Websites including The Gentleman’s Gazette possess an encyclopedic amount of content on how to dress well, while thousands of images of iGents, dandies and influencers dance across Instagram feeds every day. Faced with all the content online, how do you know what suits you?
Those who are new to the game of classic men’s style can quickly become overwhelmed when trying to determine what they might like to wear. Even men who have been into classic style for years can fall into a rut. So, how do you go about discovering your personal style in the face of all the advice and information out there? Here are our top 10 tips.
1. Put Your Style into Words
If you’re reading this article, it’s established that you like to dress in a certain way, so you already have some sense of what you like and don’t like. Take out your favorite fountain pen and try writing it on paper (or just use your computer). Describe your style in a sentence or even a few words:
- How would you describe your ideal look? It might be “vintage academic” or “Italian sprezzatura,” but it could also be “put together” or “preppy.”
- What do you enjoy wearing? Do you do vests? Do you like bombers and safari jackets or prefer a regatta blazer?
- What are your strongest likes and dislikes?
- Who are your style icons? What do you like about their look?
2. Gather Inspiring Images
To help you describe your style, you can save images of styles, outfits, and pieces that you like. Pinterest is one of the largest social media sites in the world, behind only Facebook, Twitter, and LinkedIn and is the easiest way to do thisLinkedIn and is the easiest way to do this.
A set of Pinterest boards used to collect classic menswear images. Although it has a reputation for photos of craft projects and recipes, it is an easy way to capture and store images that you like related to classic men’s style.
If you have the Pinterest app on your phone, you can grab any image from any site and put it in your digital scrapbook or board. Looking at your pins will then not only help you remember clothes you want to buy but, viewed collectively, will give you a holistic sense of what your style is like. Of course, as you gather images, you may do so from other people’s Pinterest boards, which brings us to item 3.
3. Find Style Role Models (Plural) to Follow
As you go through social media, you’ll encounter numerous well-dressed gents whether on the number one source of online style inspiration–Instagram–on Tumblr microblogs or Pinterest boards. It’s important to realize though that even though you may like the personal style of someone with 15,000 Instagram followers, what he wears may not necessarily work on you.
The same goes for well-dressed men outside of social media whether Cary Grant to David Beckham or Idris Elba. You may be older or younger and have a different body type or skin tone, to name just a few things that can influence what looks best on a specific individual. However, with so many people posting to social media, odds are you will find somebody on Instagram with a body type or general appearance similar to yours.
Everyone’s style is really an amalgam of their influences, from family members to friends to celebrities and random strangers online. Along the same lines, the best approach with style icons is to take note of specific things you like from different people. It’s important not to imitate just one person because you risk coming across as a mere copy.
If you wear your watch over your sleeve cuffs, it’s obvious you are just copying Agnelli. You can admire the way Sven Raphael Schneider wears accessories like cufflinks, boutonnieres and pocket squares while also liking the contemporary urban edge of Dan Trepanier. You can love how Mark Cho effortlessly combines colors but realize the fuller cuts of his jackets is not for you. Pick and choose from the smorgasbord of influences with the understanding that you don’t need to be loyal to any one style guru.
4. Be True to Yourself
Even when you follow multiple influences, aim to be authentic. Do what’s true to you, not what’s popular. There are popular sprezzatura style choices seen everywhere online like keeping your button-down shirt collar unbuttoned or wearing the back blade of your necktie longer than the front and below your waistline. These are trendy, fashionable approaches that are more about uniformity than originality.
It can be tempting to buy tight suits, wear a suit jacket with sweatpants, or have your pants hemmed above your ankles because “everyone” is doing it in Suitsupply ads or photos from Pitti Uomo (and getting 2000 “likes”).
Unless this really makes you happy and is how you see your personal style, be cautious of following the crowd. The key is to be comfortable–both physically in the clothes you choose and the way you look. Dress for yourself, not for others.
5. Don’t Be Afraid to Experiment
To get to your personal style, there’s really no substitute for hands-on experimentation. If you see someone who wears an olive green linen jacket, you may want to try it yourself.
You can look at pictures all you want, but you won’t know whether you like pleated pants until you put them on. Though in theory, your rounded face shape would look better with a point collar shirt, you won’t know for sure until you wear one and compare it with a spread collar.
I tried point collars, cutaways, spreads, long points and button downs for shirt collars before settling on which I liked best. The first few years of my interest in menswear, I bought almost the full range of colors in sport coats, but since then I’ve boiled my favorites down to blues, browns, and beiges.
If possible, you can try things in boutiques and stores to see how you look at them. Alternatively, for pieces you aren’t too sure of, you can buy thrift or used. Yes, you will make mistakes and buy something experimental that you won’t like, but that’s what return policies are for.
If it takes you longer to figure out something is not for you, there’s always reseller markets like eBay or Grailed. Even if you sell at a loss, try not to look at it as wasted money. Instead, think of the journey as part of the reward. It’s like ordering a new kind of sushi or visiting a city you’ve never been to before. You’re in it for the experience, and there should be no regrets. It’s all part of the learning process.
