Wearing a tuxedo suit, or “le smoking”, is stunning but probably a little dressy for casual holiday events. One way to get around this is to ease the formality, structure and severity of the tuxedo jacket by combining it with casual elements, like jeans and fluid tops. 

Tuxedo jackets are available in a variety of lengths, colours and fabrics. From Winter white, black and ink blue, to gold, silver, velveteen, sateen, jacquards and patterns. I’ve found that a slightly shorter tuxedo jacket is most versatile because it works just as well with jeans and trousers as it does over skirts and dresses. So unless you are tall, opt for a shorter rather than a longer tuxedo jacket.

Here are the components:

Tuxedo Jacket: I’ve chosen a black tuxedo jacket because it’s the most available colour, but there are many other options too. A satin trim is not essential, as long as the cut resembles a tuxedo jacket. Clean lines, narrow lapels, low stance, tailored fit, and welted pockets.

Relaxed Top: I vote fluid pullover, tee, or blouse in soft fabrications because those details do wonders to relax the stiffness of the jacket. Wearing something stiff and structured under something equally stiff and structured amps up the dressiness factor. Of course, by all means choose a structured top if that’s your cup of tea. These are guidelines and not rules. Keep the top untucked for an extra relaxed effect.

Relaxed bottoms: You’re after casual bottoms, so think jeans, mis-matched tuxedo pants, slouchy trousers, silky track pants, leather track pants, harem pants, leather jeggings, combat pants or a flouncy leather skirt. As soon as you add a pair of tailored bootcut trousers or pencil skirt, you amp up the dressy factor. That’s not wrong, just something to bear in mind since we’re trying to relax the tuxedo jacket.  

Party Footwear: Wear dressy party shoes to complement the dressy jacket and contrast with the casual bottoms. I vote refined, pretty and dressy pointy toed footwear because it’s particularly on trend this season. Leave off the chunky and distressed boots.  

Accessories: It’s a party so a clutch is a must. Structured or unstructured is fine, in either a casual or dressy vibe. I’ve chosen a very dressy and blingy clutch because it’s a fun juxtaposition against casual bottoms. Add jewellery, hosiery, eyewear, and watch as desired. 

Top the entire lot off with a big warm coat, and wear sensible shoes to and from the venue if the weather is bad. Take off the coat and swap out the shoes once you’re back indoors. Most importantly, have a ball!

Casual beanies in all sorts of colours, textures, shapes and patterns are the fashionable hat choice at the moment. It’s fab how the beanie has become quite the trendy item and fashion statement across all age groups for both gals and guys. It’s a practical and fun form of headgear. 

In the same breath I want to remind you that the wool beret is another fun hat option. It’s not the trendy choice, but certainly still a stylish one because it’s a modern classic. And the classics are powerful pieces when incorporated into a modern style. 

When my clients try on newsboys, cloches and beanies in the hat department, I usually sneak in a beret too. And they often purchase the beret along with another hat. The beauty of the beret is that you can shape it into a few different silhouettes, which either expose or cover the ears. It can be dressed up or down, and on the whole is a dressier option than the beanie. So it’s a versatile hat and one that has a high longevity factor. 

I don’t wear hats unless I really have to because short hair, specs, and a small head are not conducive to a successful hat look. To my eye, a larger head, hair that peeks through from under the hat, and no specs work better. That said I do sometimes wear hats to keep warm and prevent earache in the cold. I have a chunky cream wool beanie and a cream beret, both of which I had to purchase in the kids department because like I said, I have a small head.

Over to you. Do you wear berets, or are you devoted to beanies and newsboys?

As I help clients put together holiday outfits this season, I’m reminded that pointy toe pumps and dressy slipper flats can instantly refresh the party dresses and separates already in your wardrobe. Black party wear looks especially fab with dressy metallic footwear, colourful footwear, or black footwear that is colour blocked with another colour. 

Party shoes needn’t be super comfortable because you’re probably seated for most of the time that you’re wearing them. Hence my expression “sitting shoes”. So you might be able to wear a higher heel or a less cushioning and supportive shoe in this case. Adding a cushioning insole is an option for styles that are not cut away in the middle of the foot. 

Here’s a selection of closed toe and heel party footwear, most of which I have seen on clients or tried myself. Comfort levels, colours, heel heights, and price points vary across the styles. 

