16 Fall and Winter Fashion Trends for Men Under $100

Written by Jacob Farmer | October 22, 2021

Here at Savvy, all featured products are thoughtfully handpicked by our section editors. When you purchase something from our links, we may earn an affiliate commission. One last note — any items listed below are in-stock with accurate pricing as of time of publication.

The days are getting shorter, the nights colder, and we’ve got plenty of new fall and winter styles inspired by runway debuts from this year’s Fashion Week. Of course, savvy shoppers know that adhering to every new trend is both costly and, quite possibly, an exercise in futility. That’s why we’ve picked 16 stylish and affordable offers under $100 for guys who want to live in the present without breaking the bank.

Men’s Winter Coats & Jackets Under $100

Oversized Soft-Brushed Patterned Topcoat

1. Oversized Soft-Brushed Patterned Topcoat

Price: $99.99 at Old Navy

This classy topcoat from Old Navy speaks to our modern soft spot for relaxed and oversized outerwear. Available in two versatile colors, blue herringbone and charcoal plaid, you’ll be able to dress it up or down depending on the occasion.

Savings Tip: Enjoy up to 40% off your entire purchase with select Old Navy coupon codes.
Organic Corduroy Shirt Jacket

2. Organic Corduroy Shirt Jacket

Price: $89.50 at Banana Republic

There’s something about corduroy’s classic texture that elevates an otherwise standard jacket to a place of elegance. This offering from Banana Republic doubles as both a jacket and a shirt, making it perfect for layering during the fall and winter. Made from 100% cotton, you can choose from burgundy, navy, and khaki colors.

Double Breasted Belted Trench Coat

3. Double Breasted Belted Trench Coat

Price: $90 at SHEIN

Born out of necessity during World War I, the trench coat has seen many evolutions throughout the 20th and 21st centuries. One thing is for sure: It remains relevant. This khaki trench coat from SHEIN comes with all the belts, buckles, and buttons you might expect from the style, but its lighter cotton fabric won’t weigh you down during the fall season. Some may prefer the traditionally longer length that comes with many trench coats, but we appreciate the year-round appeal of this shorter option from SHEIN.

Trick or Treat 3-Pack Throw Pillow Set

4. Sherpa Fleece Jacket

Price: $118 $100 at the Gap

Fleece has been working its way back into vogue for a few seasons now, and this soft Sherpa knit fleece jacket from the Gap takes that outdoor-inspired look and makes it street-ready. Available in navy and a natural tan, you’ll get the most out of this jacket when contrasting it with other fabrics that bring out the fleece’s unique textures.

Menswear Fall Trends Under $75

Water-Resistant Tech Motion Bomber Jacket

5. Water-Resistant Tech Motion Bomber Jacket

Price: $129.99 $64.99 at Banana Republic

Another outer garment that takes its cue from 20th-century military history, this bomber jacket from Banana Republic includes the classic zippered sleeves, but with an added water resistance for that unexpected burst of fall rain. Constructed from 90% nylon and 10% spandex, it’s also designed for the full range of motion, making it ideal for an active or weekend lifestyle. Get it in black or a deep navy.

Savings Tip: Sign up for Banana Republic emails and receive 15% off your entire purchase, making that winter purchase just a little more palatable.
Cotton Sweater in Striped Garter Stitch

6. Cotton Sweater in Striped Garter Stitch

Price: $64.50 at J.Crew

Just when we think we’ve ascended beyond the eternal debate of horizontal versus vertical stripes, this horizontally-striped sweater from J.Crew pulls us back in. Whether you opt for the heather camel with the navy stripe or the natural shade with the spruce stripe is up to you. Either way, you’ll be rocking a super comfortable cotton sweater made to fit under a jacket or be showcased on its own.

Savings Tip: College students and teachers can enjoy a little added incentive when they shop at J.Crew. That’s because a valid college ID can get them 15% off all orders, both in-store and online.
Cotton-silk Donegal Tweed Henley Sweater

7. Cotton-silk Donegal Tweed Henley Sweater

Price: $69.50 at J.Crew

Okay, the Henley might not be blowing people’s minds on the nearest runway, but there’s a reason they’ve weathered the unpredictable waves of trendy fashion. The simple three buttons at the neckline make it exceptionally adaptable. J.Crew clearly respects the Henley, too, as their variety of cotton-silk Donegal sweaters are some of the more tasteful options you can find. Pick from unique shades like twig, forest, night sky, and ash.

