What to Wear to an Evening Winter Wedding

What to Wear to an Evening Winter Wedding

Oct 25, 2023


Lovely winter wedding dress from bhldn.


If you are anything like me, then that invitation to a rare event, like a wedding, can really throw you, as far as the outfit goes. It can be really awkward getting dressed for an event outside our normal range of activities. Often we just don’t have the clothes for it, particularly if there is quite a formal dress code. As an example of this kind of situation and my decision making process, I am going to tell you about a wedding I was invited to a couple of years ago, in the early days of my image consulting. It is partly interesting because either I now know myself better, or my preferences have changed since then and I would probably handle this differently. But this is how I did it back in 2014.


The event was a winter wedding and the stated dress code was formal, but it was not as straight forward as wearing a lovely velvet gown and heels! There were a number of factors that were at play. Firstly; ones relating specifically to me and my life, secondly wider factors such as weather and thirdly the dress code!


The factors in my life that I had to consider: As a stay at home mother I had not been buying much business or cocktail wear that could be gussied up, and no formal wear. My social calendar included mum type events such as trips to the park, shopping, visiting friends and family. My dressiest events include an occasional dinner out with friends where jeans were the norm and church on Sundays to which I usually wear some kind of pretty day wear, which could have been ok for the wedding, but I was a bit unsure.


And I remember that budget was an issue. I had planned ahead what I would need for the year and then got organised and bought it. I had no real budget left, and so I did not want to buy a big dress, I thought maybe I would stretch to a cool separate that I could wear again in different ways. As far as setting a budget for clothes, Pete the Planner (a wise financial planner that you can find at www.petetheplanner.com) recommends spending between 2-5% of your income on your appearance. That is for the whole family and includes haircuts etc. Depending what you earn that could be a little or a lot. You may not stick to that, but if you go over, be aware that that money is being taken from another category - holidays perhaps, or the family’s fun kitty, and you may not want to do that.


If I had been going to an awards night where I was guest of honor, no doubt I would have broken my budget, but not just for a wedding!


In addition, my outfit choice was profoundly affected by the fact that there was going to be dancing at this wedding. Dancing! Now, I love to dance. Before we had kids we used to go dancing for fun. When I heard that there was going to be DANCING that ruled out a lot of my shoes.


Luckily I had the perfect pair. Black, 1 1/2 inch block heel with a lovely cross over vamp and adjustable ankle strap. They are vintage 90s sportsgirl and they stay on the foot when dancing. They are not too high, and at the time of this wedding, they had half their sole worn smooth, so they had just the right amount of spin for dancing. If you are anything like me you know what you can get away with in a shoe, for me, anything that is held firmly onto the foot is pretty comfortable. These shoes are not too high, but I can even wear a high heel if it has a high vamp, like a peep toe bootie or an ankle strap. What I often struggle with is a shoe that does not hold me around the heel lets me slide down into the toe box and it is uncomfortable. I have a foot narrow near the ankle and wide at the toes. So I cannot say enough in praise of ankle strap shoes. As you can see from my banner above, they are one of my favourite things! Those blue ankle strap pointy toe shoes were not in my wardrobe at the time of this wedding, but they are my most favourite heels EVER. If I had to choose one shoe (heeled) to rule them all it would be those. But, these then were the shoes that I knew I had to wear to the wedding if I wanted to dance the night away (in shoes).


But what to wear on the rest of me? Let us introduce the general circumstances attendant on this wedding (ie things that affected more people than me; the weather and the dress code).


Dress code: Although the organiser specified formal on the invites, it was not that simple.


The couple were being married in England, and just coming out here for a honeymoon, so it was not the real wedding.


A variety of people of all different ages, including children would be at the event. Not just one social group, but a whole church congregation. Although the venue would be somewhat dressed up, under the tulle and balloons it was still the “cultural hall”of our chapel (basketball marking on the floor etc).


And I knew that there were going to be some blokes who were fairly casual - chinos and shirt if not jeans and t. So really it was a very open dress code, you could be totally dressed up or dressed down. I felt like hiding in the middle of the pack, not the most dresssed up but not in jeans either.


The weather was another important factor - it was going to be cold on the way there, although the hall should be fairly heated it was not summer maxi dress weather. Which was a pity. A good maxi dress is the perfect bridge from casual to formal.


One last impacting factor that I forgot to mention earlier, although it is a very personal one and not general at all was the fact that earlier formal wear that I had bought, pre children, was just that, PRE CHILDREN. It was in great condition. I however had a mummy tummy that I did not want to put on show. I used to be pear shaped, but at the time of this wedding I was a fruit salad, an apple on top of a pear. So that meant some stuff did not fit and some stuff looked pretty bad.


