How To Dress Well

When it comes to men’s style, knowing how to dress is not just about having the right clothes. Dressing well is about how you wear your clothes, understanding the different ways you can combine pieces into outfits, and accessorizing your look to elevate your style. Learning to dress better is also a matter of finding the right fit, buying high-quality clothing, taking advantage of modern trends but mostly sticking to classic designs, and knowing when to wear casual and dressy outfits. Having a wardrobe that you can rely on to express yourself confidently is a tool that every man should have. Some men prefer to wear skinny jeans with a t-shirt and boots for a cool casual look, while other guys will style black dress pants with a white button-down shirt and a blazer for a fashionable aesthetic. If you’re looking to upgrade your wardrobe, there are a few basic fashion rules that determine how men should dress. To inspire you with ideas, we’ve compiled this guide on how to dress well. From shirts and pants to brands and trends, explore these fashion tips to find ways to dress better and look nice.

How To Dress Well

Your Personal Style

Dressing well does not mean the same thing for all men. What works for you will not work for every guy and vice versa. Before you start building your wardrobe, you need to define your personal style. Find what you are drawn to in men’s fashion by studying events like Pitti Uomo in Florence or Men’s Fashion Week in New York. Scroll through Pinterest, subscribe to men’s style magazines, or just get out in the nearest big city to people watch. However you do it, figure out what speaks to your personality, and experiment with it until you have begun to create your own style and outfit ideas.

Invest in Timeless Wardrobe Pieces

One of the paragons of modern style, Ryan Gosling says in Crazy, Stupid, Love that you can rebuild your entire wardrobe in about 16 pieces, and he is right. That is the great thing about men’s fashion: a few staples can be endlessly versatile. If you stick to pieces that never go out of style, you will have a stable base to build your wardrobe from. You should have a few basic well-fitting T-shirts, jeans that flatter you, chinos, and a few different sweaters. For more formal occasions, you will need dress shirts, a classic blazer, and a well-fitting navy suit. A few different simple sneakers, a pair of boots, and a sharp pair of leather dress shoes will round out your basics.

Find Your Fit

The single most important piece of menswear is the fit. Color, material, and details all come secondary to how your pieces fit. You can have amazing pieces from top brands, but if they do not fit, then you will never wear them well. Be sure to try on several different styles of pants and shirts to find out where you lie on the spectrum from straight, untailored fits to skinny cuts. Find what works well for your body so that you can use your clothes to present the best version of yourself. This will also be a part of your unique look; some people prefer a more classic look with looser fits, some will lean to skinny modern slim-fits.

Know Your Brands

Similar to finding your fit, knowing which brands complement your style will help you create a cohesive wardrobe. Try to find brands that reliably fit in your wardrobe on a budget and identify which men’s clothing brands you should invest in for pieces that will last you a lifetime. When looking to splurge on a higher-end piece, you do not necessarily need to look for statement pieces. Often, menswear is more expensive because clothing for men is made from higher-end materials with more durable construction and sharper details, so look for something you know will never go out of style that you can rock endlessly.

Tailor Your Clothes

Though we associate tailoring with suits, don’t be afraid to tailor all your clothing. Tailoring is a cost-effective way to personalize your wardrobe. You can find great classic pieces in thrift stores that may not have the modern fit that you want, but you can fix that with a trip to your tailor. Similarly, pants (even jeans) often require tailoring to get the perfect fit. Find a tailor you trust, and they can help make your wardrobe uniquely yours.

Dress For The Occasion

You should know what the dress code is before assembling an outfit for any event. Formal events typically require a suit, and you can lean on your tried and true navy suit. Black tie events normally necessitate a tuxedo. These events are rare nowadays, so it may be wise to rent tuxedos before you make a large investment in buying one. Business casual and smart casual can be achieved with basic pieces like chinos and Oxford-cloth button-downs. Whatever you do, just make sure that you prepare appropriately for the dress code.

Wear Classic Shirts

An array of classic shirts will help ensure that are prepared for any occasion. Aside from T-shirts, try a navy chambray or classic plaid flannel shirt for casual occasions. For semi-formal events or the office, opt for an Oxford-cloth button-down in white or powder blue. When getting dressed for more formal events, look for spread collar shirts in neutral shades that will pair well with your suit jacket or blazer. French-collared shirts can add some variety but are even more formal and are typically worn with traditional high-end business wear, so be careful that they match your style.

Dress shirts should be tailored so they hug your shape without being too tight and should not be loose enough to allow the shirt to billow out around your sides. With a selection of well-fitting shirts that can be worn for any occasion, you will always be well-dressed. Once you have mastered the basics, start looking at trendy riffs on classic patterns, such as the popover shirt or Oxfords with a banded collar. With so many different types of men’s shirts, there are a variety of styles for any look and event.

