How to Dress Warmer this Fall and Still Look Great


Once the fall season hits, it starts getting cooler each week. Extra layers are necessary to keep warm during crisp mornings and cool evenings. But, you need to ensure your undershirts look stylish in case you need to shed the jacket during warm afternoons. 

Layer up with a long sleeve henley, a comfy cardigan, and some fitted jeans. Fall fashion combines staple pieces to create one cohesive outfit that looks great while keeping you warm and cozy. 

It’s all about snuggling up in simple layers to create an effortlessly cozy feel without looking big or bulky. This guide can help you pull from your closet to create unique fall ensembles that stay true to your sense of style.

Start with the Basics: 5 Staples to Build Your Look  

Before you start layering up your outfit, you need to start with the basics. A quality shirt and fitted pants will help you add warmer layers without bulking out. If you wear a printed shirt or colored pants, keep the top layers neutral to keep the ensemble from being too loud. Stick to neutral colors as much as you can when beginning an outfit. 

1. Fitted T-Shirt 

Choosing a well-fitting t-shirt under fall layers will keep you looking trim. Loose, baggy t-shirts can bunch and bundle under layers giving the illusion that you are bigger than you actually are. Find a brand and cut you like that flatters your body and buy extras, so you always have one clean. 

2. Long Sleeve Henley 

A long sleeve henley can add more flair to an outfit than a classic t-shirt. It’s similar to polo, but without a collar. The three buttons draw the focus to the chest, and the material is warm enough for fall but breathable enough, so you don’t overheat once the temperature rises midday. 

3. Plaid Flannel Shirt 

Flannel is the perfect fall layer for early fall. Try your flannel with a rich brown blazer and a pair of khakis for a more buttoned-up look. When the weather is right around 60 degrees, and you don’t quite need a jacket, style a flannel with your dark wash jeans and long sleeve henley. 

4. Dark Wash Jeans 

As the leaves change, you’ll want to wear darker colors to match the season. A black or deep blue pair of jeans will match any jackets and shirts you choose to layer with and better suit the fall color palate. 

5. Men’s Joggers

Joggers can keep you warm on your morning walk, run, or hike. Plus, the tapered legs keep them from looking too much like sweatpants. Style them beyond your workout by pairing them with a fitted tee and bomber jacket to grab a coffee. 

In whichever pants you build your look from, choose a fitted style through the leg to keep it looking trim as you add extra layers to the ensemble. 

Consider Your Fabrics

As the fall months progress, the temperature will continue to dip. You’ll want to choose fabrics that will keep you warm but stay breathable enough to keep you comfortable in the office. 

Cotton can work for inner layers, like long sleeve henleys and t-shirts, but they won’t wick away moisture. Staying dry is an essential part of keeping warm. If you think you’ll sweat, you may want to choose a spandex workout shirt that will keep you dry.

Wool is one of the warmest fabrics you can find. It’s made from sheared animals and has natural insulation and moisture wicking, making it great for sweaters, scarves, socks, and gloves. You could opt for fleece as a warm synthetic option made from polyester.   

Layer Up: 5 Fall Outerwear Must Haves 

Once you’ve started your look with a pair of pants and a long sleeve henley, flannel, or simple cotton tee, it’s time to start layering.

1. Wool Sweater 

A half-zip wool sweater with a pair of trousers and a button-down makes for a simple business casual look. Effortlessly go from the office to happy hour at the bar and stay looking fit. You could also try a shawl neck cardigan. The thick neckline will keep the sweater from looking too feminine. Rock it with a pair of jeans and a long sleeve henley for a casual fall look. 

2. Bomber Jacket

 Pair that same long sleeve henley with a black bomber jacket and your dark wash jeans for a night out with boys. 

3. Down Vest 

A down vest is a fantastic layer to wear under a heavy coat to keep your torso warm during winter and on its own during the fall. Throw a fitted-down vest over a long sleeve henley with your joggers and a pair of chukka boots to run a few errands. 

4. Leather Jacket 

Add a bit more attitude to your fall outfits with a leather jacket. Keep it classy with a chestnut brown fitted leather jacket, Chelsea boots, and a patterned button-down, or layer over a plaid flannel with some distressed denim, and go for the 90s grunge look.   

5. Chore Coat  

Initially designed for working men, these tough canvas coats will keep you warm while staying on trend. They were made for farmers and factory workers, so you know they’ll stand up to fall’s inclement weather.  

Keep it Chic from Head to Toe 

Once November hits, you’ll need to add a hat and gloves to keep warm. A beanie will play well against a long sleeve henley and joggers for a casual trip to the grocery store or to keep your ears warm on a brisk morning run. 

Keep your fall outfits looking sleek from head to toe by pairing your jeans, long-sleeve henley, and vest with a chukka or Chelsea boot. Try a black leather combat boot with your leather jacket and flannel if the grunge look is more your style. 

Take the time to consider every element of your outfit, from head to toe, and you’ll look stylish while staying warm this fall.