One of the aspects of looking better and making yourself more attractive is your clothes. Not to put too fine a point on it but… frankly, men (and especially geeky guys) fall down rather frequently when it comes to dressing with any sense of style.
Not that I necessarily blame them, mind you. Fact of the matter is: style – like how to be more successful with women – is generally treated as something you should know instinctually rather than something you learn. The various examples and role models that most frequently cross our paths – men’s fashion magazines like Details or GQ, celebrities like Justin Timberlake or Johnny Depp – all either assume that you already know all of the basics and are ready for the advanced concepts or that you’re rich and classically good looking enough to just not give a fuck how you look.
As a result, most guys have no idea how to develop a sense of style and fashion outside of “Well, it’s clean and feels comfortable”.
Fortunately it’s not that hard to start building up a sense of style; you just need to know the basics of how to build a cool wardrobe. From there, it’s simple to put an awesome outfit together, whether it’s for work, play or a hot date.
Know How Your Clothes Are Supposed To Fit You.
I talk a lot about making sure that your clothes fit properly for a reason: because it’s the single most important aspect of clothes. There are three factors that will ultimately decide how your clothes look on you: material, quality and fit. Of these: fit is the single most important part. Material and quality will make a difference to be sure, but fit will transform you. A $200 suit from Banana Republic or Express that actually fits you properly will look immensely better than a $4000 Armani that’s sagging in the seat, puddling at your ankles and drooping off your shoulders. Unfortunately, we as a gender have lost track of how things are supposed to fit. We assume that certain styles of clothing are “uncomfortable” or that wearing over-sized clothes can hide the flaws of a less-than-perfect physique and, as a result, a large number of men wear clothes that are a size (or more) too large.
Clothes that fit properly are supposed to conform to the shape of your body. Most clothes – especially anything that you might wear to work or on a date – are not supposed to be so loose that you could play a pick-up game of basketball while wearing them. Loose fitting clothes are great for relaxing, working around the house or playing sports. Clothes that fit the way they’re supposed to will actually support you.
So once again guys: here is how clothes are supposed to fit you.
- The shoulder seams of a shirt should fall where your clavicle meets your shoulder. If they fall any further out, it’s too large and looks like it’s falling off of you.
- A long-sleeved shirt’s cuff should end at your wrist, not the back of your hand.
- A short-sleeved shirt’s sleeves should stop mid-bicep. Any further and you look like you’re swimming in your shirt. Any higher and you look like you’re trying to sell tickets to the Gun Show.
- A collared shirt should fit comfortably around your neck, allowing for two fingers to slide between collar and neck with ease. Too loose and you look like you’re wearing a Cone of Shame. Too tight and you literally risk cutting off circulation to your brain; it’s entirely possible to pinch off your carotid artery with a shirt that’s too tight in the neck.
- Any shirt, casual or formal, should fit close to your torso without too much material on the sides. A buttoned shirt should fit snugly around your chest without looking stretched. If it balloons out when tucked into your pants, it’s too big.
- If a shirt is meant to be worn untucked, it will have a square hem and come to the level of your belt. If it’s meant to be worn tucked in, it will reach down to your ass.
- Pants should sit at your natural waist – three fingers-width below your navel – without sliding down over your hips. They should be snug in the seat without being skin-tight or feeling as though they’re going to split if you bend over.
- Pant legs should be slim, not too wide or too tight. Wide pants will make you look like you’ve got sausages for legs. Unless you’re heroin-thin, avoid skinny pants.
- The cuff should come down to the top of your shoes, forming a natural crease called a “break”. The size of the break – the depth of the crease and how far the pants drape down the back of your shoe – varies depending on style and type of pant. You never want more than one break; it’s a sign that your pants are too long.
While we’re talking about fit: never underestimate the value of a tailor. Many department stores – Nordstrom and Banana Republic, for example – offer low-cost or even free basic tailoring with your purchase. Most dry cleaners can also do basic alterations for a nominal fee. An independent tailor, however, can be your best friend. Most cost less than you would think and can alter your clothes – including shirts and jeans – to fit you perfectly. Do your research, check Yelp, and find out their prices in advance, then include the price of tailoring in the cost of an individual item of clothing.
Perform A Stalinist Purge Of Your Closet
Now that we’ve covered how your clothes are supposed to fit, it’s time to put that knowledge to practical use: by clearing out all of the dead weight in your closet.
If you’re the sort of person who’s having a hard time putting together a cool outfit, the odds are good that you have a closet full of regret and poor decisions at home. These are just cluttering up the landscape and taking up space that could be better spent on clothes you actually look good in. The best thing you can do: start performing a massive purge of everything in your closet. Start from the back and work your way forward. If it doesn’t fit properly – it’s too big or too small – it’s out. If it’s labeled “relaxed fit” – it goes. If you haven’t worn it in the last four months1 – it’s out. If it’s five years old or more… seriously consider tossing it anyway, especially if it doesn’t fit or you almost never wear it. If you got it for free at PAX or DragonCon: toss that shame-tarp into the trash where it belongs. If it looks even vaguely like Affliction or Ed Hardy… well, you might want to douse it with holy water and bury it at a crossroad, just to be sure.
