How to Look Sharp While Dressing Casually

Last week, I wrote an article called “The Haute Écriture Gentleman’s Guide to Dressing Well” in which I explained the essentials to wearing formal menswear properly. Now, I’m going to give you a guide on how to look sharp while dressing casually. Casual wear usually isn’t about looking well dressed but it can be and it should be as you age. Follow these tips to make sure you always look your best for every occasion.

Wear Well-Fitting Clothes

I said this in the gentleman’s guide and I’ll say it in this guide, this is the most important tip on this list. You should always wear clothes that fit you well, even if you’re dressing casually. Your shirts should not be too long or short nor too wide or slim. The same thing goes for your pants. Clothes should compliment the shape of your body and the attractive attributes of them as well.

Again, there are some specifics we need to cover so let’s get a little more detailed.

Wear Slim-Straight and Straight Leg Jeans

The fit of your jeans is as important as the actual size. If you want to look sharp while still  wearing jeans, you need to get slim-straight jeans or straight leg jeans. These jeans work well because they aren’t to wide, nor to skinny. That also mean you shouldn’t wear skinny jeans or anything wider than classic fit jeans, like boot-cut jeans, unless your body type calls for it.

Read this guide here for more on jean cuts.

Quarter Breaks to Half Breaks Look Best

What is a break? As I said in my gentleman’s guide, breaks are the amount of creasing your pants get when your pant leg meets your shoe. While no breaks and a quarter break looks best for formal wear, quarter breaks to half breaks look best on jeans, khakis, chinos, and other types of casual pants. No breaks don’t look good here as having your pants cover your socks looks best for casual wear. Full breaks, however, always look bad regardless of whether you’re dressing formally or dressing casually. They will make you look sloppy.

Read this article here to see photos of different break types.

No Shirts With Large Logos

You know that shirt you got from American Eagle that says “American Eagle” in big letters across your chest? Get rid of it. The same goes for every graphic t-shirt you own. Throw them all out. Swap them for plain or stripped t-shirts instead with black, grey, and navy being your essentials. Why do you need to do this?

Logo t-shirts and graphic t-shirts are for teenagers — maybe college students but this is when you should start using tips from this guide — and wearing them will only make you look immature.

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Get Some Casual Leather Shoes

Invest in some oxfords, moccasins, and canvas or even perforated leather slip-ons. These shoes will make you look better dressed while still looking casual. You can wear formal leather shoes, too, with a pair of jeans for a casual-formal look as well. Regardless, you should wear leather shoes a lot more often and if not, canvas slip-ons. Dressing casually doesn’t always mean wearing sneakers.

No Ripped or Torn Clothing

Any pair of jeans or shirts you own that have any holes, rips, or tears in them should accompany your logo shirts in the trash. The same thing goes for cut-off shorts with threads hanging off of them.

Clothing like this basically does the same thing as logo shirts; they make you look immature, though, ripped clothing also does a little more and makes you look sloppy. So, just don’t wear them.

Wear Casual Button Up Shirts and Polos

Wearing a casual button up shirt will make you look well dressed without making you look formally dressed. This is because regular button up shirts are meant to be tucked in and are usually quite long while casual shirts are short enough so that you don’t have to tuck them in.

Polos will also make you look well dressed but since these come in varying lengths and don’t have separate formal and casual sections in stores like button up shirts do, they are a little more difficult to shop for. They still look good, though.

Wear Colors Well

The most important colors to have in your wardrobe are neutral colors like black, grey, and navy but you can and should have other colors to wear. When choosing a color, whether it’s for a t-shirt or a casual button up shirt, you should wear colors that compliment your skin tone.

Also, don’t wear loud, ostentatious colors. Wear something that can give an outfit character, but not make you look flashy. Try going for pastel colors when you first start looking for new clothes.

Those are my tips for how to look sharp while dressing casually. I know trying to follow all of these tips might be a little difficult at first but they won’t be after a while. The goal here is to wear clothes that make you look more mature and make you look like someone who wants to be respected and taken seriously. Following these tips will help you do that.

So, what do you think? Do you like these tips or are there any that I should’ve included for looking sharp while dressing casually? Let me know in the comments below. Also, don’t forget to subscribe to get new posts sent directly to your inbox and follow me on Facebook, Instagram, and Snapchat.


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