A Preppy Man's Guide to Matching Clothes

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How to match clothes

You know how to put on a suit and you know how to throw on jeans and a t-shirt — but what about something a little more exciting?

Is that your pain point? We're here to help. You're about to go from "unnoticeable fashion sense" to "compliments galore."

Learn how to match clothes below.

Step 1: Have the Basics

Part of matching the right outfits is starting with classic pieces. That means you may have to go shopping. We recommend going to a place like Kohls or Target, which have different brands for every budget. 

Those different brands may fit you differently as well, so it's good to have options.

Here's a quick guide to the basics you need in your closet.

Medium Wash Jeans

Too many men wear faded out 90's color blue jeans because it's all they've ever known. Those are fine for casual use, but a darker wash dresses up your look a little bit. Aim for a straight or "skinny straight" leg cut.

Khakis or Chinos

Khaki colored slacks are another basic. You should have at least two pairs — one nice dress pair and one that's a little more casual.

These should fit your leg but have enough room so the fabric moves around a little bit when you pull on it.

If you're a unique height, make sure you get "tall size" pants or, if you're shorter, have them hemmed properly.

A good fit is the first step to a good look.

Navy and Khaki Shorts

While jean shorts might be trending right now, they're a fad and they'll die out again. Stay away from them unless you want to look like the funny guy in a 90's college comedy.

You want to find shorts that go to about two to three inches above your knee. Solid colors will work for these when you're wearing patterned shirts (more on this later).

Shorts with a Minor Pattern

Do you know what seersucker is? It's a cotton fabric that breathes well and has very close white and (traditionally) blue stripes. Seersucker fabric is classically preppy, and you'll find a lot of it on golf courses.

If you don't like seersucker, you can look for a short with small embroidery detail. These are usually solid color shorts that have some symbol in a bright color every couple of inches.

Flamingos, sailboats, pineapples, anchors — you can find just about anything. Pick one you like and stick to a darker color background at first.

As you get more comfortable in your fashion sense, you can move on to wilder colors.

Shirts You Need

Next, let's talk about what you'll wear with your basic pants now.

Casual Polos

You should have a few collared cotton shirts in your wardrobe for nice-casual occasions. These are the kind with short sleeves and buttons only a few inches down from the neck.

Get a white, black, and one bright colored option to start.

Button Downs

You should have the same mix (white, black, and bright) of long sleeve classic button-up shirts.

You'll wear these on more formal occasions. You can pair one with jeans or khakis.

Short Sleeve Button Downs

Here's where things get a little more fun. You want to get a white button down short sleeve shirt in a light material. Cotten or linen (and blends) are great.

Get a white and another neutral color. Then get at least one (if not two) shirts with a pattern that stands out to you. For the fashion beginner, it may look a lot like the patterned shorts you bought.

Plaids are always a good way to start playing with patterns.

A Few Nice, White T-Shirts

If you watch any Queer Eye (and if you don't you should - free fashion advice on Netflix), you know that buttoning up a shirt isn't mandatory.

You can wear a button up open or half buttoned over a white t.

Putting Basics Together

Now that you have your basics, let's talk about your combinations. First, you need to know what neutral colors are.

Neutrals are blacks, browns, whites, grays, and khakis. You can wear brown and khaki together, brown and white, and dark brown and black.

White and black go with everything — these are your most versatile pieces.

Your Foolproof Combinations

Here's where all those basics come in. There are three main combinations of colors/clothes/patterns that you can create infinite outfits from.

The Top-Pop

If you're feeling traditional, pair a neutral bottom with a colorful top. That can be a pattern or just a color. Khaki shorts with an emerald green polo? Perfect.

The color on top with a neutral bottom — that's combination #1. 

The Bottom Heavy Color Option

Let's say you want to show off those new shorts you just got that have crabs embroidered on them. You're wearing a pattern on the bottom, so you wear something neutral on top.

Colorful bottoms and a neutral top — that's combination #2. 

The Fashion Expert

Once you've spent some time playing with neutrals, you can combine the two outfit types. Let's stick with the crab shorts. Let's say the shorts are khaki with red crabs.

Pick a red solid color shirt to go on top, and you have a coordinating, matching outfit.

Try to buy shirts/shorts that have similar color combinations so that you can use your pieces in different outfits.

How to Match Clothes: Class Is Dismissed

You thought fashion was complicated? It turns out that there are only three main combinations to know. When you're getting dressed in the morning, decide what type of outfit you want to wear and add the appropriate pieces.

Voila — you now know how to match clothes.

Feeling inspired and need some new clothes to practice your skills with? Shop here.

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