Styling Tricky Accessories

Friends, you know that the phrase, “shouldn’t wear that” gets my dander up, right? It totally does. I believe that women should wear clothing that makes them feel gorgeous and happy, and that style rules should be applied on a case-by-case basis and, even then, merely as guidelines. Wear what you love, the rest will fall into place.

But I realize that it’s often easier for me to SAY that than for you to DO it.  With all the magazines and TV shows yammering at us that we shouldn’t wear certain items if we’re shaped a certain way, and how some garments and accessories are “tricky” to pull off, it becomes difficult to maintain confidence. After all, these folks are experts, right?

They are. And although their presentation of these rules as hard-and-fast drives me batshit crazy, the underlying guidelines based in maxims of traditional figure flattery can be useful. Especially if you are striving for a tall, slim, proportionate, mildly hourglass-y figure when you dress.*

So I thought I’d tackle a few “tricky” items and offer my own take on how to style them successfully, starting with accessories



Why they’re awesome: The cool-tough vibe of a boot without the calf-fitting woes that often accompany knee-high styles.

Why they’re tricky: Since ankle booties end at … well, the ankle, they divide the leg in a way that looks a bit unnatural. Cutting the calf at the ankle can make legs look shorter or “stumpy.”

How to make them work: If you want to wear ankle booties AND make your legs look as long as possible, there are two simple workarounds. Try matching the color of the boot to your tights or leggings, or keeping them in the same tonal range. Obviously, that isn’t going to work in the dead of summer, but it’s a fabulous trick for cooler months and doing so creates an unbroken line right down to the ground. For summertime wear, try to find a bootie in a color that matches your skin tone. If your skin is dark, go with black, chocolate brown, or burgundy. If your skin is light, try for tan, gray, or pastels. Don’t worry about matching your skin exactly, just keep within the appropriate color range and you’ll be fine.

Above you see ankle boots worn with pants, and here the trick is to make sure your ankle itself is showing. On most people, the leg becomes slimmer at the ankle, so a boot that’s cut right at the ankle bone or below paired with cropped or cuffed pants shows that curve.



Why they’re awesome: Cuffs emanate power, and can inject toughness into an outfit without creating imbalance.

Why they’re tricky: A wide bracelet can obscure your entire wrist, making it seem as if your forearm doesn’t taper at all. This can convince the observing eye that your arms are bigger and wider than they truly are.

How to make them work: Since you’re going to be obscuring an area that defines the shape of your arm, balance that obfuscation by showing off other areas. Wear a sleeveless top so your elbows and shoulders are visible. Wear short or fitted sleeves so the overall silhouette of your arm is discernible. Make sure that your OTHER wrist is visible and unencumbered by bracelets.


Why they’re awesome: Obi belts are generally made from soft leather, so they conform to the body more easily and comfortably than stiff leather belts.

Why they’re tricky: Obi belts are generally very wide, so they can visually shorten the torso.

How to make them work: For starters, don’t buy an obi that has a 5″ panel in the front and narrows gradually toward the tie-ends. Unless you’ve got a very long torso and want to shorten it a bit, superwide obis can make you look disproportionate. Seek out a style that is 3″ wide or a bit wider like the Elizabeth Kelly version I’m wearing above. It’s more of a wrap belt than a true obi, but it’s also less likely to make you look like your boobs are perched atop your pelvis.

Now, consider placement. Obis and wrap belts are difficult to wear hip-slung, so you’re likely looking at your wearing waist, natural waist, or right under your bust. If you are interested in making your legs look longer, place the obi high on your torso. If you’re interested in creating an hourglass, place at your natural waist. If you’re interested in elongating your torso or balancing a larger bust, place at your wearing waist. (Wearing waist will likely work best with pants and lower-slung skirts.)



Why they’re awesome: “Statement necklaces” come in nearly infinite varieties, so their awesomeness is somewhat difficult to define. But, in my opinion, statement necklaces are large or long or both, fairly showy, and difficult to ignore. They’re fabulous for dressing up a casual ensemble, can work to balance a large bust or cleavage in some circumstances, and draw the eye up toward your gorgeous visage.

Why they’re tricky: Necklaces that are big all around – like the multi-chain one I’ve got on in the outfit above – can make your neck look short. Necklaces that sit against the collarbone can fight with other accessories. And if you’re already top-heavy in one or more ways, they can serve to enhance that imbalance.

How to make them work: Since the point of a statement necklace is to be eye-catching, allow it to be the focal point of your ensemble. Don’t do a belt, or a wildly-printed top, or a complicated dress in addition to a big chunk of jewelry.

