In fall and winter, wear Mary Jane flats with warm layers on top and something on your legs: socks, sheer hosiery or opaque tights. Cropped trousers, midi skirts and knit dresses work best, and long coats balance the low profile of a flat. Save them for dry days and indoor wear, and switch to boots when there's rain, slush or snow.
Below: how to layer Mary Janes for cooler weather, tights vs socks, which coats and jackets work, what to wear with black and brown Mary Jane flats, and six outfits built around the Lorissa Orthopedic Mule Flats. For the basics of styling the shoe, see our Mary Jane flats style guide.
Can you wear Mary Jane flats in winter?
Yes, on dry days and indoors, with something on your legs. Mary Janes are a low, open-topped shoe, so they're not a substitute for boots in wet or snowy weather. They're a great choice for the office, dinners, holiday parties, travel days and crisp, dry afternoons.
Be realistic about the shoe you own. Lorissa has a breathable, open-weave leather upper and a backless mule shape. That makes it comfortable through mild fall weather and in heated offices, but it isn't designed for cold rain or snow. On those days, wear boots for the commute and change into your flats when you arrive.
How to wear Mary Jane flats in fall and winter: 5 rules
- Cover the gap. Socks or tights between the shoe and your hem make the outfit look finished and keep you warmer.
- Go heavier on top. A chunky knit, cardigan or long coat balances a slim, low shoe.
- Choose ankle-length or cropped bottoms. Long trousers that drag on wet ground get dirty fast, and a cropped hem keeps the strap visible.
- Swap to darker leather. Black, brown and camel look most at home with fall fabrics like wool, corduroy and velvet. Keep gold and silver for evenings and parties.
- Protect the leather. Keep leather flats away from salt, slush and standing water. If they get wet, let them dry naturally at room temperature, away from a heater.
Tights vs socks with Mary Jane flats
| Opaque tights | Sheer socks or hosiery | Ribbed crew socks | |
|---|---|---|---|
| Warmth | Highest | Light | Medium |
| Look | Sleek and continuous | Polished | Relaxed and cozy |
| Best with | Mini and knee-length dresses, skirts | Trousers, midi skirts, evening outfits | Jeans, corduroy, midi skirts |
| Easiest colors | Black, chocolate, burgundy | Black, nude, gray | Cream, gray, brown |
For a full guide to sock types, lengths and colors, read how to wear Mary Jane flats with socks.
What coats and jackets go with Mary Jane flats?
- Long coats and longline jackets: the most flattering choice. A long vertical line balances a flat shoe and covers most of the outfit, so the shoe becomes the finishing detail.
- Cropped leather or moto jackets: work with midi skirts and dresses. The short jacket shows off the skirt, and the flats keep it casual.
- Knit cardigans and shackets: perfect for early fall, when it's too warm for a coat.
- Puffers: fine for casual days, but pair them with slim trousers or jeans so the outfit doesn't feel bottom-light.
What to wear with black Mary Jane flats
Black Mary Jane flats are the easiest pair for cold months. They work with black, gray, navy, denim, burgundy and jewel tones, and they disappear into black tights for a long, clean line. Pair them with black trousers, a velvet blouse or a knit dress for work and evenings.
What to wear with brown Mary Jane flats
Brown and camel Mary Jane flats suit fall's warm colors: olive, rust, cream, plaid and denim. They look best with corduroy, plaid knits, wool and suede textures. Choose cream or brown socks for a tonal look, or dark jeans for contrast.
Best fabrics to pair with Mary Jane flats in cold weather
Fall and winter outfits look richer when you mix textures. A smooth or woven leather flat sits well next to:
- Knitwear: chunky cable knits, ribbed sweaters and plaid cardigans add warmth and visual weight on top.
- Corduroy: skirts, trousers and blouses in fine or wide-wale corduroy are a natural match for brown and camel flats.
- Velvet: the easiest way to make a flat feel dressy for evenings and holiday events.
- Wool and tweed: tailored trousers and coats in wool look polished with black or brown leather.
- Leather: a leather or leather-look jacket ties in with the shoe without matching exactly.
