The Rules For Dressing Well

There are rules to dressing well. Of course, the rules vary by opinion and experience, and what works for one man might not work for another. The rules for dressing well are good suggestions and can be adjusted to suit you and your personal style. 


Whether you choose to bend the rules or not, but good advice shouldn’t be ignored. As menswear becomes more varied, experimental, and trendy, it can help to have some rules to fall back on when you feel overwhelmed by style and fashion. 

The rules for fashion are often rooted in history. They’re rules that have worked for generations, so it’s sensible to assume they’ll work today too. They often tend to be rooted in the obvious too. In fact, they’re so obvious that they’re often overlooked, such as rules around fit, quality, versatility, value, and a lack of extremes. 

Some of the rules you might have already discovered. Part of the fun of getting dressed, which no rules should spoil, is trying out new things, seeing what suits you, and how it makes you feel. However, these rules have stood the test of time for a reason, and when you use them well, they can act as a failsafe guide to help you dress well.

Wear A Suit Well

The key to a good suit is a good fit. If you’re buying a good suit off the rack, look for a good fit across the shoulders. It’s easier to have the chest and waist altered by a tailor than it is the shoulders. It’s wise not to wear a period suit unless you’re going for a complete period look. On its own, a period look will look out of place. Classic is the best way to go, and the most useful. Opt for a classic, like a dark, two-button, single-breasted suit with minimal details. A classic suit isn’t boring. It’s a uniform. Think of the suit as a canvas to build on. It’s the way you wear the suit that matters, not the label inside of it. 

Invest Wisely In A Watch

A watch can be like a piece of art. Choose a watch because you love it, not because you think it might make you money if you sell it on. Watches are very personal, but you also have to be practical. A functional sports model can go with anything and can stand up to being worn every day. A watch has to fit you too. It should feel comfortable and be the right size and depth relative to your wrist. Try the watch on before you decide to check the fit. 

Don’t Shy Away From Color

Don’t be afraid of wearing some color, either in your casual wear or formal wear. Many men are a bit scared of wearing color and feel intimated by wearing anything that isn’t black, gray, or navy.  However, color can be timeless and classic too. A green suit can look very stylish and fun. Pinks, greens, mustard, and brighter blues are all versatile colors that can be worn all year round and will give your entire outfit a boost. When it comes to wearing color, less is more. Add a bit of color with one garment or accessory. For example, add a men’s Balenciaga bag in a color to an otherwise plain outfit. 

Wear In Your Jeans

The most wearable cut for this incredibly popular piece of clothing is slim-tapered. This cut is a little wider in the thigh, which makes it comfortable to wear, but then narrows. A slim-tapered pair of jeans can be worn with either sneakers or smart shoes. It can be worn all year round, worn with anything, dressed up or dressed down. Wear dark, raw denim, and stay away from pre-distressed jeans. Denim ages with the way you wear it, which makes them yours and yours alone. 

Look After Your Appearance

This might be the advice that your mom gives you, but if you’ve spent money on your clothes, look after them. Use wooden hangers to hang your clothes, and store your best shoes on a shoe tree. After you’ve worn your suit, have it dry-cleaned and pressed. Wash your clothes regularly and don’t tumble dry them if you can avoid it, as this can degrade the fabric. Keep your shoes polished. Take care of yourself too. Make sure you have a simple grooming regime. Look after your skin, brush your hair, and keep your nails trimmed. These details will always make you look better, no matter what you wear. 

Keep Your Underwear Simple

Style isn’t only what everyone can see. When it comes to men’s underwear, there are two main rules that you should follow. If you’re an adult, stay away from novelty prints. Heavily branded underwear is also not very chic. Your underwear is a place where you can choose not to have any obvious randing. The style that has been around the longest is the cotton boxer shorts, because they stand up well to frequent washing, breathe well, and feel comfortable against your skin. 

Spend Money On Shoes

For a timeless look, look for a simple design. This is even more true for your shoes. The color, the pattern, and the sole should all be simple, and not too fussy. Anything that is too fussy might look good no, but it will date much faster than a simple style. A good quality shoe, especially one that you can have resoled, is the kind of clothing investment that can last a very long time, so you don’t want something that will look dated after only a few months of wear. You can wear good shoes for over a decade if you invest in the right ones. If you want to do this, choose a classic style, like brogues, loafers, or a plain, dark Derby with a round toe. The shape of the toe makes a lot of difference to how long a shoe stays in style. Round toes never go out of fashion, but pointy or square toes can look impractical and dated.