If you opt for a necklace with some 3D heft/bulk, balance it with a scoop, v, or otherwise low neckline. Showing more skin lower on your chest will help make your neck appear longer.

If you worry about appearing top-heavy, longer styles of necklace will help. Opt for a lengthy or layered chain style instead of a collarbone-adorning bib. If you just can’t resist a necklace that sits up on your bust, try bookending your look with some unusual or showy shoes, or creating long body lines with an open-front or waterfall cardigan, monochrome outfit (possibly including hosiery and shoes).

*Which is not the only way! You make your own figure flattery priorities, dangit.

Originally posted 2011-07-29 06:24:12.

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26 Responses to “Styling Tricky Accessories”

  1. coffeeaddict

    This post was so brilliant, I think you should do a series on the topic. I’m so tired of the so called fashion experts telling us what to wear and what not to wear without really giving a reason for it. I love that you took the time and effort to explain the “magic” behind it.
    Here are a couple of more difficult garments: tea length dress/skirt, see through chiffon blouses, over the knee boots, skinny jeans, linen (or other stiff material) tunics.

  2. goldensarah

    hi sally! i would love to see a post about how you keep your closet(s) organized. you have a vast wardrobe (i do, too!) and i wonder how you keep things visible when you are piecing an outfit together – ie how you display your scarves, belts, cardigans, etc. to keep them top-of-mind. i find that when i have my clothes displayed properly i do a much better job not only of WEARING everything i own, but of putting creative combos together. however, my closet is rarely in that kind of state! would love any advice you have!

  3. Beckee

    Thanks for these tips! I have always wanted to try the obi belt, but was intimidated by the thoughts of wearing a belt. You have inspired me with very useful tips about selecting and wearing the obi. I have also feared ankle boots, but now I feel brave enough to tackle them, as well. I have a difficult time selecting skirts for business wear. Please consider tips on how to choose different types of skirts, such as pencil, maxi, full, etc., and what tops, shoes, and accessories look the best with each type of skirt. Sal, you always look fabulous, and you inspire me!

  4. Sarah

    This post was fabulous. It makes a lot of sense now that you SAY that. No one else will give style advice with reason…that I know of. If there are more topics on “tricky styling accessories” I would love to read it.
    (Change of Topic) I will be honest and tell you that I have no read all your posts. I started reading your blog in April. So, I am not sure if you have done this topic…but I would love to see something about accessories (in particular necklaces, bracelets, earrings). I can usually find clothes that I like to wear but when someone says to me, “yeah, you can dress that up or dress it down with some jewelry” I really have no idea where to start, so most of my outfits, go without (I know, thats probably a no-no, but I’m still sorting out the rules of fashion and what looks good on me). It is quite a journey and I really appreciate your posts everyday. They are helpful and inspiring. Thank you!

  5. Cel

    I had to laugh at the one about statement necklaces. I am currently wearing a skirt with a VERY busy print, a brightly coloured tee with a butterfly pattern, and a large, attention grabbing orchid flower necklace… I seem to be going against all the suggestions haha…

  6. Kathryn Fenner

    I just read that Trinny and Susannah say you should match the heft of your accessories–necklaces, heels, etc., to the heft of your bones–you can be small-boned even if you are overweight. This explains why so many larger accessories look off on my, even though I am 5’10” and not slim by any means. I have slim ankles and wrists, so I have a proportionally smaller frame, even though I am larger relative to the world.

    I have trouble with tops to wear with fuller skirts–I have a lovely Eileen Fisher black silk crepe A-line that is incredibly flattering, but I have trouble finding flattering tops to wear with it…

    • pope suburban

      I have that problem too! I love big, bold bracelets, rings, and necklaces, but they rarely fit, and when they do, they have an unfortunate Wilma Flintstone effect. I’ve gotten to the point where I have accepted I will have to make my own jewelry if I want something bold (Try finding a size 4.5/5 ring anywhere, augh), because most of the things I like are on a different scale entirely.

      • Kathryn Fenner

        I think they are saying that bold doesn’t *look* right if you are small boned, even if it ‘fits’– I wear a size 8 ring, and bold stuff still looks “off'” on me. They show necklaces that are bold-ish–a chunkier pendant, but on a thinner cord, say, rather than big beads all the way around.

    • Rachel W.

      Ooh, I second the request for tops to wear with full skirts. I’d love to have more ideas to deploy! The super-casual solid-colored tees I usually opt for work, but it’s a limiting look. I think I’m timid because full skirts (especially those that are patterned or textured!) are so visually interesting that I’m afraid I’ll pick a top that’ll compete with, rather than complement, the craziness of the bottom.

