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What Is The Single Most Attractive Outfit You Can Own?

When building up your attractiveness, it’s enormously useful to have a go-to outfit. For many of us, that’s going to mean a pair of jeans, heels, a blazer , and a bag you’re glad to carry.

Notice the flexible parameters.

Almost everyone can find jeans that flatter. Because those sturdy blue trousers have become a cornerstone of American culture, a version can be found for most shapes and sizes. Like boyjeans? Try Madewell. Flared? 7 for all Mankind Dojos are my current favorites. Skinnies? J. Crew or J. Brand or you name it. Same for heels and blazers.. I imagine a chant – stilettoed, blunt-toed, cropped, lapeled. Say it out loud. A stacatto of choices.

Go. To.

How do I know this is a go to outfit for attraction? Very scientific research. First, I cast my mind’s eye back over the years, and realized that whenever I felt the time had come to make my intentions clear to a man, I wore jeans, a white shirt, and pearls. (I note that this is the perspective of a straight woman, and would be interested to hear if there are similar lesbian go-to Attractive outfits.) Second, I reviewed Pinterest. Yep. One of the most prevalent outfits? Jeans, jacket, heels, bag.

Finally, a couple of years ago I wore this to meet young women blogger friends in Manhattan for the first time. Obviously I wished that they find me Attractive.

Of course,  some of us just don’t like pants. We don’t like the way they feel, the way they look, or both. How then to choose a go-to? Despite Pinterest’s fondness for shorts and skirts and maxidresses, I don’t think those are the most attractive solutions. I think it’s got to be a dress. One that allows for movement, but highlights your favorite bits.

Devastingly attractive, and still comfortable.

If you don’t care for pants, it’s quite likely you’re fond of your bosom, as they said in previous centuries. And somehow, with all that leg showing, I think you’re going to want to wear boots. For stomping around. For two feet on the ground.  There’s little quite so attractive as an effortless,  enthusiastic, authoritative stride.

You will notice, being the insightful lot that you are, a certain Sturdy quality to these outfits. Yes. That’s true. The single most attractive outfit you can own ties directly to your style archetype, whatever that may be.  But Sturdies are also quite likely to act as a net plus in your life, i.e., Attractive, so perhaps it’s not only my archetype preferences at play.

You may also notice some androgyny. My theory, until a better one comes along, is that gender testing is dangerous, even today, even now. And those who dare, attract.

Try a little daring. A little stomping. See what transpires.

57 Responses

  1. I’m going to go out on a limb here, but I do think that virtually all men love jeans and a white shirt. I think the first outfit is perfect, with the exception of the jacket. And here’s where I’m climbing out on a shaky limb – women love Chanel-esque jackets – men do not (unless they’re very quiet ones). I would change the 1st jacket (for a male/female date) to something else. Endless other choices, but I’d probably wear a motorcycle style leather jacket.

  2. I have no clue how to dress. Before cancer, when I was overweight by about 20 pounds I knew how to manage that. Now I have a stark contrast. No breasts, thin arms and chest. For a while exercise and weights were helping. But then I lost a bit of weight and more sagging. I have never enjoyed shopping for clothes, ever. It has always been a chore. My daughter on the other hand, can shop for designer pieces, mix and match and put together something new and perfect. I am clueless. Example, I once bought a leopard skin bikini. My daughter said, “What were you thinking?” I should take her shopping with me.

    1. Candy:

      I think you’ve found the solution already — shop with your daughter! I wish I had a daughter to go shopping with. Both my sons have a good critical eye, but they’re not interested in what I wear.

      Hang in there.

    2. Candy, I hope you come to enjoy dressing in this new mode. I am sure your daughter would love to help you. And the blogosphere would too, if we can.

  3. Love the jeans outfit. Not so much a fan of the boots with the second outfit. Something less engineer-like, maybe.

  4. The dress in the second picture down is too ‘mumsy’ so many of that style around here tends to look cheap,maybe the farmer’s around here would wear the boots!

    Am a newcomer to Giorgio Armani make up,especially the foundation divine on the skin.Ida

  5. I agree with the first outfit, although these days I’d go with a dressy flat, instead of heels. I also disagree with the jacket, but simply because it’s not my cup of tea – I’d don a nice blazer. Which is why I have a closet full of them.

    Pearls? Perhaps. I don’t own any; I should probably rectify that…

  6. Also, I do love dresses with tights and moto boots, but not that dress. Too baby doll or something. But love the boots.

