How to #DressYou

Over the past year, I’ve had the opportunity to further focus on my fashion-tech app after a long period of focusing on my career, and oh my, how the world has changed! Post-pandemic in particular, what we regard as fashion-conscious or proper etiquette in certain situations or places have all changed radically, if they have not been eliminated completely, and that's okay!?

I started to think that this may be more than just a shift in workplace policy, but an aggregate change in social perception and behavior. I like to think these days that we place much greater value on the ability to express ourselves in our own way, regardless of what position we may hold or what we may have been expected to wear in the office years ago. We have a yearning now; a yearning to be comfortable being authentically us. That could be feeling great in a well-fitting suit, or just doing you in a casual sweatshirt and sweatpants combo. Whatever outfit you may decide to wear, the most important thing is not that it may invite others to judge you unfairly, but that it makes you feel like you.

Folks put more or less personal value on how their outfit expresses their personality, but to many, their outfit is their second skin; a way to be able to focus on being themselves. That’s a hard thing to do if you've never felt comfortable in your own skin. Back in K12, I was not the most savory looking kiddo. I was heavy, short, and was the last person to pay attention to coordination or comfort (I’m sure this sounds familiar to a lot of you). But, I remember spending my first paycheck as a new intern back in college on a suit, and how putting it on felt for the first time. Having a real job, making a real paycheck, living on my own far from Boston, and putting all of my ambitions out in the open was important for me to break free from my past and make something great with my life.

I felt that finally, there was one item I could wear and not feel self-conscious about how I looked, and I was ready to take on the world.

A great fitting and great looking outfit won’t gift you a confident character overnight however, and along your quest for confidence, mistakes will mount and other seemingly insurmountable factors will come into play, but it's important to keep moving forward. Confidence is built over time with consistent effort, mistakes, and risk-taking, but if you feel great in what you wear, you have more time to by .

Over the past few years, quite a few people have approached me about different aspects of my outfits, and after a long while, I thought it was time to put my tips out there in the open. I’m going to break them down by clothing category and explain in the context of my own outfits, but don’t worry. These are principles that apply to any gender, class of outfit (formal/informal/business casual/etc.), or budget. Remember: it's not about how much you spend, it's about how it makes you feel when you put it on. Let’s get started!

Bottoms

This is really where you want to start your routine. From my experience, the color and style of your bottoms are what guides the coordination of the rest of your outfit. I like to break down all color schemes into two categories: black or blue. I know that sounds odd, but consider that black and blue don’t mix, so if you choose navy pants, you’re not going to want to wear black shoes (the one exception is a navy suite with black shoes/socks), a black watch, black shirt, or black accessories. Similarly, if you’re wearing black pants, you’re not going to want to wear brown shoes, or a blue shirt. If you’re going the blues and browns route, they can combine great with most colors except black, and black is great with high contrast accessories, like whites, pinks, reds, and so on. Gray pants can also be a great choice, because they work with both black, and blues/browns.

The fit of your pants is also key. Make sure your waist fits, and if you’re at a new lower weight, then take in the waist. If you’re on the shorter side like me, opt for no breaks in your pant legs (this literally means that your pants are short enough so the fabric doesn't "break" touching your shoes). That can be tough to find off the rack, but altering your pant hem can be as little as $5 at your dry-cleaner’s or tailor’s and it will make you feel exponentially more comfortable.

Another common comfort problem, especially for the shorter ones of us, comes with the shirt tuck. Whether you’re a man on the short side or a woman with slightly wider hips, sometimes you feel like your shirt never stays tucked in, and that can get in the way of you feeling your best. The thing that will change your life: shirt stays. These are typically adjustable straps that clip the bottom of your shirt to your socks (if you wear socks). If you don't wear socks, this can be a rubber belt that’s worn on the inside of your pant waist to keep your shirt tucked in all day comfortably.?

Tops

Next is your top half. When you’ve decided what color scheme you’re going with for your pants, match your shirt’s color accordingly to what I mentioned in the previous section, but also don't be afraid to use patterns like herringbone, paisley, or something else you're fond of.

One thing that may stand out to you next in the mirror is mismatched styles. For example, if you’re wearing yoga pants, a nice sweater you wear for work may not look right to you. Opt for a casual or graphic sweatshirt, or v-neck t-shirt. If you’re wearing suit pants, you may not want to just throw on a sweatshirt. If you’re going casual, go casual. If you’re going more formal, stay formal. This kind of continuity also helps you to be sure of yourself!

Shoes & Socks

One of the most, if not the most important aspect of your outfit in terms of comfort and confidence is your shoes. Luckily, many people are already attuned to this fact. We all know that friend or have that partner (like mine) who’s obsessed with shoes. Interestingly enough, they aren’t wrong in their focus on having a great selection. If there is one piece of advice I can give on shoes though, it’s this:

It’s better to have two really versatile and great quality sets of shoes for $150 each than 10 pairs of cheaper shoes for $30 each.

Everything in terms of comfort and confidence in your outfit comes from a great quality shoe that’s well taken care of. They are worthwhile to repair unlike other shoes, and you are much more inclined to take care of them. This goes for sneakers just as much as it does for a set of wingtips.

If you love to wear funky socks, choosing your shoes can be an important decision. In most cases, you like to show enough, but not too much, so keep in mind how low or high the cut of your shoes is so you feel the best about how they look in combination with each other.

Accessories: Hats, Bags, Sunglasses, and Watches

I put these in a category together since your accessories are typically pretty versatile and are really the opportunity for you to have something of special significance or comfort close to you. In general, if you like to wear metals like rings, earrings, bracelets, glasses, or necklaces, try wearing all one color in your outfit. If you are lucky enough to have a great selection of costume or real jewelry, keeping the colors consistent with each other (all gold or all silver color) creates greater continuity in your outfit.

The same goes for watches and hand bags or backpacks. You don't have to have a Gucci bag or Rolex watch to look great. If you have a cheaper watch, but it works and the band is brown, it will look perfect when you match it with blue pants or brown shoes. Similarly, a black-banded watch will look sharp if you're wearing black boots or shoes, a black belt, or black pants. A silver or gray colored watch or bracelet can match with almost anything.

On a closing note, have faith that it's about fit and function over brand name or cost when it comes to your outfit, and you will be well on your way to feeling great in whatever you wear. Just and .

Need More Help?

Okay, okay. You knew you couldn't get through this without me mentioning ClothesOn, and you were right! But seriously, if your closet is a complete disaster zone, or you can never get a move on in the morning deciding what to wear, ClothesOn is there for you. Manage your personal wardrobe digitally, match outfits with one shake, and share what you're planning to wear with friends instantly so you have more time to by :

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