Bill's Conversational Musings

How to Clothes Shop with a Woman

Women window shopping

I frequently find myself in clothing retail stores. I'm usually shopping with my wife or grandmother. You can't help but notice the men who are there who don't want to be there. The stand in the isle staring off into space or browsing on their phones. You can sometimes find them sitting on those store benches they provide waiting and wishing they were somewhere else.

I am never bored; to be bored is an insult to one's self. - Jules Renard

I took it upon myself to figure out a way to not become somebody who is bored with the experience. I knew this was a problem I could solve and could actually walk away having a little fun too. I have found that if I turn the experience (not the person) into a technical problem that needs to be solved, it becomes a man vs. the elements pursuit almost.


The first thing you have to do is commit to the activity. If you are not committed to making this a positive event, it will show in your emotions and actions. Remember, if you agree to go, you are there for the duration. If she asks you for your opinion, you had better have an answer.

It also means doing things for her before she asks. Some examples included offering to hold her purse or carry her bags or search the other side of the rack for something. And because the process can be frustrating at times, it can also mean just standing off to the side while she searches for something she likes.

Who & What

If you are shopping with a woman, this is probably somebody you really care about. If so, from a style standpoint who is she? Is she somebody who likes to wear casual or sporty clothes? Is she the kind of person who likes to go out after work? Thinking about some of her personal traits will help in the selection process and shows you have been paying attention.

What has looked good on her in the past? What colors complement her skin tone? Each woman has a different color palette. The basic classifications are Winter, Spring, Summer and Fall and there are colors that go well with each. I won't go into details here, but if you have a natural tendency for accuracy, it might be something worth looking into and researching about.

Additionally women come in all shapes and sizes. Try to recall a particular outfit that complimented her figure. Was it high-waisted? Was it long or short? There are styles of all kinds that help compliment certain features and hide others. Knowing the answers to these questions will help find similar garments that will look good on her.

When & Where

If she is picking out an outfit for an event, when is it? Is it in the summer or winter? Is she just shopping to update her wardrobe, then perhaps suggest something new. If it is for an event, knowing when the event will occur will help in the decision making as far as type of fabrics and style choices.

Where is the event taking place? Are there travel requirements? Will there be time to change? Ask these questions, even if you think she already has the answers to them. This line of questioning can help spur other questions she may have not considered.

Other considerations could be what time of day or garment construction. Are the buttons sewn on well enough to last even after being cleaned? Does the fabric need to be breathable or wrinkle free?


What I have found is the lady will be somewhat amazed that I am showing genuine interest in what she wears and the time seems to fly by just a little faster. She might even suggest, on her own accord, that I can freely walk around and meet her back in an hour or so to surprise me on her decision.

When she asks something like, "Does this make me look fat?" you will be able to speak to what looks flattering on her rather than just trying to answer yes or no. You can offer honest yet complimenting opinions based on what you have learned about her and her style. And, yes, you will be asked.

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So, what do you think? Did I miss anything? Is any part unclear?

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