If you’re going out on a date with a woman, dress like a man.
Dress in a manner that she understands you take her seriously, that this date could lead to the biggest commitment of your what to wear on a date in the winter lives. Because it just might.
Every married man can tell you that the relationship with his wife started somewhere — that there was a point when he decided to take a chance with this woman and see if they were compatible for the long run.
Note: this isn’t an article about how to dress when you’re hanging out with or meeting with a group of female friends.
The focus here is how to properly present yourself to a woman that could very well be your life partner.
If you’re confused as to the difference, read this classic AOM article: “Stop Hanging Out With Women and Start Dating Them.”
Why dress sharp on a first date?
- Physical attraction matters — Simply put, women care about appearances and are drawn to healthy, attractive looking men. Clothing covers 90% of your body — if worn correctly it can help you look better by strengthening your positive features and minimizing your less than attractive ones.
- Dressing sharp for another shows respect — You can’t control whether the woman you’ll be meeting will like your personality; you can, however, make a conscious decision to take the time to look your best. She’ll be spending a lot of time making sure she is presentable and dressed for a fun time — the least you can do is return the favor. It’s simply a matter of treating another human being as you would like to be treated.
- Dressing well indicates you have social skills, as it makes socializing easier — Women look at not only the way we interact with them, but the way we interact with others. Our ability to socialize is an indicator of our ability (or inability) to negotiate in a community where resources are scarce. When you meet her friends or family, is the impression positive? With little else to go by, your appearance is going to play a larger role than normal. By looking sharp and simply smiling and nodding politely, you’ll be amazed at how most people will form a positive impression.
- Dressing sharp puts you in the right state of mind — When you wear a uniform, whether it be for sport or work, the clothing helps you focus on the task at hand. The same thing is true when you prepare and dress sharp for a date — from the shower and grooming to making sure your clothing is clean and in good order, getting ready is a time for reflection on what you’re about to get yourself into. Give yourself the time to prepare, and wear clothing you’re confident in. You’ll find these two preparation steps get your date off on the right foot.
- It brings your face into focus — Wearing the right clothing keeps your date’s attention on your face. Like a well-proportioned picture frame it shouldn’t overpower or detract from its purpose of placing you in the best light. Avoid flashy accessories or clothing that will draw too much attention to itself — this is a date, not a fashion show.
- The right clothing can exaggerate healthy masculine traits — Clothing like a sports jacket can exaggerate masculine features such as square lines in the face, broad shoulders, muscular chest, smaller stomach than upper torso. These are all things women are subconsciously attracted to — they signal a healthy level of testosterone. Although not the sole factor a woman should choose a husband on — it’s nice to start off on the right foot. An important point to note is that most of the time we judge attractiveness in a moving environment. We can spot a woman from a considerable distance by the way she moves her hips as she walks — we are attracted to this. In the same way women can spot a man based off the way he naturally moves his shoulders and arms. This is important as you’re sending a positive message of health before your face comes into focus.
- Your date is sizing you up — On a first date, both parties are looking each other over, searching for clues about their date’s personality and long-term potential. You only have a few hours together, so these clues will not only come from your conversation, but your non-verbal behavior as well. It’s all well and good to say you want your date to like you for you, but how will she ever get to know you if she turns down a second date? Be sure that how you dress sends the right signals and not only shows respect but reveals your personality.
Specific Dressing Guidelines
Casual dates, especially outdoor ones, allow a relaxed outfit but not a sloppy one. Even if you’re going to be engaged in a sporting activity, wear a respectable outfit that isn’t tattered or dated. Stay away from clothes that make it seem like you didn’t put any effort into dressing — plain blue jeans or work clothes look bad, as do sweatpants or athletic pants (unless it’s a jogging date). Dark-wash jeans in black or deep indigo strike a nice balance and can be paired with anything from a short-sleeved collared shirt to a dress shirt and sports jacket. Tuck in your shirt (unless your date is in Ocean Beach) and match a casual leather belt with a pair of similarly colored leather shoes. And leave the running shoes for when you are running.
Dinners dates and other evening events in an urban setting usually mean you should wear a jacket. For evenings or events that do not require a suit, look to a blazer jacket; if you’re going to be out during the day and want something more casual, a sport jacket is always a flattering option. And enough with the nonsense that you’ll be the only man wearing one — a jacket has time and time again been shown to help men look more masculine and authoritative. Plus, it provides ample pockets for carrying your first date supplies. If it gets too hot or you find the situation is more casual than expected, you can always discreetly take it off.
Event dates at a city theater or concert hall are a great way to ensure the clothing required is understood. Although you’ll be dressed-up for the occasion, there is less risk your date will be turned off by your appearance. Dust off a good suit and wear a clean, well-pressed shirt and tie. You can always slip the tie off when you go for drinks afterwards if it seems a little too stuffy.
