Men’s Guide to Dressing Sharp

March 19, 2019 7 min read

Men's Guide to Dressing Sharp

Capturing a look that announces you just stepped off the pages of a magazine might not seem like an easy feat, but looking sharp isn’t all that difficult. Including some classic wearable and non-wearable pieces, investing in good tailoring and slipping on some stylish shoes can help you polish a look that can take you anywhere you want.

The following men’s dressing tips should get you started in the right direction by honing your wardrobe, and ultimately, your personal style. Sharp men’s fashion can make any man look good.

Include Some Timeless Pieces in Your Repertoire — Wearable and Non-Wearable

Timeless Fashion Pieces

Timeless style pieces never get old. Like a delicious fine wine, these pieces only get better with time (and good maintenance, of course). These reliable staples are ready to help you look your best when paired with other stylish pieces of your wardrobe. Clean out your closet and get reacquainted with some old buddies from decades past.

  • Deep Indigo Raw Denim Jeans:Unwashed, raw denim means that the dye for blue jeans hasn’t been “washed” away. The color remains a deep blue shade — almost like indigo. There are a couple of benefits in this: First, the cotton fiber will stay soft and malleable, shaping itself to your body shape uniquely. Second, over time, there will be worn, faded-looking lines on your jeans along with naturally occurring color striations near the thighs and knees that will give your jeans a unique, stylish look.
  • A Leather Jacket:A well-tailored leather jacket will wrinkle perfectly at its seams and joints. The leather will also become softer as the jacket starts to fit you better through the process of being “broken in,” very similarly to the way shoes are broken in by your feet. The coloring changes that occur at the collar, on the pockets, and on the elbow areas add rich character to this classic piece. A great leather jacket should last a very long time. If the liner gets a little ragged, there’s no harm in taking it to a tailor for a minor fix. Don’t hesitate to put on this jacket for a variety of different reasons — it can be as versatile as you'd like to make it.
  • A Pair of Canvas Athletic Shoes:Add a pop of artistic style with a pair of Converse Chuck Taylors or Vans. If you’re not into the outrageous Vans look, then a simple pair of high or low top Chucks can add some charm to almost any outfit you slip on. They get more and more comfortable with wear, and the dye usually transforms into a more muted shade later on with some wear.
  • A Sturdy Leather Wallet:You may not be able to wear a wallet, but it’s an integral accessory to your entire style ensemble. A sturdy leather billfold style wallet becomes softer and more pliable as it ages if it’s constructed well. If you’re no longer in high school, throw away your Velcro wallet.
  • A Denim Jacket:This jacket will always be a classic. Whether you layer it in colder seasons or wear it alone as a light fall or spring jacket, this piece will improve every time you wear it. The jean jacket, or trucker jacket, as it has been known at times, will take on different wear and wash patterns, as well as molds to your body shape. The changing colors and striations only add to its unique appeal, because it takes on the characteristics you give it.
  • Goodyear-Welted Boots:A Goodyear welt is a strip of leather or rubber that traces a path on the outsole of a shoe. This boot is double stitched, making it a stronger, longer-lasting boot. They’re a touch more expensive, but they last such a long time they’re worth the small investment. These boots are meant to be roughed up and worn-in. They look a lot more appealing than if they were to remain unscratched and pristine.
  • A Leather Weekend Bag:A good weekender bag acts as a stylish accessory. You can sling one over your shoulder for a day trip, or a weekend getaway, and it will raise your style game. A weekend leather bag of any shade will slowly build characteristics such as soft lines and faded spots. These all will look great in any shade from tan to rich brown leather.
  • Horn-Rimmed Glasses:These eyeglasses may seem like a throwback to the 1950s, but they fit in with today’s style landscape. And they will add an interesting twist to your look. They go with any type of outfit, from a suit to an argyle sweater worn with a pair of jeans.
  • Argyle Patterns:Speaking of argyle, it's one of the rare patterns that still looks great being worn today. Sweaters, socks, scarves, winter caps — you name it, it comes in argyle. It is timeless and adds color and character to anything you wear. Lately, argyle has been making more appearances in men’s closets. A favorite look is jeans, a white T-shirt, and a lightweight V-neck argyle sweater over the T-shirt. This is a very stylish yet timeless look for fall.

These vintage-for-today suggestions are just that — suggestions. You can easily throw one of these pieces on as an accent piece for your outfit. They will always add an interesting “pop” to your ensemble.

