A Quick Guide to Dressing Up

The other day I went for a walk with my dad, and as we walked we ended up talking a little bit about clothing. We were walking along the beach and it was a slightly chilly day, and so most people were wearing casual clothing, however some young women were wearing outfits that I would associate more with clubbing or partying than a midday outfit. My dad pointed this out to me, and I brought up that I’ve seen this happen in other contexts as well, usually as a way of ‘dressing up’ for an occasion rather than looking too casual.

I explained to him that the concept of formality and dress codes were never really taught to my generation, at least in my experience, so it makes it difficult to know how to dress up an outfit while still looking dressed for the event you’re going to. This is something that I’ve personally struggled with a lot, so I thought I might write a quick guide to it.

What is dressing up?

To start, let’s just get the definition of dressing up out of the way so that we can make sure that we’re on the same page for the rest of this post. Dressing up is something done to make an outfit look more formal. This can be done using makeup, accessories, hairstyles, and swapping out pieces of clothing for more formal versions.

Essentially, dressing up is the opposite of dressing down (I might make a post in the future of how to dress down without looking sloppy or under-dressed).

The number one mistake with dressing up

The biggest mistake I see young people making when it comes to dressing up is that they end up wearing an outfit of a different nature for the event they’re attending or activity they’re doing. I think this comes from the thought process of outfits for different activities existing on a scale of least dressy to most dressy, so they think that the way to look dressier is to wear an outfit for a dressier activity.

Least formalSemi informalSemi formalMost formal
Gym outfitSchool outfitBusiness outfitParty outfit
Simple outfit formality scale, with least formal on the left, most formal on the right

I’ve done this myself. I’ll never forget the two weeks where I wore business casual outfits every day (except Fridays) as a teenager. I was doing a couple of week long events at a university and decided to dress up for my first day there (by wearing dress pants and a blouse, naturally), and everyone else was wearing casual outfits (jeans, shorts, t-shirts, etc). Not wanting to seem like I was trying too hard I basically doubled down on wearing business casual looks. Hey, these people didn’t know me. As far as they knew this was how I dressed every day of my life.

Honestly, it made navigating the city on my own much easier, because I blended in with the crowds of adults who were going to actual jobs, but I definitely stood out while on campus.

However, from the experience I’ve gained from writing about fashion and working in styling, the way I see the formality scale has changed. Rather than seeing it as a scale of least dressy to most dressy with certain looks for activities falling on the scale like a number line, I’ve realized that it’s more like each activity or event has its own scale of least dressy to most dressy, and you need to go up the scale for the event you’re attending or activity you’re partaking in, rather than jumping to a different event or activity’s scale.

Outfit t typeLeast dressyModerately dressyMost dressy
Casual outfitSweatpants, hoodie, sneakersJeans, hoodie, sneakersJeans, pullover, sneakers
School outfitJeans, t-shirt, sneakersJeans, t-shirt, flatsDress pants, t-shirt, flats
Business outfitDress pants, blouse, flatsDress pants, blouse, dress shoes/heelsPantsuit, blouse, dress shoes/heels

If that doesn’t quite make sense to you yet, that’s okay. I’ll give a small guide to how to dress up outfits for different occasions, so that you can understand how this works in practice.

How to dress up…

a casual outfit

So a casual outfit. Let’s say it’s a pair of medium wash jeans (the cut doesn’t matter too much, just whatever you feel comfortable with), and a t-shirt. How do we dress this up? There are a few ways.

1. Change the color of the jeans

It’s an unwritten rule that the darker your jeans, the more formal they are. So in the scale of jean color formality (never thought I’d write those words in that order) it goes, from least formal to most formal, white, light wash, medium wash, dark wash, grey, and black. Colored jeans don’t count because it’d be too complicated to add those into the scale. If you wear colored jeans, congratulations, you exist outside the realm of formality and probably look amazing doing it.

