How to Look and Feel Stylish (for Men)

Co-authored by Kalee Hewlett

Last Updated: February 16, 2022

The poet Richard Eberhart said "Style is the perfection of a point of view." Those of us not on TV or in the magazines probably won't have the same point of view as those who are a part of that world--style is more than mimicking celebrities. Style is looking good while defining "good" yourself. Don't think trendy, think unique. Having and embracing your own style makes you one step closer to being the man you imagine yourself to be.^{[1]
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Part 1

Part 1 of 3:

Discovering Your Style

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Have a reference point. Think about your personal style icons: people you consider to be the height of style. Whether it's Kanye West, Ralph Lauren, James Dean, or Walt Whitman, try and wonder what they're trying to accomplish with their style. If it is truly "the perfection of a point of view," think what your icon's point of view might've been, and think about what your point of view might be. Whatever it is, let it guide you when you shop and dress.
- Consider how you'd like others to think of you, or your style. Is it classic? Do you aim to be an iconoclast? Style isn't dressing "well," or "fashionably," it's dressing for your character. There are no style "don'ts" and only really one style "do:" wear what you want, and own it.
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Dress to fit your lifestyle. If you're a high school student, it won't do to clothe yourself as a full English gentleman. If you're a construction worker, you'll need to leave the Armani for the weekend. Tailor your point of view to the life you lead in order to feel as stylish as you look, and to make your style a part of your everyday life. Playing the style peacock only feels as good as your life will allow; it won't feel great wearing your Bruno Maglis if you've got to stand all day as a cashier, for instance.
- If your school or work maintain a strict dress code, push it to its limits (accepting the risk, of course). In these situations, don't underestimate the power of style-through-detail: make unique choices wherever possible.
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Act your style. If you're sporting Gucci, don't act like a boozy frat boy. If you're channeling Kanye West, don't be afraid to loosen your gait and walk with a swagger. If your clothing echoes a certain point of view, allow your behavior to do the same. This is key to feeling stylish, as it completes the personal connection you've drawn between yourself and your outfit.
- Let your clothes inspire confidence. Do your best to transfer how you feel strutting in the mirror in the morning to how you feel going about your day, realizing that nothing's changed from being in front of that mirror to being at work, or school.^{[2]
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Part 2

Part 2 of 3:

Building Your Wardrobe

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Shop for outfits. Design your wardrobe (especially if on a budget) to have a lot of stuff that matches (or doesn't--if that's your style). Prepare your outfits the night before. Not only does this save time, it allows you to put more thought into what you're wearing, giving the impression that you're cool and composed in all decisions stylish.
- Know the color wheel. A quick Google search for matching colors and patterns will reveal all sorts of informative sources regarding how to match. Even if you're looking to dress against convention, it always helps to know what goes with what.
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Buy quality that lasts. If you can afford it, try and go in on some high quality (do your research) items which can serve as foundations for your wardrobe. Shoes should be on the top of this list; no other item in your wardrobe will be used as much with as much wear and tear.
- Be sure it fits. Most clothing stores (note: not stores that also sell clothes) will have staff trained to measure your size and help you pick out items to match. You could buy the most expensive clothing and it would still look awful if none of it fit.
- Don't skimp on underwear. It may be tempting to save money on the piece of clothing least seen, but good fitting, high quality underwear lasts long and contributes to well-fitting pants.
- If you can afford it, try and build a relationship with a reliable alterations tailor as well as dry cleaner. Having one or both goes a long way towards making quality clothing last as long as it can.
- Browse regularly, buy rarely. Always know what's available, whether in stores or in shops online. It helps to know all of your options before making a choice.
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Have foundation pieces. At the core of your wardrobe should be versatile pieces, available for many different occasions. This saves a tremendous amount of trouble when it comes to crafting your outfits, as beginning the process will be as simple as choosing a piece to build on.
- Own a pair of shoes for every occasion. This will probably mean at least three: one casual (not running shoes), one semi-formal, and one formal. For the latter two, try to have one brown pair and one black, this covers essentially 99% of possible outfits.
- Dark wash jeans are almost a must-have, as they go with a variety of outfits and occasions. Even for the semi-formal events, dark wash jeans can be paired with an image-less t-shirt and well-fitted suit jacket if you're looking for something simple, but tasteful.
- Have one white and one blue button-down shirt. Like the dark wash jeans, quality button-downs are a tremendously versatile item. While the obvious pairing is formal, with a suit jacket or sports coat, you could roll up the sleeves and wear them un-tucked with jeans or slacks.

