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Career Dressing: Older Model Cougar. Wut?

Career Dressing: Older Model Cougar. Wut?

I was a super homely kid in grade school and high school, and then 80s perms didn’t help. So maybe one of the reasons I don’t mourn my fading looks as I approach 50 is that I never had those kind of make-ya-look-twice looks to start with. In fact, I look much better now than I did as a weird little fuzzy-headed whippersnapper.

I know my mom wants me to sit up straight, but my legs are too short for this chair ๐Ÿ˜ฎ
The Deets: Loft Dress (Loft flash sale); Miz Mooz Tillman Pump (Amazon); Luxury Lane stretch belt (Amazon); Shrug (old, maybe Marshalls); Brooch (antique); tights (oh man I wish I remember because I want more, knowing my limited retail habits, Marshalls or Target)

But recently it has been brought to my attention that I do have some kind of power over the occasional male, provided he’s more than three decades younger than me. (Man, that’s like three decades too late. Where were you when I needed a prom date, kiddos? Not conceived of yet? Puh-leeze.)

I got an exciting phone call today. Can you tell?

Mostly by The Teen who advised me this week it’s embarrassing when her friends say her mom is hot. (I’m all, “Really, do spill,” and she’s all, “Shut up, you’re still embarrassing me.”) And then by a smokin’ hot hottie who leaned over and whispered in my ear that he really liked my sexy voice. I believe this encounter was rife with possibility except I love The Absent Minded Professor, and even if I was available, I would like to stay out of jail.

It’s like my love of Mary Janes and booties hooked up and had baby shoes.

So that’s why my heels have gotten a little higher and my skirts have gotten a bit shorter recently. ‘Cause I’ma Older Model Cougar.


Seriously. I just studied hard on the rest of you style blogging beauties, and realized that above the knee skirts are flattering on many women, especially shorties, and so are comfortable heels. And a really wide belt helps me fake a waistline.

This post was brought to you by the outta control Prince channel on Pandora ๐Ÿ˜› If you’re interested, we’re hyped up on the musical stylings of Jackie Wilson, Janet Jackson, Carl Carlton, Louis Armstrong, and John Legend. Wanna feel kinda cougar-ish yourself? Jam to a little “Nothing Compares 2 U,” Prince’s live version.

33 Responses to Career Dressing: Older Model Cougar. Wut?

  1. Oh My Gawd, I melt for that song by Prince. Thanks for the reminder. You look gorgeous, natch – and I was just discussing with my own beloved mate tonight that very old men still want to buy me drinks . . . and some very young computer programmer types too! He said, "Oh, they just like any woman who'll talk to them". Thanks, honey!

    • Patti, in light of my advanced age and looming Bucket List, I looked up Prince concert dates right after I finished the post. None pending. Shoot.

      At least your admirers CAN buy a gal a drink…lol. You reminded me about a decade ago, before I met AMP, an older neighbor helpfully suggested I go with her to local VFW dances to try to meet men. Ouch.

  2. Lol, I hear ya – I was never a stunner when I was young, oh woe is me, but I get much more attention now that I'm older and put myself out there more! I have to say I love it, but like you, I love my L. But so good for the old Cougs' egos, eh?

    The outfit: ooh, those shoes, are bondage-tastic! Fabulous. Love those bright colours on you and yay for above-the-knee skirts (said the chick wearing a below-the-knee skirt).

    Keep an eye on your mailbox – I sent you a prezzie. ๐Ÿ™‚

    • Ooooh, that will kill Th' Teen, if I tell her my shoes are bondage-tastic. She'll never let me be seen outside of our vehicle at school ever again ๐Ÿ˜›

      I can't imagine you ever being anything less than a stunner, but some of us are just late bloomers! Prezzie! Cool! I have something for you I must get mailed before Sasha Jane puts bite marks in it….

  3. Love the outfit! Can't imagine you not being as cute as you are now!!

    Isn't it a bit fun when the teen is embarrassed???? Payback!

    I had big boobies in high school (and smaller everywhere else). I don't think the guys realized I had a HEAD!!!

    • When I was about 35, someone who'd only known me for a short time, upon hearing what an uber-nerd I was in high school, said, "but I thought for sure you were a cheerleader!" When I asked whatever made her think that, she said, "Your teeth are so straight." Yep, it's all a matter of perception…:o

      Bless your heart, Tamera, you had what we all wanted in high school! ๐Ÿ™‚

    • Thanks ๐Ÿ™‚

      They come in three other colors and I'm struggling with the awful first world problem of explaining to myself why I should only have the one pair :/ As part of the negotiations, I am almost ready to give up all my other shoes in exchange.

  4. Love the shoes, love the belt, love the shrug, love the sentiment, love what Sheila said about the shoes (bondagetastic! Naughty.). You look great in that outfit – purple is a great color for you!

  5. Awww those shoes!! So so amazing. My slim little feet cry out for such strappy goodness. Honey, you are so gorgeous. Some folks just get betteh with age.

  6. First of all, it would not surprise me in the slightest that men hit on you! You are a knock out lady and don't you forget it! And the Prince station sounds like a good one to jam to. I love purple on you. Seriously. I'm glad you've been wearing it recently because it is perfect on you!