  7. Jeans, well-fitting are fine, but a white shirt and pearls? I just can´t wear a shirt. I´d choose a blouse or knit with pearls. A bit of heel improves the posture. The way the hair is worn, matters. I don´t like jackets ( too masculine and ordinary ). Were it possible, I´d always wear a mid-calf length coat and yes a bag, but definitely one, which does not shout out its label.
    As to dresses, I like ones with a bit of drama ( as I wear them so seldom ). I´m not liking boots, as over here, they are a must most part of the year.

  8. Your post raises interesting questions. The nexus of social signaling, dressing to let a particular man know we are interested, being true to type, dressing to attract the type of man we find attractive – yikes!

    kathy (7:27 AM kathy) also raises the question of what items women may love, but men dislike.

    1. Lisa, sounds like you may have to deconstruct to the next level, ie. Attractive…to whom.

      Can the concept Attractive stand alone, without a qualifying prepositional after thought?

      Attractive to men never crossed my mind as being your intent in these Attractive essays. You and I were raised hearing our mothers say this or that was “good looking,” but there was never an ulterior Men Will Like You If You Wear That subtext. Perhaps it’s just a High WASP thing, but I can’t remember explicit or implicit suggestions that I doll myself up for men.

    2. Flo – the paragraph under the first Polyvore of clothing, mentions “attractive to a man, from the perspective of a straight woman”. I think Lisa’s intent was clear.

    3. Flo – no thanks needed. I think your question and point, raises a lot of questions and conundrums for most of us. I would love to hear Lisa’s take on the idea of dressing to be attractive to a man. I, for one, have a hard time wearing something (even if I like it) if my husband does not. What does that say about me? Not sure!

      1. Oh boy. That’s a big topic. I use myself as the first filter, him as the second.

  9. you are so right with outfit Nr. 1! Men like women that don`t seem to be complicated. Jeans, a white shirt and heels are just perfect to transport that. I found out that they are generally not fans of an empire line – first reaction might be: Are you pregnant? But as we don`t dress for men all the time – the second outfit is perfect for a girls meeting!

    1. I totally agree, and signed in to say that about empire dresses – a total turn off to men, unless of course pregnant.

    2. I had been thinking of the second outfit for someone more plus size, with a great bosom. Which would interest a man, I assume?

  10. Brava! Jeans, a shirt, and a jacket — the ultimate attractive combination, in my eyes. I know I look best with a collar and lapels. Sometimes I wear a white shirt as a jacket, unbuttoned, over a camisole or shell.

    But can’t we wear flats? I submit you can’t have a great stride in heels. I think a nice leather flat or better yet, a pair of flat riding boots, would look just as good, and then we wouldn’t have to have duplicate jeans hemmed to different heel heights.

    1. I used to favor flats but I find now that my comfortable heels actually work better for city walking. That said, if it’s flats for you, it’s flats!

  11. Your go to pieces are very similar to mine… Skinny jeans and whatever top, depending on the occasion is always a comfortable one for me… or a simple dress with ankle boots or flats…
    Isn’t it funny how we can have a million outfits in our closet… yet the same old ones are the ones that give us comfort and make us feel the most attractive… xv

  12. Mulberry bags stain in the rain, I had one for 5 weeks then sold it on Ebay, I once ran it to a butcher’s shop to ask for a plastic bag and then put my Mulberry into it – I can still remember the look the other customers gave me.

  13. Outfit number two tends to be my go to for lazy + attractive. I feel put together in a dress, and they tend to be flattering. Plus, they’re so fun to accessorize.

  14. I agree completely with the basic pieces but with a little tweaking given differences in one’s shape.
    But I agree that simple items, but of great quality, dressed up with a little jewelry is the go to look for attractiveness.

  15. When in doubt I wear a variation of outfit no1. I think men like it for variety of reasons, jeans suggest low maintenance, can do wonders for our behind and since men wear jeans and button downs they can easily picture how to get them off.

  16. So the Medieval Queen interest isn’t new.

    I’m on the lookout for pearl ideas. MIL left me a three-strand set of irregularly shaped ones that I recently re-found in a drawer. I’ve got to wear them so they’ll keep their soft glow.

    Next time a white blouse comes out, on they go.

  17. I have found that men like to see legs, not necessarily a mini- pencil skirt and heels. The jeans do show the butt, another area of interest. Could it be your choices are also geographically influenced?

