Just the Basics Ma'am: Date Outfits for Men
For most of us dating is a process with definite ebbs and flows; tedious and exhausting and at times exhilarating and fun. For those who have been out of the dating scene a while (you know who you are), dating can be nerve racking, prompting us to question, “Am I doing this right?” I had been out of the dating scene for nearly 20 years and found myself asking this question and plenty of other questions, such as, “WTF is happening right now?” Dating had changed significantly (which is a completely different series of blog posts for another time).
As a stylist, of course I noticed how men dressed for a date. Several dates mentioned to me that they were nervous about what to wear. They felt pressure to look ‘stylish.’ Most women expect their date to know the basics about styling themselves. Guys, chances are that your date is going to put (a lot of) thought into what she is going to wear, you should too. Putting thought and effort into your look will give you points right off the bat because it shows you care. Yeah, you want to look approachable- laid back even, but you also want to come across as “put together.”
What are the basics for dressing for a date so you look stylish and “put together?” I’ve created this post to take some of the guess work out of what I consider basic style rules that all men should know. This post is for all those guys getting back into dating or just wanting to be sure they’ve got, “just the basics.”
Just the basics ma’am
Dad jeans- You have heard the term before but do you know what “dad jeans” are? In general terms, dad jeans are ill-fitting jeans, typically saggy along the bum with a pool of material at the bottom of the pant leg. Jeans that are too short showing too much sock (white) can also be considered “dad jeans”.
Ideally, the bottom cuff of the jean should meet the top of the shoe, bottom of the ankle (similar to a “no break” in pants). This will show a little bit of sock-we will talk more about socks below. Alternatively, you can cuff your jeans, in a clean cuff that is anywhere between two to two and a half inches above the top of the shoe. Ankle boots look great with this look!
Jeans are not meant to fit like pants. Jeans should fit well, not too tight or loose and compliment the silhouette. They aren’t supposed to have an excess of material through the thigh and hip area, and sit lower along the waist, unlike suit pants. Jeans should fit more like a second skin-but not too tight! Most jeans these days have a certain amount of stretch (elastane, spandex, etc.) so it moves with you, unlike just denim that you must “break in.” A good staple jean to start with is the dark blue denim because it will go with almost any shoe you pair with it. Take time to find a pair of jeans that fit your body well, it is worth it. Lastly, great jeans tend to be pricey. If you like how they look and fit, you will get a lot of wear out of a great pair of jeans (an equitable ratio of cost per fit over time).
Socks and shoes situation- If you take care to wear nice (clean) shoes and appropriate socks, your date will definitely notice!! White socks should never be worn on a date. Sport socks should never be worn (i.e black ankle sport socks). Save the sport socks for athletic endeavors. There are a couple of different ways to pair your socks with your outfit. First, a general rule to adopt is that darker socks can go with darker shoes or lighter leather shoes (ie a light brown/walnut color). If you want to have a little bit of fun with your outfit, try wearing a colored, designed sock that complements the color you are wearing on top. This gives you a bit of an edge and personality. Second, you can also consider your pant color as a guiding force for what sock to wear. A good “safe” rule is, choose a sock that will match your pants or is a few shades off (i.e. kaki pant with kaki socks, grey pant with lighter grey sock). This uninterrupted flow of color makes your silhouette longer and you look taller.
Always have socks that go up to about mid-calf, you don’t want any skin showing between the pant leg and the shoe. Consider thinner dress socks, thicker socks may bunch up towards the top of the shoe, feeling bulky and will not look as clean.
