Wearing Dresses for Beginners

AFFILIATE DISCLOSURE: This post contains affiliate links. We earn a small commission from qualifying purchases.

Sharing is caring!

Some women are anti-dresses. To me they are the most comfortable things in my wardrobe and you don’t have to match a top and bottom! I writing about wearing dresses for beginners so that women will try out wearing a dress so that they can join in the bliss that is being female. One of the few things women can do that men cannot is wear a dress. Embrace your femininity and look slimmer!

wearing dresses for beginners


Rules for Wearing Dresses for Beginners

1. Make the dress fitted in the places you want to show off.

2. Sheath dresses work on almost everyone. Here is a great one.

3. Get a tailor. Not all women are the same on top as they are on the bottom. Buy to fit your largest part and get the remainder of the dress tailored to fit you. It is investment in looking great that does not cost as much as you might think. Add the cost of alterations into the retail cost and forget about it. If you have to buy one less piece to look great in the pieces you own, it is well worth it.

4. Belt everything. If your dress does not come with a belt, find a way to belt it! Drawing attention to your waist makes you look slimmer every time. I do  this all the time! (here with a button down dress, here with a summer dress, and here with an eyelet dress)

5.Smaller prints make you look slimmer.

6. Get great lingerie that fits. Also, pick up some Spanx or a girdle to slim yourself and make you look your best in a dress.

7. Wear color! Nothing looks better than wearing a bold color dress! Everyone has a LBD, embrace color and wear a little red dress or a little purple. What is your favorite color? Which color looks awesome on you? Buy a dress in that color! Yellow is one of my faves! If you must wear black, accessorize it with a statement necklace like I did here.

8. Don’t compete with detail of the dress. If your dress makes a strong statement, let the rest of your jewelry, accessories, and hair be simple and sleek.

9. You got to know when to  hold’em, know when to fold’em, Know when to walk away, know when to run! Know your body type and only show what you love and show only a little bit at a time. Never show cleavage and your legs at the same time.

10. Try the dress on with the shoes you will wear with the dress. Bring them with you when you shop if you can or buy from a store that carries the shoes you already own. If the shoes are not comfortable or does not fit properly, you will not wear them so don’t try them on with your new dress.

red-white-blue, wearing dresses for beginners


:: Outfit Details ::

Dress :: Banana Republic Navy and White Printed Dress (similar here)

Blazer :: Red Blazer from Banana Republic (similar here by Top Shop)

Bag :: Long Champ Navy Le Pliage Mini Tote (last worn here and here)

Bracelet :: Victoria’s Secret Yellow Enamel Bangle (last worn here  and here) (similar here)

Shoes :: Ralph Lauren Navy Snake Pumps (last worn here) (similar here in peep toe)

Disclaimer: I will receive a commission if you purchase from some of the links on this page. This in no way influences my picks.

Which rule do you already use in your wardrobe? Which one are you incorporating after reading this?

Sharing is caring!

20 thoughts on “Wearing Dresses for Beginners”

  1. Cute! I love all of your tips – you’re totally on the money, cannot stress how amazing a tailored piece is – it makes the cost so worth it!!!

  2. I love wearing dresses, and I always pair them with some sort of structured jacket or cute cardigan. I have a denim jacket that I love to wear with many of my dresses.

  3. I like the idea of wearing dresses with blazers. I on,y wear long skirts. I lime the selection you chose!

  4. Even though I’m in my 40’s, I’m a beginner with dresses and your tips are a great help. I do have a couple dresses I wear on a rare occasion and my favorite part is what you mentioned, not having to match a top and bottom. Pinned this to my fashion board.

  5. I’m just now coming into dresses in the last several months. I decided that a belt was definitely the way to go with some of my dresses yesterday but then the look didn’t come together so I’ll be on the lookout for a new one. Thanks for these tips!

  6. I am with you, I love, love, love the ease and simplicity of dresses. Plus they are cute and comfortable. I have everything from the little black dress to bright maxi’s and everything in between.

  7. I beg your pardon? You state one thing women can do that men cannot is wear a dress. Let me set something straight — my ID may indicate male, but that’s just the government’s way of saying the body belonging to the picture is equipped with a penis. I have lesbian parents and all sisters for siblings. I was part of the package when my sisters were adopted. I have been a female my entire life but have not undergone sex re-assignment surgery, nor have I used harmones or even makeup. I wear dresses, t-shirt athletic dresses, skirts, etc. all the time and I wear them well enough to generate quite a few compliments. So when you say men cannot wear dresses, even though I do not identify as male, with anything, you are basically saying you’ve lived your entire life hating what is unique or different and bullying others to bend to your bigoted and outdated views. The world of women should be ecstatic, welcoming and appreciative of so-called labeled males like me wanting to be a part of your world in a world where women are misused & abused and shoved aside because men think they know it all and control everything. I highly value a woman’s intelligence, which is too often disputed and they are never given enough credit. I value a woman’s opinion and presence and more of them should be in positions of power, from the civilian workplace and up into politics. I just want to be one, to live among you as one and be accepted as one.

    • Well, McKenzie Marie, this post was written six years ago, and I think things have progressed since then; don’t try to judge the past by today’s standards. I could tell you to, instead, go after the TERFs, but they don’t usually wear dresses, anyway. 🙂

  8. I am a man that loves to wear dress I love the feel and power of femininity witch overwhelm me in a way it is so BEAUTIFUL I can not stop or will not stop I will wear women’s clothes now for ever just be all you can be

  9. Lot of great ideas here. A lot to take in.

    Some of these might help me. See I’m looking to make the dresses I wear more masculine and less girly.

    I bet that doesn’t make sense. Now does it.

    See I like dresses, but don’t like feminine. Yeah, I am a odd ball. But hey that makes us all humans

    Thanks for sharing. Enjoyed reading it

  10. God created man and from that He created women. Why can’t males wear both kinds of clothing? Arab males wear long “robes”. It’s a western taboo that males can’t wear feminine clothing. I dare anyone from a western culture (ie: the US) to break from tradition an wear clothes that don’t conform with cluttered traditional norm.

    I wear dresses, skirts pants and anything I appreciate. I’ve never had any problems with anyone with my appearance. My biggest problem is what restroom to use.


Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.