1. Take a Page from Catalogs
The very first step, if you are unskilled at putting outfits together, is to subscribe to or otherwise obtain several men’s clothing catalogs. This is the best way to study what clothes go together and what clothes look silly. Sign up for LL Bean, Land’s End, Eddie Bauer, J. Crew, and any other catalog that sells clothes you like. Look at the outfits in the catalog and if you see a look you like, rip that page out. If you don’t want to purchase the clothing from that store, simply take the page to a store you do shop at and try to find something similar. It will help the store associates find you something you like if you have a picture of what you’re after.
2. Shop Wisely
If you find something you like and it fits perfectly, buy a couple, perhaps in different colors (online shopping sites for deals and coupons can come in handy here to save money). If you find that you like the clothes in a particular store or catalog, sign up for their email list, since that is where most sales get announced. Solid-colored clothes are generally a safer bet than prints and will go further in your wardrobe; prints on pants are pretty much never a good idea and nearly impossible to match. Don’t take the tags off as soon as you get home and keep the receipt until you are sure you want the item. Finally, even though great clothes can be found from time to time on clearance racks, remember that stuff ends up on their for a reason.
3. Buy Clothes That Fit
You can probably figure out when clothes are too tight. But it takes a little more finesse to figure out if the clothes are too big. The crucial thing to remember is that you will look as big as your clothes. If your clothes are two sizes too big, you’ll actually appear to be two sizes fatter. No one wants that. Everyone, even big guys, look a hundred times better with properly fitted plus-size clothing. Shirts should skim the body without being any baggier in one location than another, and should fit properly around the shoulders most of all. And unless you are built and have no choice, short sleeves should be loose enough around your arms that you can get a finger or two under the cuff. Long sleeves should not cover your hands. Pants should not bunch up around the crotch, and should not touch the soles of your shoes when you are standing up. No one looks good in pleated pants, some people just look “less bad.” Buy flat-front pants. And please, for the love of Pete, your underwear should not be showing. Pants that are too big look good on no one and look even worse when they inevitably fall down.
4. Remember to Hem
So many men do not get their pants hemmed properly, if at all, and it is really such a simple step. It is inexpensive to have done, but it makes your pants look a hundred times better and keeps them from getting frayed at the bottom, which looks terrible. If you find pants that fit but are just a mite too long, that is always preferable to pants that are a mite too short, since you can just get that extra mite hemmed off. Find a local tailor – check Yelp or Angie’s List for recommended local services and professionals, or ask the ladies in your office – and try on your pants for the tailor. He or she will measure and pin them, and you can pick up your perfect-length pants in a couple days. This usually is less than $10 for an uncomplicated job, and will save you money in the long run. Tailors are not just for hemming pants, though – sleeves that are too long, especially on jackets, should also be shortened, and they can take in the sides of a shirt if it is too baggy.
5. Choose Colors You Like
Don’t stress about whether or not a color looks good on you. Most colors look fine on anyone as long as the color itself is not sickly. (Do not buy puce or chartreuse – or anything else the color of throw-up.) Don’t buy pink or purple if you will feel self-conscious – they’re fine color-wise, but an uncomfortable, ill-at-ease man is always out of fashion. For ease of matching, if you are truly terrible at it, just pick a couple of colors and buy all your items in those colors. I had a friend in high school who was colorblind and so every shirt he owned was green, blue, or white and he only owned khakis and jeans. It worked great!
6. Never Wear All Black
It is not slimming. It merely makes you look as if you have no other clothes. If you are wearing a black shirt, you should not be wearing black pants. If you think you look better this way, you are mistaken. In fact, do not wear any matching top and bottom at any time. This makes you look like you bought your wardrobe from Gymboree. The only exception is if you are wearing a suit or a tuxedo.
7. Don’t Forget the Belts and Shoes
Do not wear a brown belt with black shoes, or vice versa. Men don’t get to wear lots of accessories, so make sure the ones you do wear look good. (And yes, a belt is an accessory, even if it has a function.) Every man should own a nice flat black leather belt (a continuous, single piece of leather, with no braiding or stamps or any other decoration) and a pair of nice black leather shoes. And learn to polish them! Wearing these with dark-wash jeans and a button-down is a great date look and will make you look like you know what you’re doing!
8. No Short Shorts
Please do not wear jean shorts to do anything more formal than changing your oil or unclogging a toilet. You should wear khaki shorts or cargo shorts for casual days, and you are prohibited from wearing shorts to work or anywhere else remotely non-casual, unless you work on a boat or in an ice cream shop. Your shorts should hit somewhere around the knee – if the hems are in your thigh area, they look silly, and you can probably see up the legs when you sit. No one wants that. Shorts can be baggy in the legs, but not the waist or butt. If you are appropriately jaunty, you may wear a polo shirt with your khaki shorts on summer weekends.