Winter Style Tips

Today I received another cry for help. I was asked to settle an age-old style dilemma for a client who is headed to the races this weekend. She and her colleagues had differing opinions on the subject of stockings & sandals, so I was brought in to settle the argument.  I thought I’d share this letter with you all because as the colder weather sets in, it just may help many others with similar questions!

“Dear Al – I need your expert advice …

There are a few of us off to a marquee at the races this weekend. We are debating whether or not sheer stockings can be worn with peep toe shoes / ankle boots. Personally I’m not a fan, but then have seen some celeb shots in mags where stockings have been worn with SANDALS!! What is your honest opinion? I need to settle this argument!”

This is probably one of THE biggest reasons I hate winter! Those “Dress code do’s & don’t difficulties” combined with the leg and foot-covering dilemmas! In summer, it’s easy – a touch of Dove Summer Glow and off you go! But what do you do when it’s freezing and you need to get all dolled up? Arrgh!

Personally, I’m a closed-in shoe with all stockings girl. And bare legs only with sandals/sling-backs. In general, nothing in between will work for me. If it were a dressy occasion in cold weather I’d only do a closed-in pointed-toe with sheer stockings. With opaques I prefer a closed-in stacked heel with a slightly rounder toe;  I’d save super-sheer stockings with a slight sheen for stilettos with cockroach-killer toes!

BUT nowadays (yes, I know I sound old!) and mainly because it’s becoming so much more acceptable in the modern fashion world, I think it can be done but only do it if you absolutely must AND pay attention to my Stocking/Sandal Rules below – for whatever they’re worth:








  • Only wear opaques with peep toe shoes and always peeps with a closed-in heel – regardless of what you see on Runway models or in fashion mags.And never with a sling-back or fine strappy shoe.
  • Choose highest denier stockings/opaques (i.e. 80 plus), not low-denier opaques with reinforced toes – you really can notice the denier difference
  • Never wear open-toed strappy sandals with sheer stockings
  • Avoid brightly painted toenails to keep the attention away from the toes, just in case you can see the nails through the stockings!

Other tips/exceptions for Winter

For those who refuse to take the above advice, please at least take note of the following basics:

  1. NO stockings (sheer or opaque!) ever with fine-strappy/evening sandals or flat sandals (no matter what colour!)
  2. If you are going to do opaques with sandals make sure they are at least a) Chunky (both the straps and the soles/heels) and, b) Both stockings and shoes are black.
  3. Fishnets are easier to relax this rule with, as really, they are 50% leg and 50% stocking so it’s generally 50% easier to work around them!
  4. Make sure when wearing opaques you also match your fabrics to the season – i.e. try to make your dress slightly less summery.
  5. In winter, go for slightly heavier fabrics, or even just a slightly darker shade at the hemline if possible, to avoid a stark/heavy contrast of colours.
  6. Avoid snow-white in a sheer fabrics at the hem, if wearing opaques – opt for cream/winter white if possible, and finally…
  7. In winter, at least cover up on top with a little cropped jacket or something else warm to bring “winter” into the rest of your outfit

Now – rules aside. I just thought I’d share with you some little known facts and a few personal opinions of my own…

European men view the arch of a woman’s foot (and even “toe cleavage”)  as the sexiest part of a woman (other than the obvious others). For this reason, I always advise my clients when choosing footwear/leg-wear (in both winter and summer) to heed the following:

Choose a ballet flat that is cut LOW on the arch of the foot – high-cut ballets, though you  may find them practical with your orthotics – are NOT sexy.

Look for toe-cleavage – again, it’s sexy, not frumpy. We don’t want “kumfs” we want style and comfort. Sometimes the two ARE mutually exclusive!

Seasonal Affective Disorder (or S.A.D Disease) “sadly” applied to fashion!

