How to Dress Like A Grownup, Part 1: Where to Start

Hey, you over there, the one who’s made it out of college and into a so-called “real” job! Yeah, you, the smart, hardworking, successful one who still has no clue what to do about your wardrobe. This post is the first in a series that’s just for you, because what’s perfectly appropriate to wear to class at 19 doesn’t work ten years later. And neither does copying what your parents wear, because no matter how well they dress, they’re not you. Through this series, I’m going to take you through the basics of putting together a wardrobe that includes options for just about every occasion you’ll encounter, including the basics of fit and color, what to keep, what to toss, where to spend a little more, and where you can cut corners.

Let’s start with what you already have. There are some clothes that it’s OK to wear, if you’ve got good basics. Others have specific purposes and shouldn’t be worn for anything else, and some…well, feel free to keep them if they have sentimental value and you can’t stand to get rid of them *peers at stack of well-worn concert and event t-shirts* but you really shouldn’t go out in.

Things you need:*

  • Straight leg or boot cut jeans in a length that doesn’t drag the ground at the heels
  • Solid color t-shirts
  • A couple of button-up shirts or nice blouses in colors you’ll actually wear
  • A couple of sweaters
  • A jacket
  • The shoes recommended in my Shoe Shopping Decoded post
  • Socks, underwear, etc, that fit right and are in good condition
  • A couple of pairs of dress pants
  • A pencil or slight A-line skirt, if you wear skirts
  • At least one dressing-up outfit, whether dress or suit/tie

*This is a minimum list. Feel free to have multiples of each item.

Things that are only for specific purposes and shouldn’t be worn otherwise:

  • Swimsuit coverups/swim trunks are only for the pool area.
  • Gym clothes/shoes are for workouts only. Especially if your sweatpants sag and make you look like you’ve had a toileting accent, or are so tight that you have a visible panty line.
  • Pajamas and bedroom shoes–these stay in the bedroom! Really!
  • If you paint, or if you dye your hair at home, keep a shirt that’s already splattered so you don’t mess up another.
  • Club clothes are OK only if you’re actually out clubbing. And even then they’re questionable.
  • Camouflage is only OK if you’re on a hunting trip or a military assignment at the moment you’re wearing it. Don’t wear it in public!
  • Snow boots are only for snow, rain boots for rain, etc.

Things to never wear again:

  • Anything with rips, holes, stains, or tears
  • Anything see-through from wear, or a different color from what it once was
  • Anything so short your butt hangs out, or that shows your underwear
  • Anything that you haven’t worn in a year or more–you won’t miss it!
  • Anything that sags, gaps, or is otherwise too big
  • Anything you wore with an ex, especially if they broke your heart–you’ll never be happy wearing it again.
  • Any pants with elastic waists (unless you have a medical condition that makes pull-on pants a necessity), tapered legs, or pleats
  • Anything fur (fake or real–it’s tacky)
  • Anything in an unflattering color–your coloring is what it is, and no amount of “but it’s so cute” will make the color work on you.
  • Anything left over from high school
  • Pants or leggings with any kind of print on them
  • Anything that hits between your knee and your ankle–that’s a universally unflattering length, whether dress, skirt, long shorts, or capris

Just realize that it’s OK and necessary to purge your wardrobe. There’s no reason to have clothes that don’t work for you and that don’t represent where you are in life and where you want to go. In the next installment of this series, I’ll talk to you about fit and how to tell if something works on you.

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2 thoughts on “How to Dress Like A Grownup, Part 1: Where to Start

  1. It might also be worth mentioning that a snuggie is not appropriate work attire. The new hires in the call center either dress way too casual or wear their nightclub attire.

    Wear a warmer sweater and accent with a scarf if cold. Platform stilettos in cherry red, never a good choice for the office.

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    1. The stilettos by themselves, as an accent to an otherwise conservative outfit, aren’t bad. (Unless they’re glittery and sparkly and higher than the person can walk well in, or a stripper-style exposed platform, in which case they’re not appropriate anywhere.) It’s when the rest of the outfit is similarly flashy that it’s tacky and inappropriate.

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