How to Dress For Success Style & Fit Guide

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“Dressing well is a form of good manners”- Tom Ford

I ended my recent blog post “How to Dress For Success On a Budget” with this quote for a very good reason! Dressing well not only shows your respect for others, but for yourself. You can’t deny that when you look good, you feel even better. You cannot become the top notch successful business woman you want to become unless you dress for it.

While it may be obvious not to wear something that shows full-on cleavage at work, or a skirt that is so tight you can’t bend over without feeling like a can of biscuits about to pop- some things may not be so obvious. Here are some guidelines for fit to make sure what you have in your closet and what you decide to invest in that will keep you looking as professional as possible:


Dress Success Style Fit Guide

  • It doesn’t fit if it creases or “smiles” across the crotch of the pants. Nothing says “unprofessional”  like a groin area that’s smiling at you from across the boardroom.
  • Anything that is so tight that you have a panty line is a swift “no”.  While you might just need better underwear, the pants probably don’t fit hon.
  • Avoid extreme waistbands. Any waistband that hangs too far below or above the belly button (at least, unintentionally) — is a fit issue. It is important to add, that if you look like a sausage stuffed in a can or have a muffin-top, they don’t fit. If you’re having trouble with this an easy solution if to find pants that have a higher waist or just go up a size (there’s absolutely nothing wrong with that!). Also, make sure there is enough room in the waistband to tuck in blouses or tanks comfortably.
  • Check the length of the crotch. If you can see the outline of your lady parts through the pants (aka “camel toe”), your pants are too tight. Alternatively, if you can grab a handful of fabric between where your body ends, and your pants begin, your pants are too loose.
  • If you can’t at least pinch an inch of extra fabric on your thighs, your pants may be verging toward “too tight.” You may find that they wear poorly (they may be busting at the seams a pig in a blanket) and the fabric may get thin in certain places.

Blazers & Cardigans

Dress Success Style Fit Guide

  • The shoulder seam of the blazer should hit right about where your shoulder ends. If it falls closer to your neck, it’s too small. If it juts out over where your shoulder begins to slope downward, it’s too big.
  • If we are going off the old school guide for fit, “a  full-length blazer sleeve should hit just a little bit above the top joint of your thumb if you’re standing with your arms at your sides. Your wrist itself should be covered. “ Millennial women have a bit of leeway with this rule since women’s suit are currently evolving. If you are wearing a more modern style (i.e., no collar), you can get away with the sleeves hitting your wrist bones. Wearing a blazer like this will make your arms appear to be smaller than what they are by drawing the eye to the thinnest part of your arm.
  • A blazer that fits properly in the bust will cover about half of each breast (measured from vertical outside working in toward the navel) and skim over the covered area without bunching or wrinkling. Ideally, it should fit beautifully both buttoned and unbuttoned.
  • You want the blazer to follow the natural curves of your body without pulling or sagging. If you’ve got wrinkles at the sides or across the back, the blazer is too small in the torso. If you’ve got gobs of extra fabric around your midsection, the blazer is too big in the torso.


Dress Success Style Fit Guide

  • Skirts should hit right above or below your knee, anything shorter than this is too short, and anything longer than this is too casual.  I’m 5’10, and if I can find skirts that fit, so can you.
  • If it is tight enough that you can wear it to a club and look “sexy”, it’s a no go for work. Alternatively, if you’re fighting to keep it up all day and it’s sliding around all over your body like a tilt-a-whirl at the fair, it’s too big.


Dress Success Style Fit Guide

  • Real life is not Tumblr. While you may be inspired by the tight (sometimes short) dresses “working women” wear on the popular social media platform, in real life they are not appropriate for work. The same rules for skirts (length/tightness) apply to dresses, but also rules for pants like “no panty” lines apply.
  • You should never wear a two-piece dress ensemble to work (even on Tuesdays).
  • This next one should be pretty obvious, but you’d be surprised at some of the stuff I’ve seen…. Your dress should not be backless or have a cutout of any kind.


Dress Success Style Fit Guide

  • Anything with an open toe is not  considered professional. There’s some wiggle room here depending on where you work or what your job title is. Regardless, your job is not the place to show off your wicked lime green pedi.
  • If the heel is higher than three inches, it is not appropriate for day wear in general. Save them for a Saturday night out with the girls because you’ll need it after your long work week.
  • Make sure they are comfortable and can walk in them without looking like a newborn mare. Nothing seems more ridiculous (or undermines your power) than hobbling around in your shoes because you have blisters or can’t balance.


Dress Success Style Fit Guide

  • Nothing will ever beat the timelessness of a classic button down… unless your breasts look like they are trying to escape BDSM style bondage. Your blouses should not pull across your chest, and there should be enough extra fabric to be able to tuck them into your bottoms comfortably.
  • Sheer blouses are totally fine as long as you can: 1. Wear a tank under them 2. Can’t see your bra. If not, then it’s not “fine.”
  • Sleeve length is another gray area in work wear because it depends on where you work or what your title is. The best rule of thumb is to make sure your sleeve is the width of your hand on your shoulder, if it’s not, then it’s probably not appropriate. Stay on the safe side and bring an appropriate blazer or cardigan to work with you.
  • Solid color blouses are always your best bet! If you want to go with a print, make sure it’s not too crazy or inappropriate.


Dress Success Style Fit Guide

  • If you look you best, you’ll feel your best. Take a little bit of extra time on your appearance in the mornings whether it’s taking the extra time to moisturize or put on a full-face of make-up. While there is nothing wrong with wearing little to no makeup, make sure you are always putting your best self forward. On the flip side, do not show up to work with Garcia-esque from Criminal Minds makeup.
  • Your hair should not always be slapped up into a quick pony or look like you woke up 30 minutes past your alarm and literally had to roll out of bed into work. Take some extra time to make sure your hair looks neat and professional.
  • Very few things make you feel like you have your life together more than a fresh manicure. Just make sure that your nails are not a color, length, or design that would distract your boss while you’re trying to have a conversation with them about that raise you deserve.

Look like champagne on a sparkling cider budget. Check out my “How to Dress For Success On a Budget” to get tips and tricks for shopping for work wear on a budget here.

Do you have any style or fit tips? Let me know in the comment section below!

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About Chloe

Chloe is a San Antonio, TX native who loves margaritas and brunch almost as much as she loves reading a good book and a catching up on Empire. Learn more about Just a Girl in This World, click on the "About" tab in the main menu.