Sloppy to Sexy: Tips for Men to Look Their Best in Casual Wear

Too often guys get tied up on the assumption that looking their best requires them to go the whole nine yards with a suit, tie, uncomfortable shoes and all sorts of other formal wear options. Naturally, this causes many to simply go in the opposite direction and dress down – waaaaaaaaaay down. Like, all-the-way-to-sloppy down. However, neither too formal nor too causal will get you anywhere when compared with those who know how to dress casually but stay classy. If you want to look great, you're going to need to brush up on a little fashion sense. Follow these simple tips to get the most out of your closet the next time you're out with the guys or a special someone on the weekend.

Say No to Your Comfy Clothes

This phrase should be the cornerstone of your new fashion approach. Listen, it's no surprise your gym shorts and alumni shirt from 1999 are the most comfortable clothes you own; that's why they’re littered with holes, stains, and other scary signs of wear and tear. What might surprise you is that a nice pair of jeans and a smart-looking shirt can be just as comfortable, and they’ll give you the right look when you're out and about. Of course, there is a time and a place for your favorite clothes (ahem, at home in the man cave) just not when you're trying to look your best.

Pick a Shirt With Character

The shirt you wear can make or break your next casual outfit, so tread carefully when entering your closet. In an article released on the Men's Health website, Durand Guion, the men's fashion director at Macy's, offered some solid insight into the subject of going with a nice button-down shirt. In place of a T-shirt, having an appropriately colored button down can tie an outfit together and give you a clean, casual look. Just don't go with colors that are too dark unless you want to look like a lumberjack. Keep it light, fun, and casual with brighter colors or hip patterns, and you'll be well on your way to looking great, whether you’re at a family barbecue or at a trendy bar.

Pants Are Important, Too

Don’t forget about your pants – and not just for the obvious reasons. In many ways, this choice is just as important as picking the right shirt. Depending on how you want to present yourself, you have a couple of options. Your first choice is to go with some smart-looking khakis that compliment your button-down shirt. Just leave the pleat out of the equation. Instead, go with a flat-front style that keeps the look more young and modern. If you decide to stick with jeans, remember to leave all the embellishments and designs for your sister or girlfriend and go with a more traditional style that has a straight leg and darker rinse to avoid anything reminiscent of ’80s stonewash.

The Right Jacket

GQ magazine has a fun take on how to deal with colder temperatures, dressing up slightly, and the general jacket dilemma in this guide to casual wear. Basically, if you want to look your best while wearing a jacket, keep it simple by either going with a navy blazer, tweed sport coat, or corduroy jacket. With this arsenal of outerwear at your disposal, you can mix and match with your new favorite button down shirts, giving you some flexibility in your wardrobe while still keeping your style clean and casual. Avoiding outlandish combinations and matching colors will be your biggest obstacle, but as long as you know that mixing colors like lime green with your navy blazer isn't a good idea, you should be well on your way to looking great.

Putting Your Best Foot Forward

One of the final pieces of the puzzle centers around what you do with your shoes. Thankfully, this might be the easiest choice you face when setting up a new casual style. The biggest "don't" on the list is wearing worn-out sneakers or white tennis shoes. If possible, class it up a bit with bucks, boots, or even a simple pair of dressier leather shoes. Any of these options can keep your feet comfy without looking like you just walked off the court after a pick-up game    

Pulling It All Together

To round out the look, Esquire magazine offers some great tips in an article covering some of the details of a winning casual style. When purchasing a shirt, make sure it isn't too baggy or too tight. Instead, find a nice cut and fit that accommodates your shape and doesn't make your arms or torso look lost in a balloon of fabric. Additionally, if you're going to wear an undershirt, don't let it hang or stick out anywhere; that's not a flattering look. Finally, remember that whether to tuck in your shirt and expose your belt buckle depends entirely on the article of clothing in question. A good rule of thumb is that if it feels awkward when you tuck it in, chances are it looks awkward as well.

About the Author
Heather Stanford is a long time sales expert with a flair for fashion. She has worked in various retail environments, getting her start in a Men's Department in a well-known department store. She studied Creative Writing as well as Communications at the University of Central Florida, and has since become the company Blog Writer for Clothing Connection Online. She has a love for personal shopping, as well as a desire to make everyone look his best.