Transitioning from Fall to Winter: 6 Wardrobe Essentials

Snow-ready weather is in full effect, and it’s time to start transitioning your wardrobe from fall to winter—and we aren’t just talking about buying a few ugly holiday sweaters. Fashion under forty degrees can feel bulky or cumbersome, but with the right winter essentials, you’ll feel chic and high-fashion without sacrificing comfort or warmth. 

When it comes to making a successful transition, it’s all about repurposing and smart shopping. Invest in these six basics to enhance your wardrobe, regardless of the season. Plus, these items can be worn again next fall! 

1. Statement Coat

Image source: Pinterest Etsy 

In addition to your puffy, down jacket (a must for those cold days), you’ll want a jacket that leaves an impression. A statement coat is perfect for going out or dressing up an outfit. While peacoats are certainly one of the more traditional and classic options, you could opt for a leather jacket to add a little more edge. Alternatively, look for a patterned option. I snagged a leopard print JCrew coat on sale last year and haven’t looked back since!  

Remember that this coat needs to layer well. Longer lengths are often more versatile and easier to pair with shirts and sweaters of various sizes.

2. Thin Layers

To avoid bulk and keep your style in check, maintain an assortment of thin layering clothes to add dynamic elements to your outfit without sacrificing personal warmth. Nineties babies can remember when our Mom made us wear a turtleneck under a sweater. Well, that’s back on trend now—embrace it! Consider a classic turtleneck or long-sleeve shirt as your secret weapon underneath a boyfriend-fit sweater, bulky knit, or oversized cardigan. 

Check out these layering options. As a bonus, these shirts will look great on their own tucked into high-waisted pants or under overalls during the fall. 

3. Boots

Whether they’re knee-high or ankle-length, boots should be a staple of your winter wardrobe. More than a fashion statement, they’re the perfect shoe for layering warm socks and feeling winter-ready.

Purchase neutral-color boots for a versatile piece of your wardrobe that can transition from day to night, depending on the occasion. I’d consider investing in two types—an all-weather boot (try these chic options) that can take you from rain or snow. Then, a pair that is less functional but more stylish (think healed booties or leather moto boots). These can be worn on those mild fall and winter days but will offer more protection on a night out than a pair of stilettos.  

4. High-Fashion Hats

Hats are the perfect accessory to keep your head warm and even hide a bad hair day. Wide brim fedoras and fitted beanies will become your best friend during the winter months, bringing a point of interest to your outfits and protecting your crown. To make it more chic and European, you can opt for a beret (which is still trending thanks to the Emily in Paris phenomenon). 

The best part about hats is that they’re an inexpensive way to accessorize an outfit, so you can invest in multiple options and flirt with different trends.  

5. Blazer

Built to go from day to night and everything in between, blazers can be the perfect power-statement to showcase confidence, boldness and a chic sense of style. For a more business-professional look, pair a blazer with a muted pair of pants and a simple white shirt. When it’s time to go out with your friends, consider an oversized blazer as the perfect complement to your little black dress (or those pleather leggings you’ve been coveting). 

6. Chunky Sweaters

Chunky sweaters are the easiest way to offset a sleek skirt or tight pair of pants, providing balance and proportion to your outfits (and also keeping you toasty). Additionally, the oversized look lets you seamlessly layer underneath for added warmth. 

Look for a few options that aren’t too winter-specific (like fleece or sherpa material). That way, you can repurpose those lighter sweaters in all seasons. For example, I invested in an L.L. Bean light-weight cotton pull-over and I wear it all year long, even with shorts!  

Steal these tricks to look runway ready:

  • Don’t be afraid (or self-conscious) to size up. An XL budget-friendly sweater can offer the same oversized slouchy look as pricier alternatives.
  • If you need to “crop” your sweater to the perfect length, give this trick a try from fashion blogger JesswithLess, to shorten the knit without making a single cut or sewing a stitch. 

Building Your Perfect Fall to Winter Outfits 

To build a closet of winter essentials, look for versatile clothes and can be worn with several different looks. Start small, and focus on neutral colors that can mix and match with a few statement pieces thrown in. When you want to invest in a piece, do your research. It takes five minutes to find reviews online and they can help you decide between a “worth it” or wonky item. 

If you’re ready to transition your wardrobe from Fall to Winter but want to reinvent your style, consider taking some fashion advice from expert Tan France, popular stylist and TV personality. “Back in the day when I couldn’t decide on what I wanted to look like, I would refer to the people that I gravitated toward,” he shared. “I would look at what they were wearing and I would think of that when I went shopping. So that’s what I encourage our heroes to do on the show: Find somebody in the media that you think dresses great or has a lifestyle that you gravitate towards and think of that when you go shopping.”

No matter your style or fashion inspo, confidence is the one piece that will make your outfit stand out. So wear your new winter creations with pride. Whether you’re rocking athleisure while WFH, feeling yourself with mirror selfies, or strutting down the snowy streets.

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