Improve Your Casual Wardrobe: 5 Tips

So, you’ve reached that point in life where you want to take your personal style up a notch. But where do you start?

When most guys think about dressing better, they talk about buying new suits and fancy ties and pocket squares. All those things are wonderful, but those upgrades don’t make much impact on the average man’s wardrobe.

You see, unless you wear a suit every day, improving your casual clothes will give you a much bigger bang for your buck.

As workplace dress codes have relaxed over the last few years, “business-casual” has become “casual-casual” in many industries: jeans, polos, even t-shirts. People who aren’t in customer-facing roles often dress the same at work as they would on the weekends.

So upgrading your casual clothes for work (or play) is a critical part of improving your overall personal style. With that in mind, here are 5 ways you can instantly improve your casual wardrobe:

This post is brought to you by The Samuel Hubbard Shoe Company, who crafts premium, comfortable, functional shoes from the finest leathers in the world.

1. Break Up With Your Logo Tees

The problem with most men and their casual clothes is not that they have bad taste—they just don’t pay much attention.

It’s like a wardrobe on autopilot.

You throw on some faded jeans and your favorite, well-worn t-shirt and get going. But the problem with wearing that t-shirt of your favorite band from high school is that you look like…well…like you’re still in high school.

It’s the same with with branded logo t-shirts. Get rid of the logo-wear. Now that you’re a man, you need to start building your own brand.

T-shirts by themselves are not bad, but think about swapping out your old t-shirts with some more versatile solid black or colored t-shirts. A high-quality t-shirt can be layered nicely with a v-neck sweater or a sport coat to add a pop of color to your casual outfit.

Also, think about rotating in some polo shirts. Sure, to some critics polo shirts say “country club.” But more than anything, they say “established,” “confident,” and “I am old enough to legally buy a drink.”

You might be thinking: but when I dress casually, I want to be comfortable. Well, there’s no reason you need to sacrifice comfort when you improve your casual clothes. If you’ve ever worn a perfectly fitted suit, you know that dressing well can be EXTREMELY comfortable.

Instead, think of these upgrades as ways of becoming more intentional about your casual clothes.

2. Take an Honest Look at Your Pants

For many guys, jeans are just a commodity: they simply exist. “As long as they cover my legs and butt, and the holes are…um…tasteful..then I can keep wearing them.”

But if you take a closer look, you’ll notice that many of us wear jeans well past their expiration (or maybe they were never good to begin with).

Take a brutally honest look at your jeans:

Are they too worn out and faded?
Do they sag in the rear and crotch area?
Are the legs too baggy or too long to the point that they get torn up when you walk?
Do they say “sophisticated professional jean” or “weekend dad jean”?

One of the cornerstone pieces of a great casual wardrobe is some good pairs of well-fitted dark wash jeans. By well-fitted I don’t mean skinny jeans. I mean that they look like they actually hug your body and they get rid of that “butt sag” we talked about a moment ago.

Dark jeans are wonderful because you can wear them casually with some oxfords and a nice solid t-shirt, polo or button-up sport shirt. Or you can add some brown wingtips and throw on a dress shirt and sport coat to take your casual look up a notch.

In addition to a few good pairs of jeans, mix in a pair of fitted chinos. For many guys, chinos are the new jean. Just like jeans, they can be effortlessly casual or easily dressed up with the right additions.

3. Reimagine Your Button-Up Shirts

One of the biggest signs of a casual wardrobe on autopilot is when your closet is a sea of plaid, checkers and stripes.

I swear, sometime around the late 90’s or early 2000’s it was like every man between the ages of 17 and 32 got a memo that said: just buy a bunch of colorful patterned shirts, and you’ll be golden. It became the unofficial uniform of the guy who didn’t want to think about style.

I don’t hate patterns by any means. I love them. But I’ve recognized that for many guys—myself in included—colorful, patterned shirts can become a style crutch. You know the ones that make you look like a brightly colored picnic table? Yeah, those.