No matter how informal the date is, pay attention to your shoes — Whether you are wearing canvas sneakers for your walking tour around San Francisco or dress loafers for your dinner at Truluck’s in Austin — you can bet she’ll look to see what you’re wearing. Shoes say a lot about you and are one of those aforementioned clues to your personality that your date will check out. Ensure your footwear is clean, functional, and stylish.
Grooming Tips for a First Date
Hair — Never try something new with your hair right before a date — this advice is for the hair on your head, face, and anywhere else for that reason. Instead, go with the grooming routine that’s worked for you; after all, she agreed to go out with you based off what she’s seen of you before. Get your hair trimmed the week before your date and use the same barber you always do.
For more on how to take care of your hair, visit these classic AOM articles: How to Ask for the Perfect Haircut, Your Grandfather’s Hair Products, and Hairstyles for Balding Men
Cologne — Despite what the human pheromone peddlers in the back of men’s magazines may say, there is no magic cologne or scent out there that is going to have angels falling from the sky. There are certain odors that under specific conditions can — when a woman is receptive — increase her attraction to a man. But the factors involved are many – -and you are much more likely to repel a woman if you try to manipulate this or if you come off as trying too hard. Instead, focus on simply being clean and if you wear anything — bay rum aftershave or a cologne — wear it very conservatively. Think if you were close to your date in a closed room — she should at most just be able to smell you. More than that and you’ll have her wanting to roll down the windows to breathe.
Grooming details — Clean fingernails, trimmed nose hairs and the tuft of hair growing on the back of your neck — take care of them. Let me be clear — I’m not advocating a wax job on your chest hair. I’m simply saying be well groomed and clean — these little things matter, especially if you expect her to want to get close to you.
Dressing Sharp for a Date on a Budget
You don’t have to spend a fortune to look like a million dollars. Just look at Will over at the Houndstooth Kid for inspiration on dressing sharp on a budget.
Thrift stores and gently used secondhand clothing are options. There’s been a bit of a revival in shopping at secondhand shops, but the deals are still there. The key is you have to have the time to do it — expect to wade through a lot of junk before finding that one piece of clothing that makes the time spent worth it. Also, because most men shopping at thrift stores don’t have much need for dress clothing, it’s easy to pick up a good suit coat or two for casual jackets. Take them to the cleaners and have them altered to fit better as well. With an adjustment to the sleeve length and a bringing in at the waist — that jacket can look better at than the one you saw on sale at a department store for 0.
The time to shop for clothes is well before the date materializes. Have a couple of go-to first date outfits at the ready in your closet. When a first date opportunity presents itself, you don’t want to be running to all the thrift stores in town, scrounging for something to wear.
Ensure your clothing is interchangeable. Classic clothing used to build a flexible men’s wardrobe is always worth spending money on over a fashion piece that only works with one other item in your wardrobe. You’ll get more mileage out of a light blue dress shirt with a slight pattern than a bright blue one with a graphic design printed on the front. A couple sport jackets, a few pairs of interchangeable trousers and jeans, mixed with half a dozen classic shirts can easily yield more than 50 outfit combinations.
Wear a stylish accessory. A small stylish detail like a pocket square in your jacket breast pocket, a boutonniere on your lapel, or a quality watch on your arm can elevate your style in the eyes of a woman because it shows you pay attention to the details. Jewelry on a man is a balancing act — I prefer pieces that have meaning to the wearer (these have the additional benefit of being potential conversation starters), but I have to admit the men here have a swagger than enables them to pull this off.
But keep in mind what we said at the outset about the importance of nonverbal clues. If something like a boutonniere isn’t true to your personality, skip it.
Know when to spend, and know when to keep the wallet closed. Barron Cuadro does a great job breaking out his assessment of where a man should spend his limited resources and where he should skimp on his wardrobe.
Be Prepared and Be Considerate
You want to be prepared for the specific date you’re going on — unless it’s a surprise, you should know the itinerary and dress for the occasion. If you’re hiking through a park for a picnic you’ll want a different style of clothing than you would for an evening at a nice restaurant.
And make sure your date knows the plan as well — a woman wearing heels isn’t going to be happy about your last-minute decision to walk around a wet park. It sounds obvious, but it’s not always that simple. Taking her to a Vegas show? If it’s the Blue Man Group, be careful as there is a reason they hand out rain suits to those sitting in the first few rows. Trying to get into a trendy nightclub after dinner? Make sure she has a jacket or you have one to lend her if you end up waiting in line for an hour.
It’s not about whether or not she’s a good sport, it’s about you thinking of others instead of only yourself. I haven’t met a woman yet who doesn’t appreciate a considerate man.
Finally, remember that clothes are crucial but can only get your foot in the door. Be sure to show your manners, have a sense of humor, and fill the date with engaging conversation. The funny, interesting gentleman in nondescript duds will win the day against a uncouth boor dressed to the nines.
A man going on a first date should ensure he is well groomed, dressed sharp, and then he should forget about his appearance and have a great time. The sole purpose of all this proper dressing talk is to give you the confidence to focus on the woman you’re with.
Best of luck to you.
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