And the other personal factor, that I had forgotten to mention was that I did not want to wear black. As far as colouring goes, I am a light spring, light springs don't look fab in black, at least not without a lot of make up, and a lot of cheap easy formal buys are black. If you are clever you might have noticed that my profile photo is of me wearing a black top (actually a dress, but you can't see the skirt). That is in part because I do look good in that photo, and I was proud of the fact that I do such good make up that I, a light spring, could wear that dress and look great. So there. But I was not wearing black to this wedding. I had decided. Silly perhaps but you are what you are! So, these were the items I had already that I decided against


  1. The red satin bridesmaids dress from my sisters wedding. Fit – good. Hides my spare tyre and looked really good actually. Good with the black mid heel block sandals that I wanted to wear). Colour – this was the killer. I had it made back in the day before I had my colours analysed. I used to love this dark red, but it just doesn’t suit me that well.


  2. Blue full length gown. Colour – good. Is roughly on my palette. But somehow, I felt it was Too Much Dress (TMD). I am not liking fit and flare much at the moment. I considered tying a shirt over the top and it was some what better!

    Then I saw this picture on Jean's blog and thought - YES! I wanted a knee length tulle skirt and denim shirt.


    Don't they look chic? I particularly liked the one on the right with the denim shirt knotted over the top. Classy, dressy, yet not over the top. AND fun! But I couldn't dance in those shoes!


    I got the denim shirt from rivers for $20, and the tulle skirt, seeing as I did not want to sell a kidney, I got it from ebay. Hmm. It arrived with an ankle length tulle overskirt and a knee length underskirt that was uneven and it looked what it was - cheap. I sighed and moved on. I have only just now, five years later, managed to live out this sartorial dream - I have a lovely red tulle skirt that I picked up at Princess Highway. I love it with a soft jumper and boots or drapey button down shirt. Yum.


    So what did I do? I fell back upon my little brown dress (a lovely dress in rose brown that is a light spring equivalent of the little black dress.)
    I bought it eleven years ago. I spent a whole day on bridge rd in Richmond looking for an outfit for a wedding, and found this. I love it, both colour and style. It was a little thin for winter, but I paired it with my dark denim jacket. This helped hide my fuller figure and provided warmth as well as dressing the dress down a little. Perfect. I had my grey woolen dress length coat for if I was freezing. Not a true light spring colour, but better than black! I added skin coloured tights, big earings and my dancing shoes. I felt great in it and was on the spectrum of casual to formal, but towards the dressier end – which was where I wanted to be! Just goes to show that spending the time to buy good quality items that we love is worth it. I have worn this dress to three weddings now, over the course of 15 years, as well as some less formal events. It is truly versatile. I would happily wear it to another 5 evening weddings. It just works for me.


    Since this event I have added a few other items to my wardrobe that could have filled the gap. I was eyeing off this dress at anthropologie for ages, and found a similar pink one instead!

    Absolutely stunning, i wanted it in Ivory. Byron Lars at Anthropologie carissima sheath dress. Repeat style.

    The dress I actually bought and now have in my cupboard for future weddings and other such events! On me it is a nice midi length.


    And the take away from all of this? If you get an invite to an event look at your own factors (what you already have, budget, preferences) and then external factors such as dress code, weather and location (don't wear stilettos to a garden wedding or you might get stuck in the lawn etc) and decide what you feel comfortable doing. Sometimes the dress code has greater lee way than at other times. And pay attention to what you like and, perhaps and keep a couple of items on hand. Only if your weight doesn't fluctuate too much and you can foresee wearing them in the next while. It is a waste of money to shop for the life that you don't have. For example I have some silk shirts, an ivory blazer and black evening pants that will take me to many places, as well as the lb(rown)d and now my pink lacey. And shoes to go with all outfits. So, I don't panic too often any more. As you will see my evening basics are very classic and in neutrals from my palette - ivory jacket is my light neutral, rose brown is neutral, pink is off my palette and I find pink easy to pair with other colours from my palette, and the black pants are neutral and far enough from my face that it doesn't matter that they are not on my palette. And they go with the ivory jacket. So for yourself, if you are going to buy a couple of items to have on hand in case, either find a dress in a colour you love (dresses can stand alone so their colour can be bolder) or pants in your dark neutral and a faux twinset in your light neutral, great shoes and fab make up and you are done! (Faux twinset is either jacket or cardigan, depending what you find easier to fit and a blouse or shirt, all in roughly the same colour but not necessarily the same fabric - eg lacey blouse with blazer, both in ivory.) Both lacey blouse and jacket can be remixed with things of another colour, worn with jeans for a more casual dressy look and perhaps to work, depending upon cut, diaphanousness of said blouse, and work dress code. Pants can be like wise remixed and I will be pairing my dress with a denim jacket and white blazer for some other date night looks. I am going to stop now, before I launch into what makes a good evening pant, whether or not evening shoes should be black or nude for you, and what necklaces are trending for evening wear. Otherwise we will be here all year!!