2. Add matching accessories

My favorite way to dress up an outfit is to add some accessories. For a jeans and t-shirt outfit, I’ll usually go for a belt, some nice flats or boots (depends on the weather), and a hat. The accessories don’t necessarily have to match the jeans and t-shirt, as long as they coordinate with each other. Also a good pair of sunglasses can do a lot of the work of dressing up an outfit, trust me.

3. Makeup

There is one very simple, very easy way to use makeup to dress up an outfit. Put on red lipstick. Yep, that’s it, just some red lipstick will instantly dress up any outfit. The key to not looking weird in red lipstick is finding the shade of red that suits you. For years I made the mistake of going with a red that’s too light or bright because I have pale skin and I felt like anything else would be too dark. But it turns out my best red is a deep one, and it doesn’t look odd, even if I wear it without any other makeup.

a school outfit

Don’t worry, I’m aware of dress codes surrounding many school outfits. I won’t assume that crop tops, tank tops, or mini skirts are your go to school outfit. Instead let’s say that your school outfit is a pair of jeans and a hoodie. Nice, comfortable, and warm! Here’s how you can dress it up:

1. Swap out the hoodie for a knit sweater

Rather than wearing a hoodie, a good pullover will keep you just as warm and will make it look like you put more effort into your outfit. While a simple, solid pullover knit in a stockinette stitch will always be a classic, you can also go with something with an argyle pattern, or a cable knit for a slightly more academic look.

2. Upgrade your shoes

Sneakers are probably a go to choice for most students, but they are a more casual look. If you don’t have to do a lot of walking then flats or low heels can be a nice feminine choice. For a sturdier shoe, you can go with a loafer or oxford.

3. Style your hair

Another way to dress up your look is to style your hair. It doesn’t have to be anything elaborate, just something different. A sleek ponytail can give a serious look, a claw clip twist can look elegant, or if you hair is short try using an accessory like a barrette.

Something that I’ve gotten into recently is hair rollers! I’ve been setting my hair in them every night that I wash my hair, and it’s been challenging, but fun.

a business outfit

For the business outfit, I’m going to assume that you’re wearing dress pants, a button up, and a blazer. Here are a few ways you could dress up this outfit:

1. Wear a matching set

The first way to increase the formality of the outfit is to wear a matching suit set rather than separate dress pants and blazers. Generally, the darker your suit is, the more formal it’ll look (like with the jeans in the casual outfit section). The same goes for shoes, so keep that in mind when choosing your footwear for the day.

2. Add jewelry

Adding a little bit of jewelry to your outfit can be a subtle way to dress it up. Your jewelry doesn’t have to be super ornate or flashy, even just a pair of earrings will add a little bit of shine to an outfit.

3. Put your hair up

While all sorts of hairstyles are generally accepted in the workplace, hair that’s styled or tied up is usually seen as more put-together than hair worn loose and down. A bun can be a simple way to put your hair up for work, or doing a half-up style to frame your face can look very elegant with the right hair clip.

If you wear a hijab then obviously this tip doesn’t quite apply to you, so what I recommend is making sure that your hijab matches the colors of your outfit. Matching it to your shirt can create a seamless look, matching it to your blazer can add contrast, and matching it to your accessories can add a bit of fun to the look.

a formal outfit

Let’s say that for a formal event you’re going to be wearing a tea-length dress with a baguette bag. Here’s a few different ways to potentially dress up the look.

1. Increase the skirt length/coverage

In general, the longer and more full-coverage your skirt is, the more formal it looks. Floor length looks more formal than tea-length, no slit is more formal than a thigh slit, and a sheer floor length skirt looks less formal than an opaque tea-length skirt.

2. Add texture

A fabric with a unique texture that captures the light will add a level of lavishness to any outfit. Velvet can look rich, satins and silks add shimmer, and tulle creates an ethereal or weightless look. Figure out what your favorite texture is!

3. Scale down your bag

Rather than wearing a baguette bag, something smaller such as a clutch can dress up a formal outfit. Generally the smaller your bag, the more dressy it looks. Clutches come in a variety of styles and motifs, despite their small sizes, so you can find one that reflects your personality or interests!

So those are some different ways to dress up some different outfits!

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