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27 men's fashion do's, don'ts and maybe's

Written by
Nick Kotecki

Fashion options for men are abysmally uniform when compared to the variety of outfits available for the opposite sex. Many guys simply get by: button down, button up, some pants, a belt, some shoes, shorts on a warm day. 

There are ways for the average dude to make do, though. Most of it boils down to complementing old standards with a personal touch that doesn't overwhelm.


Yes, please.

Match your belt with your shoes

Men's fashion 101 here: just do it. Your shoes and belt don't have to be exactly the same color, but keep it close.

Shave your neck

Your beard might be majestic, and a bit of a neck beard is okay, just don’t let it connect to your chest.

Wear colors

Try some pastels. Try a button-up that isn't blue, gray or black. The field is a bland one, so finding something that isn't tasteless or over-the-top isn't as hard as it may seem.

Denim shirt

These are a nice compromise because they're the epitome of business casual and extremely comfortable. Also, they look damn good on just about anyone.

Black jeans

Like a denim shirt, these have a classiness of the casual sort. Black jeans also double as perfect concert and nightlife wear. For those of us who can't seem to keep food off our clothes, these slacks are nearly stain-proof.

Nice boots

Even when snow is on the ground, always have an alternate pair of boots that aren’t your winter shit kickers.

Own at least one tailored suit

One is good enough. You can tell when a suit is too big if the shoulders bunch up when you raise your arms or if the shoulders appear bunchy when your arms are at rest. Spend money on tailoring when you buy a suit, it really makes all the difference.

Summer shoes

That being said, going into summer is a great time to buy a cheap pair of Vans, boat shoes or flats.

Fun socks

Summer footwear brings the chance to show off a nice pair of socks that go beyond the standards. Skip white socks altogether.

Crew neck T-shirt or a slight v-neck

Don't go for the plunging neckline. The classic crew neck shirt will always be in fashion, and a v-neck that dives 1 to 2 inches below the neckline will do. No more, no less.

Above all, wear clothes that fit

Buy fitted clothes when possible. Most guys aren't built for skinny jeans and bootcut pants are always on sale for a reason, they just look gross. Bottom line: You don't want to be swimming in fabric or have your stomach show when you lift your arms to yawn.


No. Never. Not ever.

Sandals with socks

If it’s too cold to wear sandals properly, don’t at all. One of our (female) staffers insisted men not wear sandals at all, especially flip-flops.

Sandals when it rains

Ladies are more frequent offenders here, but men are still guilty. Walking in sandals in Chicago is already kind of gross, not to mention through the Loop and CTA when it rains.

Shorts when it’s 50 degrees

You get a free pass on the first mildly warm day of spring. Within a week, your body will adjust, and it’s time to hold off until the 70s arrive.

Baggy shorts below the knee, or tight shorts with lots of thigh

Go with a pair that cuts off just above the knee or a few inches higher. The loose factor is up to you, but err more on the side of a regular, streamlined fit.

Drug rugs

Just wear a regular hoodie. Baja ponchos basically advertise that you’re the wrong kind of stoner. If you must, keep this oversized hacky sack to your lazy Sunday or sleeping clothes.

Sneakers with dress clothes

Dress shoes are for looking good on the street and in the office. The amount you invest in a good pair of comfortable dress shoes will be worth the endless stream of crappy dress shoes and sneakers you are constantly replacing.

Blue button downs every day 

This wardrobe workhorse has been a staple for years and years, and for good reason. It’s stylish and easily available at almost every kind of clothes store. Just don’t make it an everyday thing.

Shave your unibrow

They’re called tweezers, dude.

Wear a Cubs hat on a first date

Or any hat, really. That means you too, balding dudes. Own your dome and whatever hair fate has graced you.

Wear a full suit for your job interview

If you're not an executive, or in high-stakes business or banking, it will be very difficult to take you seriously. There’s nothing a nice dress shirt or sweater can’t do. Wearing a suit to an interview just shows off your inner Midwest bumpkin.

Half tucked-in shirt

Be sure to monitor the status of your tucked-in shirt throughout the day. That little frumpy shirt bulge often seen above many a belt-line is not attractive.

Wearing boots with cuffed pants

Cuffed pants and chinos are in, and men have a bigger selection of boots than ever. Unfortunately, the two don’t mix.

Cargo pants or shorts or anything with cargo pockets

What are you going to put in those pockets, really?


It all depends on how you hold yourself.

Pocket square

This might be best saved for a wedding or for those who would like to add personal flair to an important meeting. Do not match your pocket square with your tie. Instead, choose a complementary color. Red tie? Go with a nice blue square. Black tie? White square. Blue tie? Green or red. Treat bow ties the same as the regular variety. Don’t be afraid to ask a knowledgeable clerk for help.


A nice pair will go a long way with dress attire. Just be sure to match the metal clasps with the metal of your belt and cufflinks, if you're rolling fancy.

Salmon-colored pants

Not everyone can pull off these hideous wonders that return every spring, but some guys really can (full disclosure: the author definitely cannot pull them off).

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