  7. RRRRRAAAAAOOOOOOOWWWWWWWWW!!! That's me roaring Cougar-style at all those starry-eyed young bucks eyeing you up – yeeeeeaaaaaaaaaah!!! What's not to LOVE in these pics? Nothing that's what!!! Baby shoes – hahaaaaaaaaaa, oh yes they are the perfect shoes and look at those gorgeous tight but DAAAAAYYYYYYYAAAAAAM woman, you are killing the purple frock you gorgeous, gorgeous creature! Thanks so much for your lovely comment on my bikini reveal – you're simply wonderful and never fail to make me laugh:)) xoxox

  8. I take whatever compliments I get nowadays since they are few and far between. I used to thrive on that when I was younger but now although it is a definite ego boost (I haven't lost *everything*) it kind of makes me uncomfortable. If I get whistled at I sort of look around to see who is beside me.

    I love the whole outfit and those shoes and tights are wicked.


  9. Seriously! So hot! I've also embraced the shorter skirts and higher heels. The fact that it coincided with my separating from my husband is in no way connected. ๐Ÿ˜‰

  10. I don't doubt that men (of all ages) find you irresistable now. You're a fox.

    Life is funny. I wasn't especially attractive when I was young — and I cared about it then. I couldn't care less now and women tell me I'm attractive. (Not that I believe them.) Sounds like you have similar experience.

    It's great that you're emphasizing your beauty with your fashion choices. Make the most of it!

  11. You look great in that! Those shoes are fantastic, too. I love how you use the wide belts to fake the waist. I just haven't had as much luck with that for me.

    I think older women are sexy because we have self confidence and know how to strut what we've got. I was so insecure when I was younger that I had a very hard time even talking to boys. Thus, my lack of dates in high school. Oh yes, and those 80's perms did not help!

  12. You ARE a cougar in the best way Lynne! And I have decided I want to be you when I grow up cause I'm not going to stop being fashionable either! And age is just a number anyway!!

  13. Two days in a row and you are looking SPLENDID in Purple Dresses. I love the mixture of two purples here between the sheath & the shrug. Also, awesome vintage brooch & cool OBI belt. But what is even more awesome is those tights & shoes. I agree on your description of Mary Janes & Booties having a baby together lol.

    This outfit & the one from yesterday in particular, prove that YOU STILL GOT IT and yes you are a Hot Mamma but your teenage daughter shouldn't feel embarrased. By the way, I never knew you were petite. You always look at least about 5.7 feet tall. Your legs are so long. How tall are you Lynne?

    P.S. Love that first photo of you stting on the chair.

    Take Care, Ada. =)

  14. Ha, Lynne the Cougar, hear her roar! Why wouldn't young men think you are a fabulous hottie? You ARE! Confidence, friendliness and warmth are big factors in attractiveness, and you have those in abundance, and a killer figure and great style to boot. Never heard you speak, but if the young man says you have a sexy voice, who am I to disagree?!
    You look fabulous in purple in your multi-strapped shoes.
    I agree about the looks thing, I was never pretty so I think ageing isn't so much of an issue for me, I don't have any looks to lose! I make use of what I have, in a way that I entirely failed to do as a teen/young woman, and have a confidence that the younger me would have envied. It's all smoke and mirrors, I reckon – act like you're a goddess and people often agree! And you look like one to me, so there! xxxx

  15. Love these pictures, Lynne. My gosh, those shoes, those tights… Those legs! You are beautiful.

    It all comes down to confidence. I am so so much more confident and happy in my skin now than I was 10 years ago.and people (menfolk, but ladies too) pick up on this.

    Work it.

    I am pleased you have embraced the shorter skrts too – with a patterned tight and funky shoe, a bit less skrt length just looks right.

  16. Agreed with Shybiker–you ARE a fox! Purple is such a knockout color on you, lady. I was dorky as a kid and I'll probably be dorky 'til I die, and I've never been complimented much for my looks (other than when I was living in Santa Cruz and had my four-color hairdo–then people would just walk up to me on the street and ask if they could touch it), but I guess that also means I don't feel much pressure to look sexy or gorgeous or whatever, and I just have fun with my clothes!

  17. I can't imagine you anything but gorgeous, as you are in the photos above. I'm not surprised that you have the attention of men of any age.

    The purple dress, belt, brooch, shoes and tights create a stunning silhouette!

  18. I simply can't picture you as NOT just totally beautiful as now – you are stunning! What awesome saucy feedback – congrats on a smokin-hot Cougar Era! Today's outfit is just gorgeous. I love it all, the colours, the shrug/dress/tights/EXCELLENT shoes, perfect mix of softness and edge. Fab photos. ๐Ÿ™‚

  19. LOL! love this post! and you look absolutely great, and I totally identify with being the ugly duckling who feels a bit better about who she is these days.

Contact Info:

Lynne J. DeVenny, N.C. State Bar Certified Paralegal

Owner & Virtual Paralegal, DeVenny Paralegal Services

Email: lynne.devenny[at]

Telephone: 336-582-0003

Inquiries are welcome, with free quotes available.

Meet Lynne:

Lynne DeVenny is a North Carolina State Bar Certified Paralegal with over 27 years of experience working on complex litigation cases, including medical malpractice, personal injury, workersโ€™ compensation, and Social Security disability.

Disclosure: I am not a lawyer and cannot provide legal representation or legal advice.

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