Monday, 07 January 2019
The Dressing Well Blog
Kathy Smith

5 Ways to Wear Short Pants in Cold Weather

By Dressing Well Stylist Kathy Smith

Not too long ago, short pants were a seasonal wardrobe choice worn mostly in warm weather. Today, they are literally "cropping" up in all seasons giving the trend a much wider range of style interpretations for both men and women. They can be preppy and very casual when worn with sneakers and other flat footwear and quite fashion-forward and sophisticated when dressed up with heels and a variety of hosiery.

Below we share five short pant insights that will help you wear them well this season (and beyond!):

#1 Get Your Prep On
Men and women can connect with their inner preppy by sporting “highwaters” (many achieve this look by rolling a pair of jeans of khakis at the hem) and slipping on a pair of simple sneakers or loafers. If you choose to wear socks (some do, some don’t, even in winter), stick with white athletic ones to keep your prep high. Same for sneakers – white works best here too. Can’t believe this look is popular again? Visit any college campus to see how fast this re-trend has taken off!

#2 Split for Comfort & Elegance
Culottes and Gauchos refer to skirts in varying lengths that are divided into two sections to cover both legs. They have stood the test of time (they were introduced in the 19th century for cycling) and today, the most stylish ones worn in winter are high waisted and land anywhere from just below the knee to mid-calf. Tall and short boots are an easy way to wear this trend in cool weather. We love them with tops tucked in and cropped jackets and sweaters when you want a layered look.

#3 Balance Hems, Patterns & Fabrics
Let’s face it: choosing the right footwear with shorter style pants can be daunting and keeps a lot of women away from an otherwise sensible trend. Pants with a strong pattern or cuff as well as those made of heavier fabrics are typically supported well with boots, shoes and sneakers with strong heels and soles. Those that are made with lighter-weight fabrics tend to appear more fluid and skirt-like and can be easier to coordinate with more delicate and lightweight footwear, including those with slimmer heels and open-toes, even in cool weather.

#4 Show Off Your Socks (Or Some Skin!)
Socks are certainly having a fashion moment and shorter pants show them well. Women, bring your style to new heights by showcasing ankle socks with your shorter winter pants. They can be worn on their own with pumps or flats or layered over tights. If your internal thermostat is ok with it, bearing some skin between the end of your pant and where your footwear begins is on-trend too. An ankle pant and a midi boot lets your winter skin shine in the “warmest” of ways! Men, in most professional settings pants that are hemmed properly will allow you to show off your socks appropriately – aka when seated! If you walk into a meeting and everyone is trying to read your socks, your pants are probably too short for the business of the day!

#5 A Word on Traditional Pants
If the pants in your closet are feeling dumpy, chances are they are too baggy and/or too long. In general, traditional pant silhouettes for both men and women are slimmer these days. With their trimmer fit, you want to be sure they are hemmed properly. Generally, that means right at the ankle for women (with no noticeable break) and at the ankle with a slight to no break for men. You want to avoid pooling at the hem at all costs. Our female clients love having a few pair of perfect-fitting slim ankle pants that can be worn with both flats and heels. We source them for all sizes and shapes from designer to discount brands. For the men we work with, we often take good-quality, flat-front pants that they have owned for a while and have them slimmed down on each side and shortened by a skilled tailor. Violà – new pant, new, more modern man!

Editor’s Note: If you’d like some additional assistance figuring out how to wear short pants well this winter, we are here to help. With the trend continuing into the spring, it’s a good investment to understand how to do it well. Our virtual styling program can be fast (order a Fast Fashion Advice session for just $30) or more in-depth (our Signature Virtual Consulting Program is available too). All you need is a computer and a camera. Private one-on-one sessions offer the most customized approach and can be conducted with you in your home or at a local store. Let us know if we can be of help with any of your fashion challenges. We welcome your short pant stories below in our comments section too – everyone has one!

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Kathy Smith

For Kathy Smith, clothing and fashion are an extension of who she is. Raised by a mom who was a professional model, Kathy had a bird’s eye view into styling at an early age as she accompanied her mom on photo shoots and watched as a styling team pulled together an eclectic array of clothing and accessories for her mom to bring to life. She recalls being stimulated by the colors, shapes and silhouettes of the selected fashions and speaks fondly of the impact this experience had on her career path.

Learn more about Kathy »

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IIFD 2019-01-08 06:30

These are great solutions to deal with cold in winter and save yourself from bad impacts of cold on your health. Women can use these type of pants as per their interest.

Kathy Smith 2019-01-09 10:43

Thank you for your note. Having options of what type of pants to wear (and how to wear them) in the winter is a good way to shake up the long winter days. The great thing about these options is that they look good on just about everyone!


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