Just like with your weekend wear—old jeans and a worn out t-shirt—the colorful patterned shirt becomes a go-to, where you don’t really think about it. You just throw it on, and you don’t really pay attention to the colors of your outfit or how everything goes together. And pretty soon, you find yourself in a style rut.

Challenge yourself to think about buying a few solid-color sportshirts or oxfords. Or go with smaller, more muted patterns like gingham (or even, GASP, stepping away from the tried-and-true button up and mixing in some henley pullovers). Visually, that may get rid of some of the busy-ness in your outfit and give you a more muted appearance, which can often translate into a more sophisticated look.

Beyond patterns (or the lack thereof), start thinking about:

Fit – As with your jeans, the fit of your shirt is uber important. Find shirts that hug your body but still give yourself room to move. As I’ve talked about before, if a shirt looks like you can comfortably hide a pineapple and a six-pack of rolling rock near your mid-section, then it’s too big.
Length – If you’re still wearing your button-up shirts untucked, that’s not necessarily bad. The danger is that if it’s too long then it may look like you’re wearing a dress—or like you borrowed your dad’s shirt. My basic rule is that if the shirt hangs down below your crotch, it’s probably too long to be worn untucked.

4. Stop Fighting the “Grownup Look” and Embrace the Casual Sport Coat

unstructured sport coat — Source: Neiman Marcus

One of the beautiful things about getting older is that you can start wearing “grownup” clothing, and guess what? It looks absolutely normal.

I went to public high school and wouldn’t have been caught dead wearing a sport coat or blazer to school, for fear that I’d get made fun of. But now that I’m a young professional in my 30’s, not only does it look appropriate…but I can actually ROCK a sport coat with a casual outfit. It just works.

Don’t be afraid to experiment with mixing in a sport coat now and then. The “unstructured” sport coat is a great place to start. Less formal than a normal sport coat, it can be a natural complement to your casual getup.

Rather than “dressing up” your casual outfit in an obvious way, it lends an air of refinement to your comfortable-casual look. You still look relaxed; now you just look relaxed in a more presentable way.

As you think about adding a sport coat and experimenting with other layers, refer back to these 3 great layering tips from Dappered:

Contrast is key – The basic idea is that when you have 2 or more items together, you want the eye to be able to distinguish them. If the colors are the same, vary the shades. If you have 2 patterns, vary the sizes.
Textures matter – As with colors and patterns, contrast is also important. In general, it’s best to go from heavier to lighter texture as the layers get closer to your body.
“Dress like a Thanksgiving Meal” – The outermost layer = think dependable, main course. The inner or smaller items = side dishes, where you can take risks with color and patterns.

5. Put Your Best Foot Forward

Finally, one of the quickest and best ways to upgrade your casual outfit is to take your footwear up a notch. Have you ever noticed how many women, immediately after meeting you, look at your shoes?

Why?

Because shoes tell a lot about a person. You can have a perfectly put-together outfit, but if your shoes look shabby or cheap (or worse: boring), that can sabotage your whole outfit.

Now that you’re moving away from choosing shirts on autopilot, try breaking out of your usual shoe routine. Rather than reaching for the dirty, old, worn out sneakers, complete your newly upgraded casual look with a pair of chukkas or desert boots.

Chukkas and desert boots are great because they’re relaxed enough for a Saturday outing, yet they’re sophisticated enough to be a natural pairing with your weekly office wear.

As with the other upgrades above, a smart-looking pair of casual shoes can make a huge difference in the message you send to those you meet. And there’s no reason you need to sacrifice comfort for appearances. In fact, the right pair can give you the feel of an athletic shoe with look of a classic leather shoe. Look for solid construction, high-quality leather, a good sole, and something you can feel comfortable walking and standing in.

Conclusion: Improve a Few Casual Items and Transform Your Style

Once you take care of these simple updates to your casual wardrobe, you’ll be amazed how much it will improve your overall style.

By focusing on these core staples above, you’ve addressed 80% of your “daily” wear. Especially if you’re among the many people who can now wear casual clothes at work.

Next challenge? What to do with all those phone numbers from the ladies, now that you look so good every day…