7 Ways to Pair a Classic T for a Different Look

December 8, 2022

From walking the streets with a date in hand to dominating the boardroom after a new merger, how you look plays a vital role in how people treat you. While some prefer the traditional suit and tie, others enjoy a more versatile option that can complement practically any look you want. That is where the classic Men’s premium t-shirt comes into play.

The classic tee is a wardrobe staple for every guy. Pairing a classic tee with different pieces and accessories can help you create looks for practically any occasion. It’s all about finding quality material that can handle multiple piles of washing without losing the fit and structure of the fabric. Choosing a well-made Pima cotton t-shirt is the best way to build a wardrobe where you can quickly grab a few items from your shelves and get out the door to whatever appointment or event is next.

You can wear your favorite tee in a hundred different ways, but it's always nice to shake things up. Having a set of quality tees which are tailored and designed with versatility in mind, in various colors, allows you to pair any outfit for any occasion at any time of year.

A Note on Colors…

Without going into a complete color-pairing guide, it goes without saying that you should be purposeful in how you match the color of your T with whatever you are wearing. As a general rule-of-thumb, whenever you choose a T-shirt in the core color group (black, white, navy, gray) that is your opportunity to go with something a bit more distinct elsewhere. The same applies vice-versa – if you are going with a more bold t-shirt color option such as dark red or light blue, then you will want to pair it with something a bit more neutral.

With that out the way, here are our tips for boosting your classic tee look by combining it with some men’s wardrobe staples:

Tip #1 - Pairing with Classic Jeans

Jeans are a classic and versatile piece of clothing. They can be worn with a tee to create a casual look or paired with a blazer for a dressier look.

Classic dark-toned jeans that fit well are foundational to any man’s wardrobe. You can stick to the jeans and t-shirt look when it's warmer out or toss on a moto jacket for an edgier look. Every man should have a quality pair of jeans and a few tees to mix together.

Tip #2 - Combining with Casual Shorts

One of the best ways to wear a classic tee is with shorts. Just make sure the pattern of the shorts doesn't compete with the shirt too much and that it's not so busy that it distracts from your outfit (we're looking at you, paisley).

Since shorts come in so many varied colors and fabric, this is a great opportunity to re-emphasize the importance of being purposeful in how you pair non-neutral colors. Stick to single-tone colors that you can mix and match. This is perfect for traveling on vacation to warmer climates (more travel tips here). Our recommendation for a week-long tropical holiday: two neutral color shorts (gray, khaki, navy, etc.) and one colorful option (yellow-, blue-, red-tones, etc.). Pack a mix of both core-color Ts and some more colorful options, and before you know it, you have a distinctive look for each day!

White T-shirt worn with light blue shorts

Tip #3 - Creating a Professional Look with a Blazer

Despite a recent trend towards less-formal attire, wearing a plain T-shirt to a work lunch or a nice restaurant is still probably not going to send the message you would hope for. Luckily, the simple addition of a blazer or sports coat, however, can magically elevate your look in no time! This gives your outfit more structure and makes it look more professional. The blazer also works well with casual jeans and sneakers, if you want to dress down a bit.

Again, simple colors that are more classic in tone elevate the overall look by creating a professional appearance through the scope of minimalism (think Keanu Reeves more than Kanye West).

Tip #4 - Staying Edgy with a Jacket

A jacket is a great way to add a little edge to your outfit. A jacket can be worn with a classic tee to create a more formal look or paired with casual shorts for a more relaxed look. This will keep you from getting overwhelmed by all the available options and help you find something that works well within your personal style.

You also may want to spend a little time on what jacket style to select, as that will become the centerpiece of your look. Our suggestions are Bomber, Leather, Denim, Harrington, Field, or Moto.

Tip #5 - Layering Under a V-Neck Sweater

A V-neck sweater is a great layering piece and can be worn over a tee or under a jacket for added warmth. It's a great way to add color to an outfit, but it also looks great in neutral colors. One thing to note: this is one of the few times where we not only condone but highly recommend tucking in your T so that it does not show below the bottom of the sweater.

This look will never go out of style, so if you're looking for something classic that will last forever, this is the way to go.

Tip #6 - Adding Contrasting Colors with a Cardigan or Zip-Up Sweater

A cardigan or zip-up sweater is a great way to add contrast to an outfit. These versatile pieces can be worn over a tee or button-down shirt with jeans or chinos.

Cardigans come in many different styles, so mix them up with different patterns and colors. Try not to go all the way into the “ugly Christmas sweater” zone with a cardigan. You’re looking for a more George Clooney/Ryan Gosling look than Weird Al Yankovic.

Examples of T-shirt worn with zip-up sweater or cardigan

Tip #7 – Staying casual in a Zip-Up Hoodie

One of the best ways to wear a classic tee is in combination with one of your favorite hoodies. This can be paired with jeans, shorts, or even khakis.

It's important to note that this look works well in cooler weather and doesn't require heavy boots or sneakers—a pair of classic white high-tops will do just fine. As in most cases, when layering an item over your T, you want the length of the T to not fall below the bottom of the hoodie itself.

It's All About the Classic Men's Style

The classic tee is one of the most versatile pieces in a man's wardrobe. You can wear it to work and pair it with dress slacks and oxfords. You can wear it with jeans on the weekend or even throw it under a blazer for an evening out. The possibilities are endless.

The best way to ensure you get as many options as possible is to select materials from the best fabrics. At IF… THEN WELL, we focus on premium men’s Pima cotton t-shirt bundles sure to elevate your wardrobe choices. Our Ts are designed for a timeless look, made from quality that will hold up through multiple washes and ultimately will hopefully provide you with one less decision to make each day… what to wear.

We hope these tips have given you some ideas for how to wear your classic tee in new and exciting ways. The truth is that there are plenty of other options out there, but these seven are our favorites for staying sharp and looking great all at the same time.

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