If you have suits that no longer fit, then consider taking them to a consignment shop. Otherwise: take everything to your local Goodwill and donate it all to a worthy cause. Be sure to get a receipt; you can write off your donations at tax time.
Now if you’re like me, and I know I am, then odds are you’ve pared down your entire wardrobe by 50% or more. That’s ok. Think of it like a controlled burn instead of a forest fire; you’ve gotten rid of the ugly undergrowth and dead wood that was cluttering up your closet and clothing options. Now that you’ve cleared out all of that space, it’s time to start to slowly rebuild your wardrobe. Except this time you’re going to know what you’re doing.
Start With The Basics
When you’re trying to learn how to put together cool outfits, you want to start simply before you start trying to get very fashion forward. You wouldn’t expect your first karate lesson to teach you the dim mak; you start with the basics and build a strong foundation that will form the basis of everything you learn afterwards. So it goes with style; you want the basics of a strong wardrobe before you start getting concerned with sprezzatura and trying to imitate people you see on street-fashion blogs.
So here is what’s going to build the foundation of your wardrobe.
2 pairs of straight-leg, dark indigo jeans – raw denim, preferably.
2 white dress shirts
several pairs of black socks
1 pair of slacks or chinos
1 simple black belt
3 – 6 plain tees
2 dark ties
1 v-neck merino wool sweater
1 pair of good, black lace-up shoes
1 pair of sneakers (NOT athletic shoes- think Chuck Taylors, retro Adidas; simple and classic designs)
These will cover 90% of your clothing needs.
1 dark, medium weight suit
1 thin hoodie
1 slim cardigan
2 scarves – one for winter, one for fall/spring
1 slim leather jacket
1 pair of boots (Chelsea, Desert, etc.)
Stick to very basic colors: black, grey, dark blue and white. You want to keep things as simple as possible; thus no embroidered or silkscreened designs on the blazer, crazy studs or embossed leather on the shoes, no “pre-worn” holes in the jeans. You want to stick to the classics. We’ll get to the more unique pieces in a moment.
Shop Smart. Shop… S-Mart.
I won’t lie to you: this can get pretty pricy. Clothing is one area where the axiom “you get what you pay for” is especially true. Skimping on the cost of clothes means you’re going to get shoddier clothing. If money is tight, I recommend that you splurge on the jeans and black lace-ups; a good pair of shoes and high-quality jeans are like an investment – they last longer and actually improve with age. Cheap shoes and jeans will only fall apart, meaning that you’ll have to replace them more often, costing you more money in the long run. Also: women will notice your shoes. Women always notice a man’s shoes… and they will judge you for them.
Material makes a difference as well. Consider the difference in, say, ring-spun cotton in tee shirts versus the thick, coarse cotton that most nerdy tees are made of; one of these is softer, wears better and conforms to the body in more pleasing ways than the other. A fine wool suit is going to look and feel better than one that’s a wool/polyester blend. It’s a difference in quality… and unfortunately, quality costs.
Don’t think that you have to spend a lot of money to get these clothes; in fact, with some clever planning, you can get most of them for up to 40% off retail. First: know your sizes and cuts. Different design labels will fit differently; Naked And Famous will fit differently than Diesel jeans which are going to fit differently than Joe’s Jeans, which are going to fit differently than Lucky’s or Levi’s. American Apparel tees are cut differently than the Gap’s. Dress shirts from Express and H&M are going to fit differently than ones from Nordstrom’s men’s section. Shoes are especially tricky; no two size 8s are going to be exactly the same. The better you know how they’re going to fit you, the better prepared you are to find bargains. Take the time to go to the stores, try on the clothes and keep track of what fits and what doesn’t. Be especially sure to write down the specifics: style name, size, color, etc. Having as much specific information as possible will make this next part easier.
Once you know which brands you prefer and how they fit, it’s time to start looking for deals online. Pre-planning is vitally important if you’re going to be doing any online shopping; you don’t want to buy clothes blindly from online retailers and get stuck with a pile of poorly-fitting, ugly shirts and pants, no matter how generous the return policy is. Impulse shopping is a huge no-no when it comes to online shopping. The last thing you need is to be sitting on another pile of regret because you thought you could pull off an outfit that only looked good on the model.
Amazon and Zappos will be your best friends when it comes to online clothes shopping: they have most of the designer labels, and at considerably cheaper prices than in brick-and-mortar stores, as well as cheap (or even free) shipping. When in doubt, Zappos should be one of your first stops, especially for shoes.
If you’re interested in higher-end designer labels – your Diesels, John Varvatos, G-Star and the like, it’s worth subscribing to discount retailers like MyHabit and Gilt; both have daily sales of some of the top brands with impressively steep discounts. Other online retailers like eModa have regular sales, allowing you to buy designer clothes on the cheap. It can be worth taking the time to enter the specifics of a particular piece (“34 waist raw denim larkee jeans diesel”) into Google and comparing prices from the results that spring up.
