Dress Better By Avoiding These 10 Rookie Errors

Rookie style mistakes

When it comes to improving your style, most advice requires you to buy something new or spend money on clothing alterations. You could call this additive advice.

Buy those. Wear this. Spend more money of that.

Even if it’s great advice, sometimes you just don’t have the time or money to implement it.

But what if there were ways to improve your style by avoiding certain mistakes (i.e. subtracting certain garments or behaviors)? Rather than buying a new piece of clothing, what if you simply avoided certain combinations?

Well, I have good news for you. There are ways to improve your style with minimal investment, and they’re very easy to follow right now.

Here are 10 style mistakes that every man should try to avoid.

#1: Wearing athletic socks

The only time you should wear athletic socks is with – you guessed it – athletic shoes. You know, when you’re doing athletic things like playing sports or working out.

It doesn’t matter what kind of athletic socks you prefer (long, short, etc.) – they don’t go well with any shoes that aren’t meant specifically for sports or fitness.

White socks with sneakers

Not cool, man. Not cool at all.

If you’re wearing shorts, you should probably avoid visible socks altogether. This doesn’t mean you have to go completely sockless with your loafers and boat shoes. Try wearing no-show loafer socks for extra support and comfort.

Falk invisible step socks

MUCH better!

But please, my friend, save the athletic socks for the gym.

#2: Wearing backpacks with dress clothes

GQ tries to tell us that it’s okay to carry a backpack to work, as long as it’s designed by some Italian whose name I can’t pronounce and costs more than my rent.

Wearing back pack with suit

Don’t be this guy!

But you already know that GQ lies to us. The truth is, it doesn’t matter if a backpack costs $25 or $2,500 – it’s still not appropriate for a business casual or formal environment.

Unless you’re a student, you should avoid wearing a backpack (unless you’re hiking, that is). If you need to carry a laptop, use a laptop bag (like a messenger bag).

Otherwise, find a small men’s bag that fits everything you need to carry on a daily basis.

Some people love backpacks. You might be asking yourself right now, “But what if it’s a stylish backpack?” Well, if you really want to carry one, that’s your choice.

But it’s best left for casual looks. If you’re dressing in business casual or formal (suit and tie), you should definitely leave the backpack at home.

#3: Wearing casual belts with dress pants

Casual belt vs dress belt

Bottom = less casual

Every man has a thick leather belt. It’s probably old, supple and marked up.

It’s probably about 1.5″ thick and looks great with jeans. And it probably looks really bad with dressier outfits.

Dress pants (like trousers or suit pants) go best with thinner, more formal belts. Short men should opt for belts that are no more than one inch thick.

You should have a few belts to choose from, since it’s best if your belt matches your shoes. Plus, wearing the same belt everyday will lead to rapid aging (of the belt, not you).

#4: Wearing an “outdoor” coat over a suit

Imagine you’re walking into a coffee shop on a cold winter day, and you see a middle-aged man in an expensive suit. His shoes have clearly been polished recently, and his hair is parted neatly.

Parka over suit

CEO or mountaineer??

Everything is looking good, but what does he top this dapper outfit off with? A big, puffy down parka!

This ruins the whole getup because parkas (or any casual, cold weather jackets) are inherently rugged, technical and sporty. Suits, on the other hand, are refined, sleek and elegant.

It a confusing mashup. Are you on your way to the boardroom or a woodland winter adventure?

There’s a time and place for casual outerwear, and it’s not when you’re wearing a suit and tie. Parkas (and the like) are inherently rugged, sporty and technical.If you’re wondering what kind of outerwear you should be wearing, read this post:

Outerwear for Short Men <–

Don’t get me wrong: I’m all about function over form. In certain climates, you need to wear the warmest, most insulated coat you can get your hands on.

And that’s okay. You can pull this off when necessary. But know that a wool topcoat will always look better over a suit than a bulky winter parka.

#5: Wearing dress shirts untucked

There are button up shirts that are meant to be worn untucked (often called “button downs”), and there are button up shirts that are meant to be tucked in (often called dress shirts).

Dress shirts are cut longer than casual button ups so you can tuck them in. They also have a curved hem line that creates a “tail” in the front and back of the shirt:

Button up shirt hem shape

Straight Hem (left) vs. Curved Hem (right)

Here’s the thing: you can’t just convert your dress shirts to casual shirts by untucking them. It looks horrible, especially on shorter men (because dress shirts are always way too long).

Wearing a dress shirt untucked

Instead, keep them tucked in, or make sure to only wear button up shirts that were meant to be worn untucked. These casual button ups will be hemmed shorter, and the “tails” won’t be so pronounced.

In general, casual shirts will also have more casual details – button down collars, chest pockets, contrast plackets, contrast button stitching, etc.

#6: Wearing dark socks with light pants (and vice versa)

White socks with dress pants

Just say ‘no’ to this look. (Source)

This one is easy. Avoid dark socks with light pants, and light socks with dark pants.

For example, don’t wear black socks with khaki chinos. Don’t wear white socks with charcoal slacks.