1. Boutique 9 Mirabelle Pumps: I almost bought these because they look extra sleek and minimal. (Remember how incredible this style of shoe looks in this trouser outfit). They elongate the leg line, and are a perfect shade of champagne. The leather is hard to start off with, but might soften after wearing. Will not work for a wider foot. Might need to size up half a size. 
2. Calvin Klein Baisha Strappy Pumps: I found these much more comfortable than the Boutique 9 Mirabelles because the leather is soft and the toe box roomy. I love the dainty ankle straps, textured leather, and light weight integrity of the shoe. I bought these in gold as my new party shoe. I’ll wear them with black micro fishnets or nude knee-highs in Winter. Great price point. 
3. J.Renee Aziza Strappy Pumps: These are fairly comfortable, and the tortoise shell option is unique. The ankle straps are a little short so consider yourself warned. 
4. J.Renee Staci T-Strap Pumps: A little retro and very pretty. Read the rave reviews. 
5. J. Renee Tomlin Flats: Studded heels are a subtle way to wear foot bling. Low heeled, snip toed, and works for a wider foot. Goes up to a size 13. 
6. Kenneth Cole New York Mirror Me: A lower heel with a cushioning footbed. Pretty comfy and basic. Will not work for a wider foot. The silver option looked better to my eye because the gold version is overly brown. 
7. B Brian Atwood Macias: Stunningly elegant on the foot. Runs small and narrow so size up half a size. Also available in shocking pink. 
8. Tory Burch Carissa Bow Smoking Slippers: Textured black, bling bow, and pretty comfortable. Better with the addition of an extra insole. 
9. RED Valentino Flat Loafers: More textured black in a romantic floral. Add an insole. 
10. Coach Camille Pump: A d’Orsay style in ruby red. Also available in black and taupe. Read the rave reviews. 
11. Vince Camuto Ecie Flat: Almost as comfy as a real slipper. Cushioning and adorable in all colour options. 
12. Joan & David Mitzie Flat: Sleek, fashionable, comfy and on sale. Gorgeous gold heel. 
13. Matiko Dot Flat: A little more casual than the Mitzie, not quite as comfy, but the black and gold option is very fun.  
14. Vince Claire Pump: On trend, soft leather, comfy and elegant. The high vamp of this d’Orsay style adds a little edge. 
15. Vince Aurelian Pump: Here’s the low-heeled version of the Claire. 
16. Kate Spade Adie Pump: The leather is hard and will not stretch. Gel inserts help create a more comfortable fit as does wearing hosiery. Eye-catching and modern classic. All three colour options are gorgeous and on sale. 
17. Nina Lars Bootie: A refined and sparkly bootie that’s great for evening wear. The fabric upper is pretty hard so it’s not a comfy option. But fine for those with less fussy feet. 
18. Nina Originals Pledge Slipper Flat: Soft, comfy and cute. Fun colours and one option for Team Flats. 
19. Steven Thriisha Bootie: A cut-out bootie for Team Extra High Heels.  
20. Jimmy Choo Bow Pump: Ladylike and especially sublime in the blue. Modern classic, high longevity factor, and runs small. 

Extra Tips: 

• Add hosiery to party shoes for warmth. Think sheer black or dark grey hose, black textured hose, black micro fishnets or nude hose when wearing a dress or skirts. Think sheer knee-highs in black or nude with trousers and jeans. 
• Stretch shoes with wet feet if they’re a tad snug all round. 
• Complement party shoes with a clutch. 
• Swap out weatherproof footwear for party shoes when you’re back indoors after a challenging commute.
• Wear party shoes with jeans as well as dressy attire. 

I’ve focused on pointy toe footwear because the silhouette is especially on trend at the moment. Fresh and fashionable. But if round toed dressy shoes are more your thing, by all means wear those instead. Round toes tend to be more comfortable and are not dated.

This is what I’ll be wearing next week on Thanksgiving Day, after I’ve finished cooking for the potluck we’re having at dear friend Meredith’s house. It’s comfortable, warm, casual yet a little dressy, and most importantly – roomy. I know better than to wear a body con sheath dress on a day that is about eating lots of food and relaxing with friends. 

The cream cable knit sweater is the only new item in the outfit. Greg bought it for me four months ago for my birthday just as the new Fall collections were hitting stores. He loves it when I wear cuddly knitwear, and I love that Greg has impeccable taste and found this piece for me. I instantly adored it and rejoiced in the fact that it’s not scratchy and that the sleeves had length. This cabled darling hits all my buttons. It’s chunky, yet not overwhelming because of its cropped length. I love the colour and the bulky weight. I love the leather trim on the neck, shoulder and sleeve hems best of all, which is what distinguishes it from the other two cream cable knit pullovers in my closet. 

I haven’t been able to wear the new sweater till recently because I had to wait for cold weather. It was hard to see it hanging in my closet for so long because I bat for Team Wear. But now with Winter in full swing I know I’m going to make up for lost time.

Black bottoms are an obvious pairing because they match the black trim on the sweater. I chose my favorite black bottoms for the pullover’s debut: The Alice & Olivia boot cut pants with wide waistband. They are dressier than jeans, with lots of drape and also a little volume. The volume is important to offset the cropped integrity of the sweater, which is why I did not choose slim fit pants. Later I noticed that the leather trim of the pullover matches the leather trim on the trousers. A tiny nod to the matchy-matchy trend. 

I wanted the welt of the cropped sweater to rest on the waistband of the trousers. I wore a patterned Burberry belt because I prefer to fill exposed belt loops. The visual effect is a subtle form of “volume on volume”, which is not everyone’s cup of tea. Tucking a tailored turtleneck into flared trousers is more conventionally flattering, and I certainly wear that combination too. But this combination is more interesting, is on trend and looks fresh to my eye. It’s fun to forgo a little conventional flattery for the sake of fashion, and there is still ample structure in the outfit to suit my style preferences.

I finished off the outfit with a seven year old pair of pointy toe moto shooties that are so beaten up that I have to fill in their bald patches with a black Sharpie pen. But they are super comfy and my favourite hard-to-find low heel height, so I’ll keep them until they are completely unwearable. Specs, watch, wedding ring and small black clutch are all I need in the accessory department.

My old cream double breasted wool coat goes over the entire lot, which I wear both open and closed. The outfit is voluminous when the coat hangs open, and more structured when the coat is buttoned up. I like both versions. 

The sweater looks great with a skirt, but trousers are so much warmer. For that reason I have become a trouser gal. I do go through phases of missing my skirts, but they just don’t offer the same insulation. I’m wearing pantyhose under these trousers for extra warmth and will swap out the hose for thermal leggings when temperatures drop even further. I’ll need to live in a warmer climate if I want to wear skirts and dresses more regularly. It’s taken me years to understand this about my style needs, and finally the penny has dropped. I live in Seattle and I bat for Team Trousers.