Buy A Blazer

Blazers offer a great middle-ground between your casual attire and more formal wear. Think of the blazer as your bridge between the two. A great blazer can be dressed up or down, depending on the time and place. Unlike a suit jacket, blazers are meant to be worn with mismatched trousers. Go for the ultra-modern look with a trim blazer, a plain T-shirt, slim pants, and sneakers, or go classic casual with dark denim and a sweater. Use your blazer as a layering piece in the winter by adding in a turtleneck or thick fisherman’s sweater underneath. Dress your blazer up with crisp chinos and a button-down shirt with a great pair of Oxfords. A few good blazers will allow you the ability to style your outfit for nearly any occasion in any season.

Find A Great Suit

Your first suit should last you a lifetime and be able to be worn in any formal occasion. The traditional advice is to invest in a quality, well-fitting navy suit. Some people will tell you to buy a black suit first, but navy is more versatile than black. Your first suit is an investment, so make sure to buy a timeless style made with high-quality materials and a tailored cut. Look for a classic two-button jacket with pants with a mild taper and a single break. Be sure to have it tailored so that the cut is exactly how you want it.

Shop For Quality Shoes

You should invest in your shoes because they will determine how well you execute your outfits as well as how you feel while doing so. Shoes should be comfortable without sacrificing your style. You should have one formal pair of shoes such as Oxfords that are quality leather. For casual events, a pair of white sneakers will work with almost every outfit. For everything in between, you can experiment. Chelsea boots are an on-trend option for semi-formal occasions, as are loafers. Brown shades like tan and stone will give you the latitude to wear these shoes with an array of outfits. Rely on old classics like desert boots and blucher moccasins for more casual looks that can also pull their weight in semi-formal outfits.

Take Care of Your Shoes

Because your shoes are investments that will help you look and feel good at the same time, make sure to take care of them. Learn how to condition and polish your leather shoes to add that finishing touch to your outfit and protect them from wear and tear. A shoe cleaning kit is a great tool to allow you to clean all your shoes and keep them looking fresh month after month.

Accessorize

Accessories can take your outfit to the next level if incorporated correctly. Buy accessories that you love so that you can wear them with every piece in your wardrobe. The essentials include a great watch and trendy sunglasses, but don’t be afraid to look into the smaller details. Try mixing in some fun socks with your formal wear to lighten the mood. Add a debonair pocket square to your suit to add some visual interest. Shop for ties that you love, whether they are classic varsity stripe ties, thick knits, or floral prints. If you wear French-cuffed shirts, you can always personalize your cuff links as well. There are dozens of small details that are chances for you to show your personality with your accessories.

Invest in a Nice Watch

A watch is a perfect way to refine and accessorize your style. Men’s watches come in many styles, so try different brands and types to fit your look and dress code. Try a chronometer with a NATO watch strap for a casual, everyday watch while a leather strap and clean face is classic for a formal watch.

Choose Sunglasses To Suit Your Face Shape

Sunglasses are a functional piece that can elevate a great outfit. Like anything else, they have to fit you right. Find sunglasses that work well with the natural shape of your face. Go online to find out what face shape you have. Whether it is square, round or oval, there are shades that will make your face shine. With that in mind, find sunglasses that complement the shape of your face first, then focus on the style. Before trying something flashy, buy a staple pair in black, brown, or tortoiseshell.

Wear A Belt

While dress pants and casual trousers should be fitted to your waist, certain men’s pant styles require a belt. In fact, if your suit pants or trousers have a belt, you should probably wear a belt. Guys should own a few quality belts to wear on any occasion. You should have leather belts to match all your leather shoes. For example, if you have a go-to pair of chocolate brown Oxfords, you need a chocolate brown belt to bring your outfit together. Beyond dressy belts that should be relatively slim and match your shoes, belts offer another avenue to customize your wardrobe. A natural leather belt is a great option to wear with jeans and chinos that will only look better as it ages.

Look After Your Appearance

Though they say that clothes make the man, it is also true that you need to take care of your hair and skin. You should wash and moisturize your face daily to keep your skin looking naturally healthy. Try mixing in a retinol product to your daily routine to improve the overall tone and tightness of your skin as you age.

You should also get a stylish men’s haircut at the barbershop so that your entire look comes across as fresh, clean-cut and trendy. The most popular hairstyles for men start with short hair on the sides and back with longer hair on top. You’ll want to ask your barber for a fade haircut or undercut to highlight your cool short or medium-length hairstyle.

Of course, you have the ability to control how you smell, so make sure to use it well. Wear understated but masculine scents for deodorant so that you smell clean and approachable without being overwhelming. Complement that with a great cologne for guys to make sure that you make an unforgettable impression.

How To Dress: Men’s Style Tips

• Dress better by filling your closet with classic shirts, pants, and shoe styles that are fashionable and versatile.
• When dressing up, the most important part to wearing a suit well is getting the right fit.
• Invest in a quality watch that fits your wrist and offer a balance between functionality and style.
• Always coordinate colors and patterns, but try to keep it simple, neutral, and universally-flattering.
• Spend money getting nice dress shoes that are comfortable and classy.
• Research men’s fashion brands to find affordable pieces that will create stylish outfits.