As fashion has evolved through the years, it has become particularly difficult to “dress for success.” The kind of success we are looking for varies constantly, with each day bringing a new set of needs and expectations.

This muddying of the waters has made it especially treacherous in the realm of men’s fashion. A V-neck shirt and jeans to the first date? What about the second? And what are you going to wear to that meeting with your advisor, maybe even the dean of your college?

And even when we arrive at the proper level of dress, the challenge only becomes harder: Trends and styles are now in play. The suit you bought a few years ago might have an outdated fit, or your shirt might be too boring compared to today’s trends.

No matter what the case may be, this guide is here to help you make sense of style this winter.

When it comes to casual dressing, it’s not entirely possible to be serving your best look day after day. Simplicity is the name of the game. In this game, layering is your most reliable play.

Take your best jacket, for instance. It might be a military surplus, a Letterman jacket or even a pea coat. Now, while this jacket might be stylish, it’s uninspired on its own. Try mixing and matching combinations of button ups, t-shirts, flannels or even graphic tees for a splash of color.

With this layering comes the opportunity for creativity. Throw in a scarf, a sweater, an undershirt. Men’s scarves are underrated and underutilized in our wardrobes. It’s cold outside, and who would say no to the chance to accessorize?

However, be sure to coordinate your color palettes when throwing all these layers together. Your eye will be drawn to complementary color combinations: Think earth tones, reds and grays, blues and yellows, even a monochromatic look. Simply be mindful that you don’t get carried away.

You’ve now expanded the number of outfits your wardrobe can produce. With simple colors and common-sense combinations, casual wear brings more to the table.

Going toward more formal types of style does not always mean going straight for a suit. Sport coats have long been trusted options for a middle level of dress. This space between smart casual and formal wear is where you have the best opportunity to show off your individual style.

Consider going with bold colors, even in the coat itself. Ties are optional, but creativity is encouraged. Try to stay away from ties with too much of a sheen to them; this may appear incongruous with your more casual outfits.

This might also be the time to work in a sort-of trademark for yourself. Do you like suspenders? Bow ties? Unique shoes? Mix one of these fun options into your mid-range style to set yourself apart from the crowd. Being a trendy dresser should not cause you to lose your individuality.

For some who already have the essential suits – black, navy, gray, perhaps even a lighter summer color – it can be hard to find a way to expand your lineup. I suggest looking at more casual suit options. These suits can be patterned or even made out of wool alternatives.

Pinstripe, windowpane or tweed suits can freshen up the occasionally monotonous landscape of men’s formal wear. Though some are not suitable for the most formal of occasions, they can play a valuable role as an everyday sort of suit.

Moving into the fanciest level of dress, below black tie at least, it is important to remember that there is no such thing as looking too good. Pull out all the stops for any occasion you get the opportunity to show off the best of your wardrobe.

Tie pins, cufflinks, pocket watches, rings – it’s all fair game here. Dress for the satisfaction of seeing yourself when you pass your reflection, and the rest will take care of itself.

The winter weather allows for the use of overcoats in outfits. While they are primarily for warmth and rain, don’t underestimate their ability to add to the ensemble. Black and khaki remain classic options that never go out of style.

In every area of your wardrobe, remember this: Your style is yours. No matter what “fast fashion” companies or magazines would tell you, things are not “in” one day and “out” the other.

A good sense of style is timeless, and it does not need constant updating. That’s why vintage styles always seem to be making a comeback, why Cary Grant still looks good in films that came out 60 years ago.

Being fashionable does not have to be a problem of personal taste, wealth or self image. Simply put thought into what you wear, and then wear whatever it is with pride. You’ll notice the difference.

Special thanks to Jonathan Holle, Max Bergstrom, and Karl Pruitt, II.