When in doubt, match your socks to your pants. It’s okay if they’re slightly darker, but try not to go too much lighter (unless you want to make a statement).

Oh, and crazy/bold/loud/colorful socks?

Overrated.

#7: Wearing dress shoes with jeans

Did you know that jeans were originally created as work pants for coal miners? That’s why they’re so tough and rugged. These days, jeans can be dressed up by throwing on a blazer and some nice shoes.

But light wash jeans? They’ll never look good with dressy shoes.

Square toe shoes with jeans

Left = not great; Right = really bad

In fact, almost all denim will look weird with black dress shoes (except for fitted and black or very dark blue. If you’re going to wear dressy lace ups (like Oxfords), opt for brown instead of black.

Better yet, just wear boots. From chukkas to work boots, you really can’t go wrong. It’s much easier to pull off the smart casual look by wearing jeans with dark brown ankle boots then it is to try and match jeans with wingtips.

#8: Wearing boat shoes with dress pants

Boat shoes are really meant to be worn with casual outfits, like shorts or cuffed chinos. Even though they look like loafers, they’re not meant to be worn with dressier pants, like wool trousers.

Boat shoes with trousers

Close…but not quite right. (Source)

This is subtle, but if you look closely, you’ll see it everywhere, especially during the warmer months.

Penny loafers (like these, these or these) make great alternatives to boat shoes.

#9: Wearing v-neck sweaters with nothing underneath

This rule is breakable, but in general, v-neck wool sweaters are layering pieces. They look best when layered over a button up shirt.

V-neck sweater worn alone

Something is missing…

This is especially true for short men, as the ‘V’ will often be extra deep, showing off way too much chest (or worse, chest hair).

If you don’t want to layer, or maybe it’s too warm, swap the v-neck for a crew neck sweater. It’s a much better shape for wearing alone.

#10: Wearing casual watches with dressy outfits

This is another classic mismatch that happens way too often. In terms of formality, watches fall into a pretty clear ranking:

Leather strap dress watches –> Metal “diver” watches –> Rubber or canvas strap casual watches –> Digital watches

Matching Your Watch Infographic

Click for full size image

Of course, their are many types of watches, and some fall into more than one category. There are all sorts of “in betweens” and fusions.

If it’s all a bit confusing, this infographic from RMRS is a good quick reference guide for pairing watches to different types of outfits.

Just remember this: watches are like shoes. It’s okay to wear a dressier watch with a less formal outfit. But you shouldn’t wear a casual watch with a formal outfit (for example, a field watch with a tuxedo).

Conclusion

Everyone, myself included, has been guilty of one or more of these mistakes. It’s a lot to remember, and some of these things are a bit counterintuitive.

If you can avoid these rookie errors, your style will be light-years ahead of most other men.

And remember, almost every rules can be bent and broken, but you have to know the rules before breaking them.

Do you agree with this list? Speak your mind in the comments section!

Comments

  1. What you thoughts on wearing a smart watch with dressy outfits? Like Apple Watch or Microsoft Band 2?

    • With smart casual or even business casual, I think they’re okay. With formal outfits (like formal business, black tie or evening wear), a dress watch is a much better choice.

  2. Great article!

    Where can I find that black belt in the photo?

    • It’s actually pretty old… not sure where I got it. It’s of the hole-less variety, so it’s got the ratchet/slide type buckle, rather than traditional holes.

  3. Hey Brock,
    I almost agree with you. But in my opinion, we can wear backpack with shirt without suit.
    The backpack should be from leather material. If you wear suit, off course you can’t just use backpack

    Regards
    The Fashion For Men

  4. Let me say that it was one of your posts Brock, that led to me buying my first pair of brown shoes ever. But I am not sold on brown being better than black with jeans. I think your point is don’t wear dress shoes with casual looking jeans at all. Agreed. But work boots, desert boots or other casual shoes, I might still wear black most of the time. For instance, black leather jacket, light jeans, black boots ( barefoot boots, that is!). With blue denim I almost always choose black footwear.

    Andhika, I agree but not from a fashion standpoint. Backpacks are the best for your health as they don’t unbalance you structurally. Leather is a good choice to minimize the style-damage. If you can’t or won’t use a backpack, try not to walk long distances with your shoulder bag or briefcase. After a while it will catch up to you.

  5. Emmanuel M'M says:

    I will keep the backpack and formal wear. The weight of my machine is way too much for a messenger bag

  6. Hello! I’m a Brazilian man who likes to read your page although nos as often as I would like. I’d like to compliment you on the good tips about style errors. Sorry for any English mistake.

  7. that photo of the light blue jeans with the dress shoes is awful

  8. Antonymous says:

    I always wore similar ankle socks with shorts and shoes, just not white as here :), I like the look if worn with knowledge.

  9. Don Renollet says:

    Good guidance again !!

  10. Matching a watch with an outfit can be as simple as one, two, three. But, it can also be nerve-wracking if you lack the basic knowledge to do it. Very useful & interesting tips. Thank you a lot!

  11. Thanks for the amazing tips Brock!

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