Lost Password?

A password will be emailed to you. You will be able to change your password and other profile details once you have logged in.

Hot Midi Pencil Dresses for Day or Evening

by Tina Boomerina (Christina Gregoire)

midi pencil dressYou don’t have to be shaped like a pencil to wear a midi pencil dress. Actually, it’s better if you have a few curves… like the kind Sir Mix-A-Lot liked when he could not lie… like a booty. Well, it also helps to have hips and thighs, like a pear. And, it’s okay to have boobs and hips, like an hourglass. And, it’s even okay to be a plus size. Really.

It’s a little tougher to wear a pencil dress if you’re an apple shape, so those of you with tummies like mine are better off wearing stretchy pencil skirts with a flared or slouchy top. That way you can balance your silhouette. But, as for the rest of you… you women with pear or hourglass curves… there’s no reason to think that body-conscious midi dresses are just for skinny teenagers who hang out at Forever 21.

Sexy Long Pencil Dresses

long tight dresses are sexy

Some slinky midis should be reserved for parties, bars, cruise evenings, and dinners at tony restaurants because they are way too hot for daytime. But, the dresses I’m talking about are the types of dresses that accentuate every curve and bulge of your body. (Imagine an Asian Vargas Girl in a too-tight dress… or a racy Sailor Jerry Tattoo.)

However, I don’t care how old you are, if you’ve got the right curves to pull off a long, tight midi dress and you know how far you can go without sliding into slutsville, I say, “Wear it and own it.”

party evening dresses with sleeves for older women

A pencil dress is a very sexy look that’s tailor made for older women, because many of the dresses don’t show much skin. You can even find styles that cover your jiggly arms and your saggy necks… and still make you look hot, hot, hot.

Plus Size Midi Pencil Dresses for Evenings

If you’re heavy… Wait… Let’s rephrase that... If your body has an abundance of very curvy curves, you have to really look at your pencil dress from all angles before going out in public. However, why not do a total Kim Kardashian and make the most of your assets. Life’s for living, baby.

However, many pencil dresses are very stretchy. If you’re a bit chubbier or a bit older, you should check around to find something in a fabulous fabric… something that makes you look sexy, but not so sexy that people think you’re moonlighting when you’re walking down the street. Lace is one fabric that might give you the look you want. Jacquard, a non-stretchy fabric, is another.

Daytime Pencil Dresses for Work or Play

Believe it or not, there are (semi-sexy) pencil dresses that work for daytime. Yes, you can even wear them to the PTA or the garden club. It all depends on the:

  • Fit
  • Fabric
  • Cut
  • Neckline

The Fabric Makes a Real Differencesexy pencil midi dresses for daytime or evening

If the fabric is only as thick as opaque pantyhose, you probably shouldn’t be wearing that dress for day or for evening… if you know what I mean. Even if you wear several pairs of Spanx thingies, your ta-tas and your no-nos are probably going to show through. And, that’s inappropriate for any time of day or night, no matter how high the neckline, no matter how dark the room, no matter how small the gathering… unless it’s “that” kind of gathering.

If you want a midi dress that you can wear to work (or school or the grocery store), look for material that is heavy enough to hold you in, to cover your unmentionables, and to keep you looking presentable. You can find flattering pencil dresses in fabrics like cotton blends or denim, both of which are absolutely perfect as daywear.

The right patterns, prints, and textures can also make a slinky dress into a daytime dress (or a multi-tasking dress that can be worn day or night). Pencil dresses with color blocking are often intended to be worn as workwear.

The Neckline of the Dressmidi pencil dress skirt

Some pencil midi dresses are very revealing, with cutouts everywhere and cleavage enhancing necklines and whatever else designers can conjure up. If you’re young and skinny, you might need these things to stand out from the crowd if you’re in a competitive world like LA. However, if you’re older or extremely intelligent, you should pay more attention to the neckline on a pencil dress than you would with another type of dress.

I don’t know why, but a pencil midi dress could be made of thick carpet and people might still view you as Jessica Rabbit… so if you’re curvy, don’t go overboard in the sex-appeal department. Try to avoid plunging necklines and slits to your hoo-ha.

I Would Wear a Tight Midi

If I had a booty… or a tush implant… I would wear one of these dresses. There’s something so exotic about midi pencil dresses that makes me mesmerized by them. I can’t stop staring at stars who wear them. I’m so jealous. And, if you have all the right curves, even if they are plus-sized curves, I’m jealous of you, too, you lucky girl.

More Fashion Articles for Boomer Women Over 40, 50, 60:

Beach Cover-Ups for Women: Plus Size Tunics, Dresses, Caftans, Sarongs

Should Older Women Wear Bright Colors? Fashion Over 50

Two Piece Swimsuits for Women Over 40

Women's Travel Cruise Wear Online: Chicks Over 40 or 50

Photo Credits: Prshots.com.

Main Photo: Asos.com.

What do you think of this article? Would you wear a long, tight, sexy dress? I would... if it fit. Leave a comment at the bottom of the page or give us a Google Plus.

Tina Boomerina (AKA Christina Gregoire) is a Baby Boomer born at the end of 1952. Her mission is to make the internet a kinder and gentler place for Baby Boomer women around the world. Tina's specialty is fashion for women over 50.

Follow Me on Pinterest Follow My Boomer Lifestyle Blog on facebook

Related Posts


  1. kay kerns

    This is one style I feel too heavy to wear But I like a stretchy skirt with a loose top

    • Tina-Boomerina

      Kay, I am not sure I can wear it either, but I saw one dress that had ruffles in all the right places. It's tricky, but I think I could wear it if it had ruffles or a peplum.

      Tina Boomerina

  2. Emory

    It's hard to find your website in google. I found it on 17 spot,
    you should build quality backlinks , it will help you to get more visitors.
    I know how to help you, just type in google -
    k2 seo tricks