Part 3

Part 3 of 3:

Impressing with Details

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Have a grooming regimen. The most important detail outside of your outfit will be how you handle your hygiene. It's not necessary to reach for the top shelf grooming items, despite many claims that you're soap ought to be as nice as your shoes. Find a set of products for your hair, face, and body that you feel comfortable with, and stick with them. Don't go more than two days without a shower, and try to be consistent no matter what your rhythm is.
- Keep a signature cologne. While it might be tempting to keep a menagerie of fine cologne, you only really need one. That way, others will grow to associate a particular scent--your scent--with your style, deepening your point of view.
- Have a devoted barber, and see them every 4-6 weeks. Avoid letting your hair grow out of its hair-do. While this might be considered stylishly unkempt, its usually just a sign you've gone too long without a trim. Be open with your barber about what you're trying to achieve with your cut--having one which matches your style really tends to bring an outfit together.
- Don't over-condition your hair. Unless you have very thick hair, you usually won't need to condition more than every other day. For those with thin hair, you might consider experimenting with losing the conditioner altogether.
- Maintain your facial hair. Whether you keep clean-shaven or wear a full beard, be sure to keep it in check. Avoid letting your mustache move past your lip line. Own a brush or comb to tame your beard every morning. If you just keep some light stubble, have an electric razor and try to never go 4-5 days without a trim. ^{[3]
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Accessorize your outfits. Particularly if you're going for a "classic" look (picture how Ryan Gosling dresses), it will be an interesting combination in your socks, or the look of your watch's wristband which will really "wow" people. Even if you're reaching for a hip-hop aesthetic, or a punk-rock look, it will be the additions to your clothes which bring the outfit home.
- There's a lot of options for watches. You could reach for the most expensive watches to go with your most formal outfits, but could also keep a variety of lower-cost watches on hand.
- Hats also afford for a lot of creativity. You can top a plain outfit with a bright baseball cap for some added flair. Fit is key here as well; nothing looks sillier than an over-sized hat.
- If you wear glasses, be sure to match them to the size of your face and features. Large frames for large faces; the bug-eyed glasses trend is a distinctly feminine one, so mismatched glasses usually has the effect of looking cartoonish.
- When it comes to jewelry, tread lightly. Conventional wisdom usually suggests that men abstain from wearing necklaces, and that if wearing a ring (it should really only be one) it ought to have a thick band and worn on the right ring finger. If the ring has a gem, it should be low and wide.
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Don't over-do it. Unfortunately we can't all be Johnny Depp, with his jewelry store's worth of ornamentation. Adding too much to your outfit will potentially blur your style's point of view and have you veering into "gimmick" territory. A single flourish--a pocket square, an extravagant necklace, a matching baseball cap--will usually do the trick.
- Similarly, avoid grooming to excess. For better or worse, men are usually associated with a least a hint of "rugged-ness," which is ruined by excessive grooming. Common mistakes include moisturizing too much (you shouldn't feel oily) and dousing yourself in too much cologne.^{[4]
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Expert Q&A

Question

How can I find my personal style?

Kalee Hewlett
Fashion Stylist
Kalee Hewlett is a Celebrity Stylist & Confidence Coach with almost two decades of experience helping clients build confidence and ‘dress for success.' She works with her clients to transform their sense of self 'from the inside out’ by merging her expertise in image consulting with Neuro-Linguistic Programming. Kalee’s work is rooted in science, style, and the understanding that ‘identity is destiny'. She uses her own methodology and Style To Success Strategy to create positive identity shifts. Kalee is a fashion TV host and appears regularly on QVC UK sharing her fashion expertise. She also was appointed as the head judge and host of Fashion One Network’s 6-part TV show 'Design Genius.’

Kalee Hewlett

Fashion Stylist

Expert Answer

Look for photos of looks you like online. Use Pinterest, Google, and Instagram to find outfits that inspire you.
Question

How do I impress people (especially girls)?

Community Answer

First of all, be confident. Girls can easily tell if you're nervous or reluctant. Be smart. You don't have to be a genius, but if you know the answer in class, raise your hand and speak up. Most importantly, be friendly and kind to everyone.
Question

How do I gradually change my style to look better while not being noticeable?

Community Answer

Change your style one piece at a time over a long period of time. Don't mention to anyone that you are changing your style.