Straight men are not always experts at explaining to a woman how she should dress for an occasion. They don’t realize just how much information you need. If this will be a day into night thing, but it’s formal and outdoors, you need to know that so you can wear a fancy shawl to keep you warm but not take away from your look. A man would just tell you to, “Wear a jacket” not realizing you don’t just throw a leather jacket over an evening gown. Men don’t realize that we choose our shoes based on the ground we’ll be walking on. Literally: are we walking outside on the ground? We need to know because then we’re putting on wedges! But when a straight man is in charge of giving you the dress code, he probably won’t think of those things. He’ll just give you some vague directions that could mean anything at all. So here’s how to understand the dress code, based on your date’s explanation.
When he says, “Outdoorsy”
If you’re going to hike or do something active, he’ll tell you. So when he says outdoorsy, he means don’t wear something you don’t want to get ruined. You’ll likely be grilling, sitting on the ground, doing a mild hike to your destination and helping to set up a few things. So jeans, a t-shirt, a flannel and comfortable walking shoes are key. But you don’t need to put on your full hiking attire; you can still look cute.
When he says, “Totally casual”
When men say casual, they mean it. When women say it, they still mean, “But wear some jewelry and at least cute sandals.” When men say it that means the other women may literally be in their workout pants and sweatshirts. If you’re going to someone’s house for a brunch and he says it’s really casual, the hosts may be rolling out of bed and throwing bacon in a pan. You can dress as if you’re in your own home.
When he says, “Pretty fancy”
Men don’t say “black tie” or “cocktail attire” but that’s what they mean when they say “Pretty fancy.” Fancy is a catch-all term men use when they don’t know how to explain that you need to whip out your little black dress and your blingy jewelry.
When he says, “You can dress up if you want to”
If your guy says, “You can dress up if you want to” then dress up. This is what he says when he got orders from somebody else (possibly his buddy’s wife who is hosting you all) that people should look nice. By the time those orders reach you, they’ve turned into, “Dress up if you want.” But dress up.
When he says, “My parents are conservative”
A man is not going to tell you that his parents are conservative unless he absolutely has to aka when you’re going to meet them, and he doesn’t think you dress conservatively enough for them. And remember, your date likes looking at your butt in tight jeans so he only passes on this information when he absolutely has to. And when he passes it on, it’s time to put on a knee-length skirt and a button up with a cardigan.
When he says, “They’re really not formal people”
If your date says this, he is trying to tell you that if you dress up, you’ll make the other people you’re hanging out with feel uncomfortable—and possibly bad. He may have friends who always wear jeans unless they absolutely cannot. So wearing your sequin dress and clutch around them for dinner will make them feel bad.
When he tells you to, “Just wear some sneakers”
Men don’t really know what sneakers mean for women. But when they say this, they mean you’re going to be walking a lot on this outing. So don’t wear your Converse: where your workout shoes that have the good sole and the solid lift.
When he says, “I can’t wait to show you off to my friends”
Look hot. He wants you to bust out the goods. He’s not going to say that because he’ll feel like he’s flaunting you. But when your guy says he can’t wait to show you off to his friends, he’s hoping you put on an outfit that is just shy of club attire. He’s wrong: you probably shouldn’t wear a bandage dress to a mom and pop restaurant. But try to meet him somewhere in the middle.
When he says, “Just know they’ll be a lot of dudes there…”
Translation: this is an aggressive, testosterone-filled environment like a sports bar and he doesn’t want to worry about protecting you from creepy men all night. Translation of that translation: save the skin-tight skirt for another time.
When he says, “Wear something you’ll be comfortable in”
This probably means you’ll be tailgating or hanging in someone’s back yard all day. You might be sitting in old folding chairs, on the ground or in the back of a truck. It also means you might be moving locations a couple of times (as happens during a tail gate). Long story short: your date just doesn’t want you complaining that your shoes are pinching or you’re too cold.
When he says, “These friends are really down to earth, humble…”
Don’t wear your designer stuff. These friends might not have much money or if they do, they don’t like to flaunt it. If you have a tendency to wear either very eccentric or very expensive clothing, this isn’t the time to wear it.
When he says, “Wear something you can wear all day”
He’s probably planned one of those most complicated dates that start with a nature walk, move into lunch at some cute spot, wind into cocktails somewhere cutesy and ends up at a nice dinner. If you have cute flats that have support, it’s time to bring those out. Wear them with jeans a cute top and a fitted jacket that will keep you warm but not look too casual for dinner.
When he says, “Just dress cute—wear whatever you want”
These are the only clean and easy instructions you’ll get. Accept them as a gift! Wear some of his favorite items. Dress in the way that’s uniquely you. You probably aren’t going anywhere formal, nor are you hanging out with anyone he thinks you need to alter your look for (like conservative family).
When he tells you he has to wear a suit
Sometimes the only information your partner can gather is the fact that he has to wear a suit. If he tells you this, ask to see the suit. If it’s a fitted suit, you can wear a cocktail dress. If it’s more tuxedo style, you need to wear an evening gown.
When he says nothing at all, ask the other women
Some men can’t or won’t give you any information on what to wear. If you’re going out with another couple, or some of his family, just ask them directly what you’re supposed to wear. They understand your dilemma. You’ll even get points with his mom if you make the effort to ask her what to wear.