How to Look Stylish in Men’s Casual Wear

Wearing men’s casual wear doesn’t mean looking sloppy or underdressed.

In fact, you can style your casual wardrobe so that you look sharp and ready to make a good impression. You never know who you’ll run into while running errands at the weekend or going for a casual outing after work, so dressing stylishly is a valuable skill.

It’s not that you always need to be in the latest fashions from a magazine, in fact, it’s often better to stick with classic styling that gives a more timeless look. You can pull off casual-yet-stylish, and here’s how:

Start with basic bottoms

Looking stylish in casual clothing means you have to dress on the smart end of casual, rather than getting around in old sweat pants. You want to have a bit of polish about your look.

We would start with three pairs of basic bottoms. First of all, a good pair of wool trousers. Heading into fall, you’ll find wool a warmer option and you’ll appreciate its wrinkle resistant qualities. A good pair of wool trousers that are fitted to your body shape can take you from dress casual to a night out without looking rumpled. Choose a dark color to go with most top combinations.

Secondly, a pair of cotton pants with quarter top pockets are also good for dress casual wear. These types of pants are comfortable, especially if they are blended with stretch to help the trimmer models look wrinkle-free. These Brax Kapok and Cotton trousers are a good example and available in several colors.

Your third pair of basic bottoms should be a good pair of jeans for more casual outings or events. A darker wash tends to be better for giving you the ability to dress up or down.

One of the real keys to looking sharp in jeans is to choose the right fit. Slimmer fits tend to be more flattering and look more put-together than a baggy pair with cuffs dragging on the ground.  That doesn’t mean everyone should buy “skinny” jeans – this is a fit that won’t suit all. However, tailoring jeans to suit your body shape will be worth the investment.

There are three pairs of basic bottoms for a man’s casual wear wardrobe Share on X

Have a selection of shirts

We would have three or four shirts that you can switch in and out depending on the occasion and the look that you’d like to achieve. Here are a few pointers:

• Dress shirt – You can wear your dress shirt as part of a casual outfit if paired with jeans to go out to a restaurant or with your pants for a dress casual look. Look for shirts with smaller patterns or in solid colors. Cotton is a good, breathable choice for any season.
• Casual or sports shirts. You might have plaids, stripes, patterns or solids. Fabrics can include things like twill, cotton or denim. The key thing for looking good is the fit. Your shirt should fit you well and comfortably trim.

• T-shirts and henleys. Cotton t-shirts and henleys that fit well and come in plain colors are usually best. It’s a matter of opinion, but graphic t-shirts tend to give a less “mature” look, while a plain, fitted shirt can look quite sophisticated. (See David Beckham’s ensemble below)

Jackets, sweaters and vests

A well-constructed sweater, vest or jacket can be the finishing touch for multiple outfits. Choosing the right outer layer can help your outfit to look more sophisticated, while maintaining a casual nature.

Layering adds interest and a new level of style to an outfit. You can layer your jacket or sweater over your casual shirt, or even layer two henleys, or a shirt over a t-shirt. Pay attention to those layers and make sure they fit well – this is how you can make an otherwise plain outfit pop.

Remember, you can also use your blazer or suit jacket to lift an outfit. Layering over jeans and a shirt immediately adds a touch of sophistication to your ensemble.

Here are some examples from our collections:

Footwear

If there’s one thing that can detract from an otherwise on-point outfit, it’s wearing the wrong footwear! If you want to look sharp in casual wear, then you need to pay attention to what you’re putting on your feet.

This rules out dirty old sneakers or anything that looks unkempt. A nice, plain, clean pair of sneakers can work well (see again David Beckham’s outfit further up). They are casually understated but help to enhance the outfit.

One option that you will find yourself wearing often is a nice pair of brown leather shoes. These might be in any of multiple styles; ankle boots, desert boots, loafers, boat shoes or oxfords. The point is they can elevate your casual outfit – try pairing them with dark jeans and a layered henley.

Red Wing Heritage Weekender Chukka

Accessories

Just like layering your outfit, accessories can add interest and sophistication. The key is not to overdo it. Simple is best! If you’re not sure, we would add one well-chosen accessory to your outfit and leave it at that.

For example you might add:

• A scarf
• A hat or beanie
• A wrist watch
• Pocket square
• Belt
• Bow tie
• Colorful socks.

Choose accessories that complement what you are wearing in terms of colors or patterns. For example if you’re selecting a scarf to purchase, choose one that will go with most of your casual ensembles.

Putting your outfit together

Everything must be selected with color, texture and pattern in mind. We lean toward plain and dark-colored pants because you will easily be able to mix and match tops of different colors and textures, making a few pieces coordinate with multiple options.

A few tips:

• Different colors look better on different skin tones and hair colors. Learn about the colors that suit you the best. When in doubt, most men look great in light blue shirts and these can coordinate with most pant shades.
• Once you have coordinated your colors, the next vital ingredient is the
  tailoring. An outfit is made or ruined if the pieces are not tailored for
  the individual’s body.
• You don’t actually need a wardrobe overstuffed with different casual options if you choose a few pieces wisely. Look for items you can mix and match.
• For the most part, ignore “what’s hot” from the catwalk this season. Fashion comes and goes, often with some dubious choices that won’t suit the regular guy on the street. If you stick with simple classics, you can easily make them more interesting with accessories.
• How do you avoid looking sloppy if you’d like to wear something like a hoodie? Pair it with something sleek, like well-fitted jeans. This is a rule that you can often apply generally; if your bottoms are a looser fit, then a more fitted top will help you to look more sophisticated.
• Wear socks! Some advice of late has made socks optional, even with a business casual outfit. However, wearing socks just looks more put-together and helps keep your shoes in better condition.

Final thoughts

If you’re ready to rock some fall style in your casual wear, then start by taking a look at your wardrobe and seeing what you have that will mix and match together.

For a polished look, the most important thing is fit. A few high-quality, well-fitted pieces will give you options that always keep you looking good. See your tailor for advice on fit and styles that will suit you.