  18. i just read an article last week that said the sexiest thing a woman can wear (according to a men’s magazine poll) was one of his shirts.

    my go to outfit always involves jeans.
    and i love the look of chanel jackets, the boxy shape just doesn’t work on me. but i have been told that a real chanel jacket looks good on everyone.

  19. I have worn skinny jeans tucked in boots with a variety of jackets since the 70’s. I am ready to change it up with a flowy dress with motor boots. It is just so easy and comfy to throw on jeans and not so comfy to throw on hose or tights with a dress. I keep telling myself I am going to add dresses to my wardrobe but have no idea what style. I do not like empire waist, or the wrap, or a shirt dress, and a sheath may look too board room with a blazer. At least you have inspired me to experiment in a new direction.

  20. Synchronicity indeed!

    The jeans/heels is right in my wheelhouse of the Attractive Uniform. In my twenties, I’d pair it with a slinky cowl-neck highlighting my shoulders and arms (and not my bosom, of which I am not fond). I’m moving more towards the look of outfit one for that same idea now, with perhaps a colorful cocktail ring thrown in to keep it fun.

    I love the idea of a dress with a boot, the yin/yang of that mix. My favorite night out frock at the moment is a mod vintage dress with low black alligator booties.

  21. Flo – no thanks needed. I think your comment raises a lot of questions and conundrums for all of us, and I would love to hear Lisa’s “take” on the whole idea of dressing to be attractive to a man.
    I know I often feel conflicted about the whole thing too.

  22. Very interesting! I am soooo tired of my good jeans. Have started instead to wear tasteful skirts with dark good quality tees and interesting shoes = instant attractiveness. You would not believe the attention from bus driver to ice cream vendor to young man to boss. And my guy, too. Ha.

  23. I really love that first outfit. The basic pumps would not work for me, but everything else yes yes yes … except I’d want that bag in a soft silvery grey.

    I so like jeans and a white shirt, and I am willing to bet lots of men like that combo, too. There’s just something about hiding our femininity under menswear.

    Although I adore jeans for holding everything in and hiding whatever dirt I might get myself into, my go-to, feel-good outfit is comfy, soft, peached chinos (preferably stone or putty colored instead of the requisite khaki), form-fitting white tee, bright navy single, breasted blazer with navy buttons (no brass for me, thanks), oxblood loafers with at least a 1-inch heel and no socks (I loathe socks, even in winter), and a tote (material negotiable, depending on time of year), in either a punchy color, like raspberry or something equally harmonizing but less obvious, like Wedgewood blue. Triple-strand pearl choker from grandma, small platinum hoops, sheer rose lipstick, lashings of black mascara, and my vintage faux tortoise Ray-Ban Dekko sunglasses, and I’m good to go just about anywhere. I realize the outfit risks sounding horribly preppy, but I try to add a little edge where I can, and you couldn’t make my corpse wear spouting whales or a pink/lime color-block combo.

    An alternative to the blazer is a structured cardigan with lapels and a heavy hand, like boiled wool … or the softness of cashmere or merino. Love them!

  24. I very rarely wear jeans trousers, on the other hand, I do wear a short, dark blue denim jacket, grey tee and shorter version of the pencil skirt ( knee length) as my to-go look with either ballerinas, kitten heels or pumps. European men ( though there are exception ) prefer to see the legs. There’s more mystery.

  25. Different go to outfits during different periods of my life. Right now, it would be a black knit jersey dress which shows my curves and legs–ultimately more flattering than jeans for our locale and my figure.

  26. If I am feeling happy with my body, I always feel beautiful in a dress or skirt. I love them but in Winter, I find the whole palaver of tights/layers a bit overwhelming.

    My uniform of sorts is always denim with blouses, slinky tees and if I want to feel powerful…a blazer or statement jacket. I used to shy away from this but now I think of it as elegant simplicity.

  27. So interesting reading the comments about what is attractive to men. As you know I’ve never been stylish and still don’t really get it but I’ve had wonderful men in my life since I started dating at age 16. All of the men in my life wanted me to wear jeans and a flannel shirt. That was their version of a sexy outfit! These days I get compliments if I wear jeans, a leather jacket and dangly earrings. What can I say?

  28. I think you cannot fail in jeans, crisp white oxford and jacket. With some fun shoes. I love it and I know M loves it on me, too!

  29. I like the first outfit very much, except for the pumps. I prefer jeans with flats or shoes with no more than a one inch heel.

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