Your “Classic” Winter Wardrobe Checklist

I am a huge fan of building a classic winter wardrobe.  While I do have sections of my closet that are one-off items that are more colorful, festive or specifically for an occasion, I gravitate towards classic, neutral clothing that can easily transition throughout the year for the most part. 

Building a classic winter wardrobe is all about quality over quantity, ensuring that every piece serves a purpose and seamlessly blends with the rest. If you love a timeless, transitional look, this checklist is your guide to curating a classic winter wardrobe that’s both sophisticated and practical. Let’s get started!

My Winter Wardrobe Checklist

The Outerwear

I tend to splurge in this area for two reasons:  if you stick to classic cuts, your investment will stay in style for years, making the cost per wear much less than buying a trendy jacket or coat that you have for a shorter period of time.  And, the quality of all wool, cashmere or a blend of can’t be beat. 

Pro tip:  look to consignment stores and consignment sites for great finds that will save you a ton of money.  

• Classic Wool Coat (Neutral Color)
• Tailored Trench Coat
• Quilted or Puffer Jacket for Casual Days
• Timeless Leather Jacket

The Tops

Ever since I was a child I have struggled wearing wool and cashmere. And it has always bummed me out.  That said, I do purchase wool and cashmere if I know I can add a layering piece underneath.  My favorite tops and sweaters, however,  are blends that are soft and feel luxurious against my skin.  Whether it’s J. Crew’s supersoft yarn, Eileen Fischer’s organic cotton or a nylon blend, I tend to opt for clothing that feels divine.  

• Cashmere Sweaters (Neutral and Jewel Tones)
• Crisp White Button-Down Shirt
• Turtleneck Sweaters for Added Warmth
• Long-Sleeve Silk Blouse for Dressier Occasions

The Bottoms

My closet is filled with bottoms.  But I don’t typically splurge in this area often.  I do, however, purchase a nice pair or two of denim a few times a year; however, I look for classic styles versus trendy ones, so that I know I will have them and wear them for a long time.  I also invest in a few pairs of quality trousers, the fabric just drapes better and looks more polished.  I also tend to dry clean my more expensive denim and trousers.  

• High-Quality Denim (Dark Wash)
• Tailored Trousers (Neutral and Statement Colors)
• Cozy Leggings for Layering

The Dresses & Skirts

Dresses and skirts are such great classic staples.  And they definitely deserve a place in your classic winter wardrobe.  I don’t purchase many dresses or skirts during the colder months, but I do make sure to have some versatile options that I can easily grab and style quickly.  

• Versatile Wrap Dress
• Long Sleeve Knit Dress
• Elegant Evening Dress
• Casual Shirt Dress

The Footwear

This category is something I have come to appreciate more as I have gotten older; comfort is so important to me now.  I still want to look stylish and dress in my classic style, but if I can’t stand at a cocktail party for several hours in my shoes, I’m not buying them.  Sadly, my back does not care for poor quality footwear.  I have found so many brands that offer high quality footwear that doesn’t break the bank.

• Knee-High Boots (Neutral Color)
• Classic Pumps or Heeled Booties
• Comfortable Flats or Loafers
• Stylish Sneakers for Casual Days

The Accessories

This category is by far my favorite.  I could have a closet just for accessories!  Whether you love to splurge in this category or prefer to save money in this category, accessories can completely transform your look.  And that is why I am such a fan.  Here are some of my favorite splurges and deals.

• Timeless Leather Handbag
• Statement Belt
• Cashmere Scarves (Neutral and Accent Colors)
• Classic Sunglasses
• Elegant Winter Hat

The Layering Pieces

Probably my second favorite category to shop for because I tend to run colder than hotter.  I am always layering my looks, this way I can easily take something off if I get warm.  And layers also have an amazing transformative power when it comes to your classic style, easily taking a dress from a stand alone item to a completely different look just by adding a cardigan.  

• Lightweight Cardigans
• Turtleneck or Crew Neck Sweater for Layering
• Stylish Vests or Gilets

The Evening Edit

• Elegant Blouse for Special Occasions
• Chic Evening skirts or Trousers
• Statement Jewelry (Earrings, Necklace, Bracelet)

The Loungewear & Activewear

 

• Cozy Lounge Set
• Stylish Activewear for Outdoor Activities

Final Tips For Your Classic Winter Wardrobe

Remember, the key to a successful capsule wardrobe is choosing pieces that align with your personal style and can be mixed and matched effortlessly. Happy styling!

• Prioritize neutral colors for versatility.
• Invest in quality fabrics like cashmere and wool.
• Mix high-end pieces with affordable finds for a balanced wardrobe.
• Don’t forget to personalize it with accessories.
• Regularly assess and update your wardrobe for seasonal relevance.

Thanks for stopping by!