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“Dress Me Like the Man You Want to Be Seen With” – by Matt M.

Every girl’s crazy about a sharp-dressed man, of course, and coaches such as Jack and Scott M. have noted the importance of dressing up, with all the confidence and self-realization it can bring. What better way is there to show off your personal improvement than with a new wardrobe?

A good wardrobe goes even further than that, though, in that it’s cyclical—the better you feel, the more you want to dress up to match that inner confidence with outer threads, and the more compliments and positive female attention you get from those threads, the more your inner confidence increases. It’s an upward spiral, and for those who’ve experienced it, it’s quite a thrill. Relatedly, there’s a workplace correspondence, in that the better you show up to work, the more likely you are to stand out, get the attention of the right person, achieve the promotion, or gain the self-confidence to realize you can do better than this dead-end job. The best part is you already have a closet full of interview-ready duds.

But we’re here to talk about dating, and there are fewer better venues for showing off your new wardrobe than on dates, which match the sense of excitement and anticipation with the readiness you want to evoke—in other words, the better you look, the less nervous you’ll be. Take the time to go to a tailor, get measured, and get familiar with the word “bespoke”—all of these are worthwhile investments. Websites such as Bombfell and Proper Cloth also allow you to do your own tailoring, some with trial-and-error approaches, others with body-specific specialization.

The best way, though, to fill out your wardrobe is to take a woman with you. Every woman I’ve ever dated has had a stronger, more innate sense of fashion, a finger on the pulse, and an eye for complementarity, than anything I’d be able to come up with. One of the best things you can tell a woman is “I want you to dress me like the man you want to be seen with.”

This may strike some as not decisive enough, putting the burden of decision on the woman, which reverses the masculine and feminine polarities. But it’s actually a very clear, direct statement of intention—notice that’s it not a question; it’s not “Do you want to go to the store with me to try on some clothes?” (It’s hard to read that in anything other than a nasal whine.) What you’re actually doing is swallowing your pride, affording her expertise and style the consideration it deserves and allowing her to make you an object of envy. There are fewer things better for a woman than to be able to point across a cocktail party and say, “That one? He’s mine,” and so think of how much stronger those words land when she’s engineered the look that one is wearing.

It’s important to note that this doesn’t mean you idly make the suggestion or say it in a passing-the-buck way. When you tell her to dress you like the man she wants to be seen with, it’s a declarative sentence, a subtle command, and one that needs to be matched with a time and place to do so—a date to prepare for future dates. Most women will jump at this opportunity, and meanwhile, you’ll save yourself the time and trouble of trying to decipher what looks good and what goes best with what. I’m colorblind, so utterly hopeless at any form of matching, but even a tailor may have a vested interest in selling you the more expensive outfit instead of the one that’s best for you.

Instead, appoint a date to be your style guide. This shows you inherently value her judgment, admire her sense of style, and are man enough to know when to delegate the decision. It’s win/win all around.

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