  7. The Redhead

    Well, now I know why my obi belt has never quite worked for me…its tapered!
    Great advice!
    Another way to wear ankle booties without having them visually chop your feet off is to find ones with a dip in the front, or even a “V”. They don’t truly stop at your ankle, but the asymmetry in the front allows a little more skin (or tight) to show and can help elongate the legs.

  8. Stella

    Thanks for this. I completely agree that while well-meaning, most of those fashion rules just turn people off. I have a relatively big butt and hips, so I should try to slim that area. Or at least, that’s what people tell me. But I feel so happy when I wear my bright red pants! So what’s more important? Feeling happy or following the rules?

    As for the ankle boots, I used to dislike them. I just didn’t see anyway they could work, until I tried a pair on. Now, I think they’re just like any regular old pump! I wear them with pants, skirts, walking shorts and a blazer…my pumps are a bit ignored after the inclusion of the ankle boot in my wardrobe!

  9. Patti @ NotDeadYet Style

    Great ideas, thank you. I struggle with statement necklaces. I love them on the rack, but they seem to overwhelm my thin neck. Like you suggested, I do better with the layered chains. Love those ankle booties and the accompanying skirt!!

  10. Nique

    Thanks, Sal. I love this topic because I have all of the “tricky” items you described, and I love ideas on how to employ them better.
    I agree with Coffeaddict about OTK boots. I was a little late to the trend, but now I have two (expensive!!) pairs, and I want to get more use out of them to decrease my cost per wear, especially since the style might not be around for much longer.

  11. Elissa

    Brilliant post, Sal. I especially love your advice regarding ankle boots. I bought a pair back in the fall and have been scratching my head over how to wear them without making my already-short legs look even shorter. I love the idea of pairing them with matching leg wear to elongate my legs. And might I add that the outfit you’re pairing your booties with is seriously divine? Your personal style is truly enviable.

  12. Chelsea S.

    Fabulous post! Honestly I’ve steered clear of ankle booties (other than oxfords) because of worries about not flattering my curvaceous legs, but I think it’s time I took the plunge using your tips!

  13. felicity

    Thanks very much for this – add me to those who are afraid – nay, terrified – of ankle boots. I have shorter legs and strong calves and I admit I fear stumpification. May have to actually, you know, TRY some on at some point!

    I am with Kathryn – I would love some good tips on pairing tops with fuller/gathered skirts. I am larger of boob if that helps.

    Finally, the expression “perched atop” made me smile.

  14. Anne @ The Frump Factor

    Fabulous post, Sally. I’ve come to expect greatness from you, but this one is especially useful and interesting. (Plus, I enjoy anybody who can effectively deploy the phrase “batshit crazy.”) Love that first look with the belted dress!

  15. malevolent andrea

    I would love a post on getting over the psychological hurdles to wearing certain things or certain combinations. For example, I won’t wear booties with a skirt because it feels like bad-80s to me (in the way that wearing huge shoulder pads would, but wearing black leggings and flats or jeans with zippers at the ankle don’t, go figure). Or how I won’t wear my maxi dresses or skirts once it’s not sandal weather anymore, because wearing them with boots automatically feels like Little House on the Prairie to me.

  16. sartoriography

    This is a fabulous post, as always. I agree entirely with how annoying the hard and fast “stylist” rules are, but sure, as a basic starting point they do work. I think you’ve got some great advice here, especially on the ankle bootie (and that outfit is to DIE for!).

    One thing I’d add to the cuff discussion is playing with placement. I’m a huge fan of wearing bracelets and watches higher up on my arm, instead of right at the wrist. It’s a quirk that has turned into a style thing, and I love it (though it baffles the men in my life). 🙂 I’d say that playing around with where things fit you or flatter your particular shape or style really makes sense, regardless of the rule of thumb.

  17. Leah @ Leah Today

    I’m totally with you on this one, despite the forces of the media shoving fashion ‘rules’ down our throats, I’m all for creating my own style, what makes me feel -not just comfortable but- gorgeous also happens to be what works. (:

    Hi, I’m Leah BTW! (:


    I love how happy you look in all your pics!

  18. Tenshi

    Awesome post! I have been contemplating obi belts for a while now and this post just made me realize that I really really need one, pronto. I think I even have a pattern for one somewhere, so I think I’ll make that my next project.

  19. CC

    One quick note on statement necklaces and busty ladies: a chunky necklace that sits just above or even right on the top of the bustline works really well when you have a larger bust. Why? Because smaller necklaces or longer necklaces have a tendency to fall inside the cleavage or get lost in the girls. 🙂
    Thanks for the post!