How to Dress to Impress in the Fall and Winter

How to Dress to Impress in the Fall and Winter

Those of us who thrive in warm weather may find transitioning to fall and winter style a bit of a drag. But the cooler months are no time to abandon your personal sense of style. In fact, they bring lots of new opportunities for dressing and accessorizing. Think: funky socks, leather boots and jackets that make you feel like a total badass. It’s sad to say goodbye to our shorts and flip-flops, but there’s plenty in store for you year-round style influencers, so embrace the chilly weather as it comes!

Here are our favorite tips for dressing to impress and maintaining some fun and personality this fall and winter:

Lay the Foundation with Solid Base Layers — Cliché as it may be, the breezier months are all about layering. Your favorite comfy V-neck may not be the main attraction this time of year, but it plays an important role in your wardrobe. High-quality basic tees serve as essential base layers beneath cardigans, jackets and long-sleeved shirts, so make sure to lay the foundation with quality garments. Here are some tips for choosing your base layers:

We recommend buying a few poly-cotton casual T-shirts for men in white, gray and black so you’ve got an excellent starting point to work with.

Choose versatile fabrics such as cotton-poly or lightweight wool that you can use to layer beneath sportswear and dress shirts alike.

Remember to keep your base layers slim. If you’re planning on layering up with cardigans and blazers, bulky fabrics and knits just won’t work.

Pair your trench coats and long jackets with tall T-shirts for that perfectly layered look.

Lean Into Your Jacket Game — Jackets are the MVG (most valuable garment) of any well-designed fall and winter wardrobe, so you might want to consider making them a big focus this season. We recommend investing in a couple of timeless, go-with-everything top layers, such as a leather jacket and a denim jacket. But don’t be afraid to top off your looks with statement styles that complete your look, either. If this is more your vibe, hit the local thrift store and try to find a few eye-catching vintage pieces that won’t cost a ton. You can always choose quality pieces from the thrift store and then have your tailor customize them to your figure. This usually doesn’t cost more than $30 per jacket. 

Invest in a Solid Pair of Leather Boots — There is simply no substitute for leather boots in the fall and winter. Not only do they go with everything, but they shield your feet from the cold, slush and snow. You’ll want to make sure you have a few boots in different heights, including the typical work boot height, as well as Chelsea and chukka boots that are a bit shorter at the ankle. Make sure to style your leather boots with a pair of perfectly tailored boot-cut or slim-fit jeans that don’t drag on the floor, cuffing them at the bottom if needed. This is another time to take full advantage of your local tailor’s expertise!

Know Some Classic Combos — Don’t get us wrong, there’s no one-size-fits-all approach to dressing. With that said, there are a few cool combinations that simply always look great together. Keep these pairings in your back pocket so that you always have an amazing cold-weather look in your arsenal:

Scarf and blazer or suit. When it’s not so cold out that you can wear a blazer as a top layer but it’s nippy enough that you don’t want your whole neck exposed, pull out the timeless scarf-blazer combo. Take it further by styling your scarf with a suit and tie for more formal occasions. 

Slim-fit jeans and combat boots. The slim-fit jeans and combat boot combo is a true power move that’ll make you feel like a total boss. Cuff your jeans at the ankle or just above for an even cooler look.

Turtleneck and puffy coat. When the weather really starts to chill out, you’ve got to double-up on the warmth. Go for a turtleneck paired with a puffy winter coat for head-to-toe coziness and style.

Denim jacket and hoodie. Ideal for those milder fall and early winter days, the denim jacket and hoodie combo is all about creating cool, edgy style with a comfortable flair. If it wasn’t obvious, make sure to let the hood stick out of the back of your jacket for that perfectly punk aesthetic.

Hello, Funky Socks — Here’s one thing we love about cold-weather dressing: fun socks. Great for the workday or even formal events, novelty socks help you add a bit of fun into your wardrobe when it may feel a little bit stiff or boring. You can take this in any direction you please, from bright colors and subtly funky patterns — hello, argyle and animal print — to all-out novelty styles featuring graphics of your favorite fictional characters and beyond.

Get Cozy with Scarves — We think scarves are among the most underrated fashion accessories, especially when it’s nippy out. A classic plaid or houndstooth scarf adds a preppy, polished look to whatever you’re wearing, while a knotted black neck scarf can bring some edge when tucked into a leather jacket. If you prefer more boho to preppy, take some cues from scarf king Lenny Kravitz and go over the top with a massive knit number. 

Just because it’s cold outside doesn’t mean getting dressed has to be all about utility. The reality is that the fall and winter bring with it cold, wind and snow, so there are some important things to consider when getting dressed. But there are some great ways to create impressive looks at this time of year that keep you warm and make you look cool.


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