A simple fall and winter color guide
| Flat color | Fall colors that work | Winter colors that work |
|---|---|---|
| Black | Plaid, olive, rust, denim | Burgundy, charcoal, black, emerald |
| Brown | Camel, cream, olive, coffee | Chocolate, ivory, deep blue |
| Camel | Olive, cream, brown, khaki | Gray, navy, oatmeal |
| Gold and silver | Deep blue, brown, black | Black, burgundy, velvet jewel tones |
6 fall and winter outfits with Mary Jane flats
1. Plaid cardigan and dark jeans
The easiest early-fall outfit. A plaid knit worn open like a light jacket, a plain tee and dark ankle-length jeans. Brown flats pick up the warm tones in the plaid. Shown: Josette Plaid Knit Cardigan in Coffee Brown, Lorissa in Brown.
2. Velvet bow blouse and black trousers
Velvet is a cold-weather fabric that dresses up a flat instantly. Wine red against black is a classic holiday-season combination, good for dinners and office parties. Shown: Antonia Velvet Bow-Neck Blouse in Wine Red, Romilly Wide-Leg Trousers in Black, Lorissa in Black.
3. Corduroy blouse and brown trousers for the office
Fine corduroy, a high funnel collar and brown tailored trousers make a warm, polished work outfit. Camel flats keep the color story soft. Shown: Lorraine Funnel-Collar Corduroy Blouse in Olive, Romilly Wide-Leg Trousers in Brown, Lorissa in Camel.
4. A shift dress with opaque tights
Layering a fine turtleneck under a sleeveless dress turns a summer piece into a winter one. Black tights and black flats create one long, unbroken line. Shown: Amandra Sleeveless Slim Fit Dress in Burgundy, Lorissa in Black.
5. Leather moto jacket and a midi skirt
A cropped jacket over a flowing skirt is a fall favorite. Gold flats with sheer black socks add evening polish. Shown: Coralie Notched-Lapel Moto Jacket in Brown, Eliza Flowing Midi Skirt in Deep Blue, Lorissa in Gold.
6. A long hooded jacket on cold, dry days
A longline jacket covers most of the outfit, and silver flats with gray ribbed socks add a little brightness to a dark winter look. Shown: Cecily Plaid-Lined Hooded Long Jacket in Khaki, Reina Ribbed Knit Sweater in Black, Lorissa in Silver.
When to switch from Mary Janes to boots
Mary Jane flats are a dry-weather shoe. Switch to boots, or carry your flats in a bag and change at your destination, when:
- It's raining, or the sidewalks are wet and slushy.
- Roads and paths have been salted.
- There's snow or ice on the ground.
- You'll be outdoors for hours in freezing temperatures.
For the office, restaurants, travel and dry, crisp days, Mary Janes with socks or tights are a lighter, more comfortable alternative to boots.
Caring for leather flats in cold weather
- Wipe off dirt and salt marks with a soft, slightly damp cloth as soon as you get home.
- Let wet leather dry naturally at room temperature. Direct heat can dry out and crack leather.
- Stuff damp shoes with plain paper to help them keep their shape while they dry.
- Store them somewhere dry and away from radiators between wears.
Find your winter pair: the Lorissa Mule Flats come in black, brown, camel, gold, silver and white. Browse more women's footwear, or shop the knits, jackets and trousers in our women's clothing.
Frequently asked questions
Can you wear Mary Jane flats in winter?
Yes, on dry days and indoors. Add socks or tights, and wear boots for rain, slush or snow.
What do you wear with Mary Jane flats in the fall?
Plaid and chunky knits, corduroy, ankle jeans, midi skirts and cropped jackets, with ribbed or sheer socks.
Do you wear tights or socks with Mary Janes in winter?
Both work. Opaque tights are warmest and best with dresses and skirts. Socks suit trousers and jeans.
What color Mary Jane flats are best for fall?
Black, brown and camel are the easiest fall colors. Gold and silver work for evenings and holiday parties.
What coat goes with Mary Jane flats?
Long coats and longline jackets are the most flattering. Cropped leather jackets work well with midi skirts.
How do I protect leather flats in winter?
Avoid salt, slush and standing water, wipe them clean after wearing, and let them dry naturally away from heaters.