Looking Stylishly Casual

Looking Stylishly Casual

Casual clothing consists of the clothes you wear on your own time. It’s all about you, and what makes you comfortable. Are you running some errands? What are you going to slip into? Certainly not your wool suit. Most likely you’re going to put on a pair of jeans, sweats, and maybe a T-shirt, or a polo shirt, right? You’re going to wear whatever makes you comfortable, and what you believe is okay to wear while you’re out in public. The problem is many men will mistake sloppy for casual. It happens. A lot. Don’t let sloppy happen to you. Your outfits should look like you planned them and perhaps put some thought into them. Your clothing reflects who you are inside. The following are some tips to help you put your best outfit forward:

  • Find a Good Tailor:Your clothes should fit. By now, you know your body and what looks good on it. You should also know a good tailor, someone who can adjust your clothing so it fits better and looks like it was custom-made just for you. Your suits should definitely be tailored to fit you. Get your blazers, casual jackets, shirts and pants taken in as well if you can afford it. Wearing tailored clothes will sharpen your look. Even your jeans should visit the tailor if they seem baggy in places. You’ll look better, and feel more confident.
  • Clothed Comfort:A man should look relaxed and confident. There’s no room for style anxiety. Look for comfortable but stylish options. Well-fitted clothing that is attractive and obviously tailored for relaxing is key. For something casual, try this lavender, pleated Guayabera shirt. It's a choice that's both stylish and comfortable — perfect for having lunch with friends or running errands.
  • Add Some Luxury Pieces:Even if you’re not a style expert, you probably know what feels cheap and what feels luxurious. Have some fun with this and spend a few extra dollars on a classic, quality piece that fits just right. Investing in a high-quality luxury piece that you can wear again and again is worth the extra cost.
  • Dress Up for a Boost of Confidence:For a special occasion, consider a casual suit. Suits don’t have to be just for work. A man always looks handsome in a jacket and tie or blazer outfit. A casual suit, tailored well, can offer everything covered above — style, comfort and luxury.

Items Every Man Should Have in His Wardrobe

We've covered timeless and casual looks to consider. Here are some essentials for every look.

  • Nice Casual Shoes:As mentioned above, it’s important to look and feel comfortable. Many styles of shoes can make you look sharp and feel comfortable. Look for boat shoes, driving shoes and booties for winter. Avoid chunky soles that are too thick. These casual slip-ons are functional and quite stylish.
  • Fitted Cardigans and Pullovers:Pair your tailored pants with easy knits for your days off. Look for argyle patterns, luxurious cashmere V-necks or crewnecks or casual fishermen’s sweaters. You can wear this lovely wool sweater with raw denim jeans for a stylish, casual look.
  • Silk Ties:If you’re working in an office, mix up your look with a collection of beautiful silk ties. Add some fun to a suit with bright colors or unexpected patterns.
  • A Leather Jacket:If you want to wear a leather jacket every once in a while, go for it — but the less elaborate, the better. A great look would be a leather jacket with a plain front. As for fit, you want a close-fitting jacket, but not one that hugs your body shape. Leather jackets that are a little bit weathered look great as well.
  • A Wool Overcoat:Get a comfortable and well-fitted coat to wear in the winter. Choosing a simple, handsome wool coat will do the trick. Make sure it's not too long — choose one that goes to mid-thigh.
  • Facial Moisturizing Lotion:Although this isn't strictly a wardrobe item, it's still something you should have to keep your look polished. Find a moisturizer with a fragrance you like or that is fragrance-free. Use one that keeps your skin feeling healthy and not dried out. If the moisturizer you’re using makes your skin feel oily or look too shiny, consider changing brands.

Looks to Avoid

We've gone through a lot of tips about what you should wear. Here are a few about what you shouldn't.

Looks to Avoid

  • Gym Sneakers:Unless you’re heading out for a run or going to the gym for a workout, there is no reason to wear athletic sneakers. Gym shoes should never become a style choice for a well-dressed man.
  • Wearing a Tie Without a Jacket:Please put on a jacket if you’re wearing a tie. Actually, it’s better if you put on a jacket even if you're skipping the tie. It just looks more polished.
  • Tank Tops and Sleeveless Shirts:No. Not even if you’re on the beach. Tanks and sleeveless shirts should never be the only thing you are wearing on your upper body. If you’re poolside or on the beach, look into some stylish T-shirts or polo shirts in soft, organic cotton. They’re very comfortable, easy to care for and come in a spectrum of stylish colors now.

Men’s Fashion Can Be Flexible

Men's Fashion Can be Flexible

These tips aren’t set in stone. Men’s fashion can be open to interpretation by everyone. These tips are meant as a guide to get you going in the right direction. If you've never been to a tailor before, don't be intimidated. Many tailors are eager to help you get the right fit because the right fit makes all the difference. That's why we offer free tailoring at Penner's.

Penner’s is a premier men’s clothing store that serves downtown San Antonio, Texas, and beyond. In 2016, we celebrated 100 years of being in this business we love. We offer suits and other fine garments, along with free tailoring. If you would like some additional information, or if you have any questions that we didn't address, please contact us.


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