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How to Dress Well: 9 Rules to Help You Go From Frumpy to Sharp

July 23, 2020 5 min read

How to Dress Well: 9 Rules to Help You Go From Frumpy to Sharp

2020 has been the year of the mullet outfit: professional on top, comfort on the bottom. Put on a shirt, tie, and blazer on top but keep the pajamas or shorts on the bottom, right? No one knows this better than Will Reeve, an ABC News reporter who showed off a little bare leg during his segment on GMA when he panned his camera a little wide while reporting from home.

Now that offices are starting to reopen and people are venturing back out, it's time to stop dressing like a college student. If you want to learn how to dress well, you're in the right place.

Read on for 9 style tips for men.

1. A Tailor is Your Friend

It's hard to buy clothes off the rack and have them fit perfectly. This is where a tailor comes in. A tailor isn't just for suits. You can have pretty much everything tailored, including jeans, khakis, shirts, and blazers.

Find a good tailor and visit them regularly. They can tailor your new clothes as well as those things you have in your closet that you love, but just don't fit quite right. It's much cheaper to have something tailored than to buy new clothes when your old ones don't fit.

2. Know When to Splurge, and Know When to Save

Being a well-dressed man doesn't mean you need to be dressed in designer clothing from head to toe. Instead, know what to splurge on and where to save your money. Splurging on things you'll wear often and those that are timeless, such as a well-tailored suit, a nice watch, good shoes, and well-fitting jeans is smart.

You can save on other things, such as trendy items that won't be in style forever. There's also no need to splurge on things like t-shirts, shorts (especially if you only get to wear them a few months a year), and loungewear.

3. Wear the Right Shoes

We've all seen the men wearing a polo shirt, dad jeans, and cringe-worthy white dad sneakers. You know which ones we are talking about. Bad jeans aside, let's talk about the proper shoes.

Certain outfits go with certain shoes. Boat shoes, for example, are not appropriate for the office (unless, of course, you work on a boat). Ditch the man sandals (man-dals, if you will).

Sneakers you would wear to work out should never be worn with a nice outfit. If you want comfortable sneakers, opt for a pair of plain white leather ones or a sleek pair of trendy trainers.

Invest in a few pairs of high-quality shoes, such as a good pair of sneakers for working out, modern or trendy athletic shoes, leather oxfords, and leather boots.

4. Know How to Accessorize

Learn how to accessorize with items that will put the finishing touch on your outfit. A nice watch, cufflinks, a pocket square, sunglasses, a lapel pin, and a hat are all accessories that can complete your look.

If you're wearing a dark suit and white shirt, a pop of color from your tie or pocket square can elevate your look. Cufflinks will instantly upgrade a dress shirt and you can even add a scarf to your look in the winter.

5. Embrace Layers

When done right, layers can make even the most boring dresser look stylish. Some layer combos that work for most men include a button-down shirt and a sweater, a jacket, button-down, and sweater, and a vest and a henley.

If you're in doubt, check out the outfits on the store mannequins or get on the internet and look up some outfit combinations to take the guesswork out of it.

6. Wear the Right Outfit for the Occassion

Make sure your outfit fits the dress code for the occasion. An evening wedding, for example, might call for a tuxedo (if it's black tie) or a dark suit and tie. An afternoon or morning wedding calls for a lighter suit in many cases.

What you wear to a job interview might be more formal than what you would wear on a daily basis at work. It's important to read the room. If everyone else at work wears a shirt and tie, you probably shouldn't show up in khakis and a polo shirt.

7. Well-Dressed Means Well-Groomed

You could be the best-dressed man in the room, but if you need a haircut, a shave, and your nails look like you've been outside digging in the dirt, no one will notice your clothes.

Get regular haircuts, style your hair, keep your beard crisp or clean-shaven, and make sure your nails are clean and filed. You don't need to spend tons of time on grooming either. Just make sure you keep up with it so you don't ruin all of your hard work on looking good with scruffy hair.

8. Dress for Your Body Type

Life would be easy if you could walk into any store, pick out clothing in your size, and have it fit perfectly. Unfortunately, that's not the case. Not all brands fit the same, not all styles work on everybody, and some colors or prints just don't work on some men.

Figure out what works for you and stick to that. Find a few stores or brands that fit you well and buy the majority of your clothes from them.

This is also where your trusted tailor comes in. They can work wonders on ill-fitting clothing.

9. Take Care of Your Clothes

While it's tempting to throw everything in the washer and then in the dryer, actually take the time to read the labels on your clothing. If it's dry clean only, don't try to wash it at home. If the label says hang to dry, do that!

Don't wash everything in hot water either. Read your labels to keep your clothes looking their best. If you're missing a button, or the hem on your pants has come un-sewed, hit up your tailor. Small things like that can ruin your look.

How to Dress Well for Every Occasion

Now that you know how to dress well, you can make sure every outfit you wear fits well and is fashionable. Dressing well doesn't have to be expensive or overwhelming; find some style inspiration and learn what works for your body.

Art of the Gentleman is your go-to for all of your accessories. Whether you need a tie, bowtie, lapel pin, pocket square, cufflinks, socks, or suspenders, we've got them.

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