. There is such a big difference between around the house messy hair and sweats and going out dolled up so when you say "you always look the same to me", it isn't quite the compliment you think it is. It means that spending time doing our hair, make up and choosing a nice outfit does is equivalent to how we look when we're in our old pajamas and haven't showered yet. Thanks. Ego boost. It's a good thing you always find us beautiful but make it a point that we look especially beautiful with that dress on. And go ahead and say it when we look a mess. That's great too. Just don't act like there is no difference. Because we work really freaking hard to make a difference. Notice it.
Next time the woman in your life asks how she looks in an outfit really look at her and understand where she's coming from so you can have the perfect compassionate response that makes her feel lucky to have you in her life.
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