It’s worth spending a little more on good shoes that will last over time and transition nicely from work to going out. A few good starter shoes are the: ankle boot, dress loafer, Brogue or Oxford. Ankle boots can be either a Chelsea (a pull on) or a lace up. Start with a black leather since it goes with everything and looks nice with jeans or chinos, and transitions nicely from day to evening. Dress loafers or Monk strapped shoes are a nice alternative for a slip-on shoe and are great for warmer weather. Again, they can be worn with chinos or jeans and, depending on the loafer, can go with a wool blend dress pant. Brogue or Oxford shoes are a nice, classic look that also transitions nicely from day to night. These shoes will pair with a nicer wool blend pant, jeans or chinos. If you are looking to buy a Brogue or Oxford, I’d start with a either a darker brown or a walnut color. For those of you who want to minimize your choices, consider looking for an ankle boot that has a Brogue toe cap; it’s very versatile and classy! For a more causal look, you should invest in either canvas or leather sneakers. You can wear both without socks and pairs nicely with shorts in warmer weather. Do not wear flip flops on a date-ever. No woman that you just met wants to see your toes, trust me on this.
Shorts and swimming trunks- Working with some of my male clients I’ve come to understand that there is a confusion between tight and fitted shorts. As a result, men tend to wear shorts that are too big and baggy which looks like they borrowed their older brothers shorts. What do I mean by too big? Well, a fitted pair of shorts should hit you in the right spots: length of short, comfortable waist, fits across the thigh and across your bum. Shorts showing signs of pulling along the seams would be considered too tight. The length of a fitted pair of shorts should fall no longer than two inches above the knee cap. Shorts that fall at or past the kneecap can make you look shorter. Refrain from wearing your trusty cargo shorts that have stuck by you since the 90s (ah, the stories they could tell).
Shirts- I think it’s safe to say that most of you guys will not show up on a date donning a sports shirt, but just in case there is some ambiguity...read on.
For a first date, you can’t go wrong with wearing a (pressed) button down shirt. When wearing a button-down shirt, make sure the shirt fits in all the right places. Make sure it fits in the chest with no pulling. The buttons on your shirt shouldn’t look like they are hanging on for dear life, with one wrong move sending a button sailing across the room. If it pulls across the chest then go one size up. This rule is the same across the midsection- no flying buttons! However, when you size up, often this means that the shirt gets longer in the front and back. An untucked shirt should fall no longer than mid-zipper. If you raise your arms and your mid-section shows, size up; this goes for T-shirts, soft collar/polo-type shirts. Shirts with a straight hem on the bottom should never be tucked. Lastly, when going from work to out on a date, your shirt should remain tucked if it has been tucked all day. A shirt that’s been tucked all day will be ridiculously wrinkled and you will look sloppy if you untuck it for your date.
Blazer-A blazer is a nice touch because you can dress them up or down. Blazers go with jeans or fitted chinos and with either a T-shirt or a button down. Again, fit is key to a nice-looking blazer! The length of the blazer should go no further than mid zipper and covering your bum. If you are particularly tall, you can get away with the length going a little past the mid-point on the zipper. The sleeve should fit right below the wrist bone. The shoulder of your blazer should hit you just at the curve of where your arm begins and your shoulder ends. If the seam hits below your shoulder, the fit is too long and looks sloppy, while higher on the shoulder will look like you are wearing your kid’s jacket. The top button of the jacket should hit about an inch above the navel. Typically, your jacket will not be buttoned, however, if you button it and it pulls, across the midsection it’s too tight and you should size up. If you aren’t someone that is considered, ‘off the rack’, you need to have your blazer, shirt, and pants tailored to look good. Its worth the extra effort.
No edge-Your date is going to look to see if you have any ‘flare.’ While this can seem ambiguous, subtleties that set you apart will not be lost on her. Your date will notice if you are wearing a jacket on trend (i.e. bomber, tweed blazer) or jeans that are black, not a standard blue. Something small, like cool socks may not seem edgy, but show you have a fun side. A man that has accessories sets himself apart every time- a scarf, bracelet, watch.
So, with "just the basics", you can feel confident, and with one less thing to think about on your date. Ultimately, chemistry and attraction is what warranted the initial date, but putting thought and effort into what you are wearing might give you the edge for that potential second date.