  • If it’s cold enough to cover up, up top, it’s cold enough to cover (at the very least) your toes! Therefore…
  • NO thongs in winter and equally, please, no sandals either!
  • Footless tights are a good compromise (yes, even if you wore them in the 80’s!). They’ve actually slowly morphed into a fashion trend/classic now, believe it or not! I’d much prefer to see a woman in a dress/skirt (at the appropriate length for her age/personality) with footless opaques and a stylish ballet flat or heel (see above) than to see a woman hell-bent on “never wearing leggings) going bare-legged in winter (or worse – wearing stockings and sandals!

There are so many things to consider when it comes to styling (that’s why you ask me, isn’t it?).  Be it questions about the right length of pants/jeans, the length or cut of stockings (i.e full, footless, cropped, stirrup), the colour of shoes vs tights, skirts, the length of skirt/dress to tights and height of heels, to fabrics etc. The list goes on….

Still confused? Please don’t be shy…ASK AL! If you have a different opinion, again, don’t be shy; I’d love to hear your views! Just remember, opinions really ARE like bums…everyone has one – and these are just mine! 🙂

6 Responses to Winter Style Tips

  1. I feel the cold terribly so I have been wearing black opaque tights with a black low heeled court shoe, I cannot wear high heels.
    I recall seeing a women wearing a lightweight white floaty suit,
    knitted white tights and black court shoes.
    Hope you didnt hit your head as you fainted.
    I had to speak up, I kind of knew her.
    I told her what my mother told me,
    stocking/tights and shoes should not be darker then the hemline.
    Though she slways maintaned white stockings and shoes were right for a navy
    dress with a sailor collar.

  2. I did almost faint – many thanks for the warning! I guess it’s never quite so “black and white” (pardon the pun there!). Our mum’s did actually know what they were talking about too!

    I believe you’ve got to consider fabric, colour, shoe style etc. Tights/shoes can be darker than the hemline these days (think charcoal/grey etc) – for me, it’s more about the stark contrast between “seasons”. Otherwise we’d all be a sea of black in winter (which many of us are, I guess). I like to balance this darkness with something to lighten up on top though. I like tonal variations; shades of a theme and remaining in keeping with the season in terms of weight of fabrics, layering and looking appropriate for occasion, location and climate. I know you get it xx

  3. Hi Alison,

    Thanks for the great post! I agree whole heartedly with everything you’ve mentioned. I do however, have somewhat of a different winter style dilemma of my own and would love your opinion on it.

    I love to wear ballet flats (I prefer the low-cut ones myself, so if I’m ever in Europe, hopefully I’ll be set!) and ballet flats and jeans are my staple! But as it’s getting colder, I find myself wanting to wear something warmer on my feet but have no idea where to go from here.

    I’m 22 years old and I’m a size 6-8 pear shape so prefer to wear straight-ish jeans and lots of layers up top to balance my shape, but find that my legs are too short to wear boots over the top of my jeans which seems to be the trend for winter and am afraid I’ll just end up looking short and frumpy….or a pirate….Do you have any advice?

  4. Hi K-Maree

    Oh I DO understand your dilemma! In fact I share it!

    Ballets and skinny jeans, layering on top etc are my fail-safes too BUT in the cold weather, ballets are not quite warm enough. It’s a tough one (more for you than me ‘cos I’m an old-bag and we old girls can get away with slightly more conservative options)! That said though, luckily this season the classic loafer (or driving shoe) is very much in; and moccasin styles if you like? Both of those have just that little bit more cover on the foot, and really do make a difference when it comes to heating up the tootsies!

    If you don’t like those, there’s always ankle/calf-length boots? I do wear boots over very skinny jeans/jeggings but I struggle to find ones that aren’t too long and make me look like “Puss ‘n Boots”. If you can find ones that you can cuff/fold down slightly lower to shorten them, that will also add length to your legs. That’s the key to not getting lost in them! And watch out (again) for too stark a contrast of colours. If you can find a nice tan or taupe/grey boot, you’d balance out the top half more than relying on basic black boots with everything. Mind you, black boots are classic; would also be a fail-safe with black jeans/jeggings and certainly wouldn’t cut you off. Just don’t do a puffy-sleeved white shirt on top and you’ll never look like a Pirate, I promise! Al xx

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