How to Dress For the First 10 Significant Moments of Your Relationship

Image via Complex Original

What to wear: Something you feel comfortable in that reflects well upon who you are and how you want to be perceived as.

You should always be reasonably well-dressed, and here's why: You're giving off signals about yourself to everyone around you, and one of those people could be your future better-half.

You want to seem like yourself, and definitely someone that can be dated. It's unfair to tell someone: This is how you should dress all the time, so we'll leave this one up to your own interpretation. Just be conscious of the signals your clothing is telling people you're attracted to. If you shirt reads, "FUCK," there's a good chance they're not going to take you seriously.

What to wear: Gitman Vintage chambray shirt, Buy It Now at Unionmade, $245; Champ cologne, Buy It Now at Need Supply, $34; Selvedge dad jeans, Buy It Now at Gap, $98; Yuketen shoes, Buy It Now at End Clothing, $561

You got her digits, you've been talking, and you're finally taking her out. Besides worrying where you're going to go and say, your biggest dilemma is what you're going to wear. You definitely want to put your best look forward, but without looking like a try-hard.

Start with a spritz on a subtle cologne, and break out the patterned shirt you've been waiting to wear. Then put on the newest dad jeans that are perfectly faded, and the crepe-soled shoes that everyone always gives you compliments on. You'll be killing it, and your confidence will shine through.

What to wear: Trojan condoms, Buy It Now at Condom Depot, $3

You're finally there. You're having sex. There are a million ideas and thoughts going through your head right now. Why the fuck would one of them be about clothing? The only thing close to clothing you should be wearing right now is a Jimmyhat.

What to wear: Norse Projects bomber jacket, Buy It Now at Norse Store, $195; Cut and sew denim shirt, Buy It Now at ASOS, $54; Ruell & Ray canvas pants, Buy It Now at Art and Survival, $180; Converse sneakers, Buy It Now at Concepts, $90

If there's anyone who will plant a negative seed about you into your girlfriend's mind, it's her best friend. Meaning it's super important to get on her good side. You may think you're meeting her just to hang out, but she's judging you up and down. Simply put, you want to look like someone who has their shit together, but doesn't seem super square.

Try a simple piece of outerwear with an interesting shirt, a pair of canvas pants that wear well but look surprisingly dressed up, and a pair of next-level sneakers. It will be the perfect balance to win over her best friend's approval.

What to wear: Onia bathing suit, Buy It Now at Onia, $130; Gitman Brothers Vintage popover shirt, Buy It Now at Need Supply, $105; Shades of Grey by Micah Cohen sweatpants, Buy It Now at Shades of Grey by Micah Cohen, $179

A weekend trip is a huge moment for a new couple. You may have been able to survive brunch with her girls, but a weekend trip lasts much longer than two hours and you can't drown your sorrows in bottomless mimosas. For these few days, you're going to want to dress and be as relaxed as possible so that the two of you can bond over irie vibes, instead of stressing out over a flight delay.

That being said, this isn't spring break. Ratty tanks and extra-long surf trunks aren't going to cut it. Even if you have no intentions of swimming in the choppy ocean, you don't want to be mistaken for a sloppy surf-bum at the tiki bar. Use this as a chance to inject some crispiness into your vacay wardrobe, and the next first weekend getaway with the next girl will already be half taken care of.

What to wear: Tuxedo jacket, Buy It Now at J.Crew, $525; Tuxedo pants, Buy It Now at J.Crew, $265; Alden shoes, Buy It Now at Shoemart, $418

If you're single, you can chug Natty Ice with your boys on New Year's Eve until you pass out at 11:30 p.m. If you're in a relationship, things are going to be different. You might not own a tuxedo, but this a rare opportunity to wear one. Your girl is going to expect some really special shit, so pretend like you're in the Jay Z "Roc Boys" video and get dapper for this annual event. 

You're going to live like it's The Great Gatsby for one night; Make sure you dress the part. She's going to be wearing one of her fanciest dresses, so don't make her ashamed to be giving a midnight smooch to a dude in a graphic T-shirt and baggy pants.

What to wear: Oxford shirt, Buy It Now at J.Crew, $70; Levi's jeans, Buy It Now at Levi's, $129; Allen Edmonds shoes, Buy It Now at Nordstrom, $250

Meeting your girlfriend's parents for the first time is like a job interview, but you shouldn't come dressed in a suit and tie. Instead, you should be wearing things that are nice and simple while ready to discuss yourself and your future ambitions.

The focus is on you, not your clothes in this situation. You want to look friendly and like a normal dude, not like a steezy model who just jumped out of a lookbook. Opt for an oxford shirt, dark, straight-legged denim, and a pair of chukka boots that don't look like you're trying too hard.

What to wear: Casual blazer, Buy It Now at Club Monaco, $250; Chinos, Buy It Now at Uniqlo, $40; Our Legacy oxford shirt, Buy It Now at Cali Roots, $150, Cap-toe shoes, Buy It Now at L.L. Bean Signature, $179

Valentine's Day is corny, but it might still mean a lot to her. Like your V-day plans, your outfit should be respectful, in good taste, and representative of where you're taking her that evening (besides Pound Town). Try to class it up a bit but without putting on costume-like formalwear. Break out a blazer and dressy chambray shirt, a pair of chinos or dark denim, and give your sneakers a break and roll with a pair of cap-toe shoes.

What to wear: Crewneck sweatshirt, Buy It Now at Supreme, $136; T by Alexander Wang sweats, Buy It Now at Forward, $225; New Balance sneakers, Buy It Now at Bodega, $160; RAW 5-panel hat, Buy It Now at Brick Harbor, $36

Before you tell someone you love them, you're probably going to be super nervous. Sure, it should come naturally, but this is the make-or-break moment for your relationship. Don't be corny and have it all planned out, just go with the flow. Say it when you mean it. For the ocassion, you just want to be you, so wear an outfit that's a typical representation of your individual style.

What to wear: Grey suit, Buy It Now at Suit Supply, $639; White dress shirt, Buy It Now at Brooks Brothers, $65; Knit tie, Buy It Now at The Tie Bar, $15; Wingtip shoes, Buy It Now at Lands' End, $90

Congrats, you've been dating for a full year. Now, you know she's going to expect some over-the-top shit and your full dedication for celebrating this occasion. If you take her down the street to your favorite hole-in-the-wall restaurant and dress like a chill cozy boy, you might not make it any further past the one year mark.

Instead, you're gong to need to wear your "nice" stuff that she knows you don't break out that often. A suit is completely acceptable in this situation, but don't look like a peacock trying to stunt at Pitti Uomo. Wear something slim, and dress the look down a bit by going with a knit tie. It's the perfect accoutrement to your thought-out ensemble. Also, don't forget the flowers.