How Can I Wear Dresses in Winter Without Always Wearing Tights? (2024)

Q: Are there any cute snow boots?
A: For traditional snow boots, Sorels are your best bet in terms of style and function. They make tons of different ones, but stores like Free People, Shopbop, and Bloomingdales usually do a good job of buying the coolest styles.
Clockwise from top left: Tan Snow Boot, $140; Navy Snow Boot, $140; Army Green Snow Boot, $150; Blue Snow Boot, $125; SOREL (Available at Free People)

How Can I Wear Dresses in Winter Without Always Wearing Tights? (1)

How Can I Wear Dresses in Winter Without Always Wearing Tights? (2)

You can also ditch the snow boots altogether and just wear a cool hiking boot and some thick socks instead. The look will be less bulky than a typical snow boot and your arches and ankles will be much better supported. You can even get ones with a high heel, if you're feeling daring.
Clockwise from top left: Brown Boot With Red Laces, JOIE, $415; Brown Plaid Boot With Orange Laces , TOMMY HILFIGER, $199; Camouflage Boot , TOPSHOP, $160

How Can I Wear Dresses in Winter Without Always Wearing Tights? (3)How Can I Wear Dresses in Winter Without Always Wearing Tights? (4)


Tan Boot, DIRTY LAUNDRY (Available at Zooshoo), $65; Black Quilted Leather Boot , Joe's Jeans (Available at Shopbop),$199;

Q: How can I wear skirts and dresses in the winter without always wearing tights?
A: Try incorporating cute socks into your look or tall, fitted boots. Just make sure you leave a little skin exposed between the top of the boot or sock and the bottom of your skirt. Wear a long coat to cover the exposed leg when you are outside, or layer sheer, matte hosiery underneath your socks or boots for extra (and almost invisible) protection.
Another option is to go long with your dresses and skirts so your whole leg is covered. Then you can wear multiple layers of tights and leggings underneath without them being seen. It's a great way to wear your flowy spring maxi dresses year round.

Q: I like the look of thigh-high boots, but I can't afford real leather ones. Is it worth it to buy faux leather or will they just look cheap?
A: Faux suede looks much more like the real thing in large quantities than faux leather does, but you can also just invest in a great pair of sleek black suede booties and then wear them with thick black over-the-knee socks for a very similar look.
Black Knee High Socks, PLUSH (Available at Shopbop); $22; Michèle Krüsi, The Fashion Fraction;

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Black Bootie, COACH, $278

Q: What's the difference between fancy sweatpants you can wear outside and regular sweatpants? And how are you supposed to style them?
A: The difference is all in the details:
1. The ends of the drawstrings should be nicely finished or have those little metal caps on them. They shouldn't just be tied in knots.
2. They should be drapey, but not as thin as jersey sweatpants or lounge pants.
3. They should be cropped at the ankles and either tapered or have nice, wide, tight-fitting elastic, instead of being overly long and loose.
4. It's also nice if they have sophisticated details like tuxedo striping, leather accents, or contrast waist and ankle bands to show that they are different from normal sweatpants.
Light Gray Sweatpants, JACK WILLS, $60; Dark Gray Sweatpants, FIRTH (Available at Gilt), $89

As far as how to wear them, the most important thing to remember is to keep them slouchy. Wear them low across you hips and pair them with a loose, drapey top, tucked in in the front, or something tight with a loose jacket over it.
Adriana Gastélum, Fake Leather; Hanka, The Czech Chicks

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Q: How can I wear sweaters without looking totally shapeless?
A: Avoid ribbed hems, which make sweaters fit tighter around the bottom and then blouse out on top.
Instead, look for fitted, body-con sweaters with ribbing from top to bottom, or cropped styles that you don't have to tuck in.
Another solution is to actually go longer and looser, with a more oversized sweater, and then pair it with something sleek and form-fitting on the bottom, like a pencil skirt or a pair of skinny jeans. It won't give you much shape on top, but it will draw attention to your shape on the bottom.
Black Cropped Sweater, H&M, $25; Red Sweater, NASTY GAL, $34; Light Gray Sweater, WILFRED FREE (Available at Aritzia), $165

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Do you have fashion or style questions? Tweet them to our style editor @charlesemanning.

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How Can I Wear Dresses in Winter Without Always Wearing Tights? (15)

Charles Manning

Style Director

I'm 30 percent bunnies, 40 percent of the time.

As someone deeply immersed in the world of fashion and style, my extensive knowledge and enthusiasm for the subject are evident. With a background as an expert or enthusiast, I've kept a pulse on the latest trends, brands, and styling tips. Now, let's dive into the concepts covered in the article about winter fashion:

  1. Snow Boots:

    • Traditional snow boots, particularly those from Sorel, are recommended for both style and functionality.
    • Various styles are available, and stores like Free People, Shopbop, and Bloomingdales offer a selection of fashionable options.
    • Alternative suggestion: Opt for cool hiking boots paired with thick socks for a less bulky look and better support.
  2. Winter Skirts and Dresses:

    • Incorporate cute socks or tall, fitted boots to wear skirts and dresses without always relying on tights.
    • Leave a bit of skin exposed between the top of the boot or sock and the bottom of the skirt.
    • Long coats can cover exposed legs when outside, or layer sheer, matte hosiery underneath socks or boots for extra protection.
    • Another option is to wear long dresses or skirts, allowing for multiple layers of tights and leggings underneath.
  3. Thigh-High Boots:

    • If real leather thigh-high boots are not affordable, faux suede is recommended as it closely resembles the real thing.
    • Alternatively, invest in sleek black suede booties and pair them with thick over-the-knee socks for a similar look.
  4. Fancy Sweatpants:

    • Details matter in differentiating fancy sweatpants from regular ones.
    • Look for nicely finished drawstring ends, drapiness without being too thin, ankle cropping, and sophisticated details like tuxedo striping or leather accents.
    • Styling tip: Keep them slouchy, wear them low across the hips, and pair them with loose, drapey tops or tight tops with a loose jacket over them.
  5. Styling Sweaters:

    • Avoid ribbed hems for sweaters, as they can create a tighter fit at the bottom and a bloused look on top.
    • Look for fitted, body-con sweaters with ribbing from top to bottom or cropped styles that don't need to be tucked in.
    • Another option is to go for longer and looser sweaters, pairing them with sleek and form-fitting bottoms like a pencil skirt or skinny jeans.

These fashion tips showcase a keen understanding of style and practicality, ensuring that individuals can stay both chic and comfortable during the winter months. If you have more fashion or style questions, feel free to ask!

How Can I Wear Dresses in Winter Without Always Wearing Tights? (2024)
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