6. Understand Your Physical Characteristics
One the reason we’re not into trends is that they rarely suit everyone. The skinny fit of suits today, for example, only works well for certain body types. If you want to capture your “own” style, it’s better to work with what you have rather than trying to conform to trends. Start by considering your body – your physique, your age, and your skin tone, for instance.
If you have pale skin, a dark navy shirt will wash you out. If you have brown skin, you can pull off more vibrant or hotter colors. If you’re over fifty, maybe slim fit trousers and a loafer without socks wouldn’t look best on you.
A mistake is trying to impose a style on yourself that doesn’t work for you just because you saw someone else do it online. The desire to wear anything you want is strong but not always possible. It’s a sign of stylistic maturity to realize that just because you admire how someone wore an item, it doesn’t mean you can or should wear it yourself.
7. Understand Your Environment
As you form your style, realize that it will be influenced by where you are situated. The way men dress on the internet often has very little to do with real life. What someone wears at Pitti Uomo or to sell a product is designed first to get attention in a medium full of so many competing images. Something may be photographed such a way to make it desirable, but ask yourself whether your personal environment would suit the style.
If you live in Manhattan, you may be able to wear suits most of the time if you want to, but if you’re in rural Kentucky, this stylistic choice will make you stick out like a sore thumb. If you’re in Italy, you can wear bright, fitted jackets that are at home there, but in London, they’ll look out of place. Realistically, part of your personal style–what you wear–is dictated by your environment.
This can be as basic as not wearing an elaborate pocket square because you are dressing for a conservative workplace or wearing sports coats and knit ties instead of suits and printed silk ties because you are never in a formal setting.
This may seem like it’s forcing you to compromise, but unless you want to march entirely to the beat of your own drum, you will have to fit your style to your milieu. Even within these limitations, you’ll still have a lot of possibilities.
8. Realize That You Can Have Multiple Styles
A further consolation is that you’re never really bound to a single authoritative “look”; the reality is that you’ll have multiple styles, and it would be rigid to assume that you need to wear the same sort of thing no matter where you go.
When you visit the countryside, you might wear sweaters and tattersall shirts with a Barbour jacket. When you’re taking a beach holiday, perhaps you’ll put on a linen shirt and espadrilles. You may still have certain common threads through all your looks–like always wearing a bit of blue–but odds are your style will really be multiple styles.
9. Assess Your Closet
Once you have accumulated a decent wardrobe, you can get to your core style by auditing and managing your wardrobe. If you have a social media presence or just for yourself, take a selfie when you wear something you think looks particularly good on you or that you get compliments on. When you have a bunch of photos, review them to see which pieces repeat the most often; these are the foundation of your personal style.
If we break it down, finding your style really comes in two major parts. The first is casting a wide net and trying a lot of things. The second is culling things you don’t ‘wear to get to a core wardrobe.
Besides looking at photos, look at your closet itself and get rid of things you haven’t worn for a long time, whether a certain number of months or a year max. If you don’t pick them, it’s a sign that they’re not your style. When you first start out, you’re enthusiastic and want to have more outfits, but eventually, you’ll reduce your choices and settle on a sort of uniform that represents you. For me, it’s sports coats and ties with interesting woven textures.
The more you try, the less you continue to experiment because you learn what does and doesn’t work for you and settle into “your style.” This can change depending on factors like age or weight, but for the most part, you engage in less trial and error.
This doesn’t mean that you have to stop adding to your wardrobe, though. If you find you like wearing navy wool trousers, you’ll soon want navy cotton pants, wool flannel, pleated and flat front, high rise and medium rise. The fact is if you’re serious about style, you’ll never want to stop working at it. The difference is that, after a time, you’ll buy from a more limited range of things because you know you look best in blue, that you prefer a spread collar shirt, and that you like an unlined tie.
As your eye develops, you can know at a glance whether an item you see is suitable for you. You’ll be more discerning and purge things from your closet that you no longer wear because they don’t fit your core style.
What you’re left with will include signature pieces that define you. I don’t mean something like Karl Lagerfield’s sunglasses and stiff collars or Pharell Williams’ hat–these are more celebrity costume than classic style–but your signature look may be a penchant for pocket squares, odd vests (meaning not part of a matching suit) or colorful shoelaces. Think of it as your brand in terms of style–an aspect that is recognizably and consistently you.
10. Know that it’s a Continuous Journey
Once you go down the rabbit-hole of traditional men’s style, you have a lifetime to enjoy the fruits of the hobby (obsession?), and even when you have a good sense of your style, things will not get stale.
If you relocate, change the sort of job you do, gain or lose weight or simply get older, your style will change in some way. When you reach a certain age, you may wear more comfortable or less showy clothes, probably of higher quality, but then again, you may always like a good Prince of Wales check.
A given is still that your style won’t (and shouldn’t) ever be static. I’ve shared some of the aspects of the journey you are likely to encounter but can tell you that there’s no substitute for experiencing it firsthand yourself. There will be errors and missteps, but this is part of the learning and the fun.