Also: check for sales and discount programs at your brick-and-mortar stores.
Building Your Outfit
Now that you have your basics, it’s time to start putting them to work. The great thing about having these basics in these colors is that they mix and match almost effortlessly. They go with everything. You can combine these almost any way you can think of and have an outfit that works, dressing up or down as needed. They take the guesswork out of trying to put an outfit together; you don’t have to worry about whether one piece is going to clash with your outfit or whether a particular color works with your hair and skin-tone.
Here are the rules for building an outfit:
1. Consider The Destination – are you dressing for work, for a date, for getting a beer with friends on the weekend?
2. Consider the Weather – It should be obvious, but the weather is going to make a difference. You may look stylish as hell in your blazer, but if it’s humid and you’re spending any time outside, you’re going to look like you’ve gone swimming in it. Colder weather means that you’re going to layer more… but you can also express yourself with a carefully chosen scarf to go with your overcoat.
3. Pick one focus piece and build your outfit around it.
Start with something you like and want to wear: an awesome leather jacket, your favorite vintage concert tee. This is going to be the foundation of your outfit. The rest of your clothes should work around it to compliment it rather than overpowering it.
Say you’ve got a date for the weekend and you’ve made plans to go to a sushi-making class followed by drinks afterwards at a quiet bar. You want to have the right mix of “stylish” and comfortable, with enough flexibility that you’re not going to feel under-dressed but not showing up in a suit… and you’ve got this bad-ass leather bomber jacket that you’ve been dying to wear. You start there: your leather jacket is your focus piece. Since you want the right level of “dressy” mixed with comfort, you pick the white dress shirt, match it with dark jeans and either sneakers or boots. If you tend to go for a rocker or mod archetype, you might want to include a thin black tie.
If you’re going some place nice for dinner, start with the blazer, the v-neck sweater, a tee shirt, jeans and boots. You can dress down an outfit by pairing slacks or suit pants with a sweater and sneakers. You can dress up jeans with a blazer and tie and your nice black lace-ups. You can take a suit and pair it with a v-neck tee and sneakers for a more informal look that’s still stylish.
As much as it’s tempting to go the next level and try more and more experimental looks – layering up the jewelry, the artfully distressed blazer, the novelty belt-buckle, skinny jeans and a summer scarf – stick to simplicity at first until you have a firmer grasp on the looks that you like and – more importantly – look good on you and your persona. The great thing about simplicity is that it’s timeless. There is a reason why Chuck Taylors, for example, have barely changed since they were introduced in the 30s: it’s a very simple design that just works no matter what you pair them with.
Take some time to get comfortable with the basics as you start to find your personal sense of style.
Peacocking Vs. Conformity
One last issue about building a cool outfit: ever since Neil Strauss’ The Game went mainstream, the concept of “peacocking” has arisen whenever the topic of style2 and dating come up. The idea of peacocking is fairly simple: you dress in a more outré style in order to stand out from the crowd; since everybody else is dressed the same, you’re going to appear so different that you’re automatically going to seem cooler and more confident than everybody else.
The problem with this idea (other than the fact that “peacocking” has come to mean “dressing like a fetish shop had sex with a drag review and vomited all over you afterwards”) is that there’s “standing out” and then there’s “looking like a fucking idiot”. Standing out can be a good thing… as long as it’s congruent with where you are and the archetype you’re trying to embody. It’s easy to stand out; just show up at a bar in a balaclava or a knit panda mask3. Just because you’re standing out from the crowd doesn’t mean that you’re going to be getting positive attention. It’s better to aim to be just slightly cooler than everyone else. Stand out… but in a cool, stylish way that works with your environment and your identity. If everyone’s wearing t-shirts and ratty jeans, a well-fitting button-down shirt and raw denim jeans or a blazer and Chelsea boots puts you a step above them. If they’re wearing long-sleeve shirts and slacks, a suit paired with a concert tee helps take it to the next level while still maintaining your sense of style.
The problem is that too many people try to find that “cool” by overdoing things: taking that artfully distressed blazer and pairing it with a graphic tee and a crazy scarf and rock-star shoes with embossed crosses and brass studs… and as a result they look like they desperately want to be Russel Brand and are failing massively.
Cool isn’t an additive process; you can’t just layer on the”stylish” with “cool” accessories or outrageous pieces with the assumption that each one is +2 to Awesome (Bind On Equip). If you want to experiment with more unique looks or stylish outfits, remember the rules for building a cool outfit: pick one piece as the focus and let the rest of your outfit be built around it. Too much detail only serves to diffuse the effect by dispersing the focus and making you look like you’re trying too hard.
It’s the little things that help define a cool outfit. Build from the basics and you’ll make looking cool seem almost effortless.
Want specific fashion tips? Need a second (or third) opinion about an outfit? Join the Dr. NerdLove Forums and ask the Nerdlove community for some help!