I’ve had a number of requests around this topic lately and after many failed attempts to wear dresses and not freeze, I think I’ve cracked the winter dress wearing code. We might assume that it’s about choosing a really warm dress, and while that’s not a bad plan, I’ve found it’s actually more about what goes under and on top that makes the most difference.

So today I’ll be running through a few of my best tips for winter dress styling to help you keep your favourites frocks out of hibernation!

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SHOP THE LOOK: EARMUFFS | COAT old Elizabeth Suzann | BAG old Opelle (this one is so cute)| SLIP DRESS gifted, colour sold out | TUNIC SWEATER old Eileen Fisher (similar here and here) | LEATHER GLOVES | BLACK LEATHER KNEE HIGH BOOTS (very similar to the pair I have)

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TIP ONE: BASE YOURSELF WITH A FITTED TEE & TIGHTS

This is my first step when it comes to dressing for any cold day generally and dresses are even easier to layer underneath.

I start with either a pair of OPAQUE TIGHTS (my favourites) or a pair of BLACK LEGGINGS (shown below) with BLACK SOCKS. While I like the look of a sheer tight, they are basically one thread away from bare legs, so I tend to avoid them (although these are intriguing).

Then I pick a FITTED TEE, SCOOP NECK (shown below) or TANK that won’t show under the dress I’ll be wearing.

For instance above, I’m wearing a pair of leggings and socks (I go for black on black to create the illusion of seamless tights) with a scoop neck, 1/2 sleeve tee that will add insulation without showing above the neckline or sleeves of my dress.

SHOP THE LOOK: Scoop Neck Tee | Perform Leggings (both are true to size) | Luggage Tag Necklace

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TIP TWO: GO FOR A DRESS WITH LONG SLEEVES

A dress with long sleeves feels more appropriate for winter and having some fabric to keep the cold off the skin always helps.

If you need an extra bit of warmth but don’t want to deal with layering more sleeves, I love a sweater vest (like this one or this one) over a dress.

SHOP THE LOOK: FAYE DRESS (more detail here)

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TIP THREE: LAYER ON A LONG TAILORED COAT

I understand the urge to reach for a puffer coat when it’s cold out but if you can help it, a long tailored coat will maintain a more sophisticated and elevated feel to the look. It need not be floor grazing, but I tend to prefer options that hit just above the knee or below.

Elements that make a tailored coat more comfortable to wear over a dress are:

• Inner lining that is smooth (such as silk) and doesn’t make the base garments bunch up.
• A deep back vent so that longer layers don’t get tangled up around your legs or constrict movement.
• A slightly oversize fit will actually keep you warmer than a snug fit because it allows for air flow and insulation from the outside cold.

SHOP THE LOOK: EARMUFFS | CASHMERE SCARF | BAG old Opelle (this one is so cute) | FAYE DRESS (more detail here) | London Coat (plaid option sold out) | Luggage Tag Necklace | REKNIT GLOVE BOOT | GLOVES

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TIP FOUR: STRATEGIC ACCESSORIES

I swear by these three winter accessories:

COZY EARMUFFS

I typically go for earmuffs over a hat or headband because they keep my ears warm without interfering with my hair or creating the dreaded hat-head.

CASHMERE LINED LEATHER GLOVES

I have my Mum to thank for these and they really do make all the difference. My hands stay cozy and the gloves are streamlined enough to still slip into my purse or pockets when I’m ready to take them off.

LIGHT CASHMERE SCARF

I wear this ivory cashmere scarf all the time in the winter and it’s my #1 choice for dressy occasions. I like to add a light element to soften the palette of my outerwear. I also find a lighter tone hides lint and flecks of fluff better than darker colours of cashmere so it’s always ready-to-go.

SHOP THE LOOK: COZY EARMUFFS | CASHMERE LINED LEATHER GLOVES | LIGHT CASHMERE SCARF | LONDON COAT

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TIP FIVE: CHOOSE BOOTS ACCORDINGLY

FOR A LONG DRESS/SKIRT: I tend to find that a TALL GLOVE BOOT with a streamlined fit is the most versatile for styling across the board and I love how they look with a long dress especially.

FOR A SHORT DRESS OR SLIP DRESS: BLACK LEATHER KNEE HIGH BOOTS are my top pick. I find this protects the lower leg from the cold and it visually balances a shorter dress or a slinky slip dress.

SHOP THE LOOK: FAYE DRESS (more detail here) | Luggage Tag Necklace | REKNIT GLOVE BOOT

SHOP THE LOOK HERE

SHOP THE LOOK: EARMUFFS | COAT old Elizabeth Suzann | BAG old Opelle (this one is so cute)| SLIP DRESS gifted, colour sold out | TUNIC SWEATER old Eileen Fisher (similar here and here) | LEATHER GLOVES | BLACK LEATHER KNEE HIGH BOOTS (very similar to the pair I have)

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TIP SIX: SKIP THE CLUTCH & OPT FOR A CROSSBODY BAG

I realize cross body bags aren’t everyone’s top choice but they tend to be mine.

I like them in the winter for a few reasons:

• They keep your hands free, to hold a warm drink or tuck into pockets.
• They can help keep your coat from blowing open if you have a closure-less outer layer.
• They’re harder to leave behind when they’re attached to you! Especially if you’ll be in and out of an uber or on transit.

I think a bag that’s black leather with gold hardware feels fancy and festive but still versatile enough to work with any coat and suitable for a wide array of occasions. I designed mine in collaboration with Opelle years ago but they still have several options in a similar vein.

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TIP SEVEN: LAYER MONOCHROMATICALLY

If you want to extend the use of your lighter dresses, like a silk slip, I recommend layering a knit of the same hue over top. This adds dimension and texture to the look without chopping up the palette.

SHOP THE LOOK: SLIP DRESS gifted, colour sold out | TUNIC SWEATER old Eileen Fisher (similar here and here) | BLACK LEATHER KNEE HIGH BOOTS (very similar to the pair I have)

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& THOSE ARE MY TIPS FOR STAYING COZY IN YOUR DRESSES THIS WINTER!

Thanks for tuning in! Let me know if you’ve got any other techniques to keep your dress collection out of hibernation this season.

NEED MORE LAYERING HELP? CHECK OUT MY WINTER LAYERING 101 POST.