Utility Carpenter Pants

8. Utility Carpenter Pants

Price: $69.95 $55 at the Gap

Perhaps it’s mere reactionary thinking after years of constriction, or maybe designers just got tired of squeezing into their pants. Whatever the reason, looser-fitting and more relaxed cuts have been making their way into stores the last few years, like these utility carpenter pants from the Gap. You’ll get no complaints from us. We love the comfortable stretch canvas weave and the rolled cuffs. These pants are available in a light palomino brown and natural.

Relaxed Taper Corduroy Pull-On Pants

9. Relaxed Taper Corduroy Pull-On Pants

Price: $69.95 $55 at the Gap

We’re back again with another relaxed option from the Gap, this time of the corduroy variety. The elasticized waistband, along with their GapFlex stretch technology, makes these pants exceptionally comfortable, and the tapered leg adds a modern aesthetic to the otherwise simple design. There are currently three colors available: gray cast iron, palomino brown, and new classic navy.

Men’s Winter Outfits Under $50

Original Straight Taper Non-Stretch Jeans for Men

10. Original Straight Taper Non-Stretch Jeans for Men

Price: $44.99 at the Gap

Don’t worry, you don’t have to pick sides when it comes to the cut of your pants. In fact, it may be worth keeping it neutral. These original straight non-stretch jeans don’t scream fashion rebel, but they’ll most likely be a staple in your wardrobe for years to come. And at under $50, that’s certainly worth the financial commitment. Go for the dark wash, or embrace the ‘90s nostalgia with a lighter medium rinse. You can also opt for the ripped-knee variety, but those will cost you an extra 10 bucks. (Seriously, those check in at $54.99.)

Regular-Fit Patterned Flannel Shirt for Men

11. Regular-Fit Patterned Flannel Shirt for Men

Price: $36.99 at Old Navy

A fall wardrobe isn’t complete without a dash of flannel, and Old Navy has 11 great patterns to choose from, like yellow plaid and green buffalo check. Made with 100% cotton, these soft flannel shirts come with buttoned cuffs and double chest pockets. We’ve used the word versatile once before in this article, but it bears repeating for the flannel, which has the ability to add a complementary layer to your autumn attire, or can be buttoned all the way up for a simpler, yet bolder, statement.

Recycled V-neck Cardigan

12. Recycled V-neck Cardigan

Price: $69.95 $55 at the Gap

This cardigan V-neck sweater is not only a quintessential article of clothing for your fall and winter wardrobe, it’s also made with 52% recycled polyester, which helps reduce waste in the clothing industry. Choose from two color options: light gray marl and classic navy.

Savings Tip: In addition to selling highly affordable clothing for all ages and styles, the Gap also has a rewards program called Gap Good Rewards where you can receive bonus points for every dollar you spend, as well as free shipping for orders over $50.
Powerblend Fleece Jogger Pants, 31

13. Powerblend Fleece Jogger Pants, 31"

Price: $40 $30 at Hane’s

Sweats have long been a staple of casual fashion, and these jogger pants are perfect for a trip to the gym, the track, or simply lounging around the house. The tapered leg and ribbed cuffs are also stylish enough to let you wear them around town for errands or outdoor activities.

Cheap Winter Fashion Essentials for Men Under $25

Men’s Standard Fit Denim Long Sleeve Button-Down Shirt

14. Men’s Standard Fit Denim Long Sleeve Button-Down Shirt

Price: $24.99 at Target

It can be hard to get a quality denim button-down under $25, but this long-sleeve from the Goodfellow & Co brand at Target delivers. Choose from black, gray, or light blue denim for a smart-casual addition to your fall wardrobe. While it goes great with chinos during the colder months, you’d be surprised at how easy it is to roll up the sleeves and combine them with shorts during the spring.

Savings Tip: Save up to 30% off already marked-down prices with select Target promo codes.
Lightweight Marled Camp Socks With Double Stripe

15. Lightweight Marled Camp Socks With Double Stripe

Price: $19.50 at J.Crew

Who doesn’t love slipping on a cozy new pair of socks during the colder months? These camp socks from J.Crew are made from a comfortable cotton/nylon blend and are now lighter than previous versions, making them ideal for fall or mild winters.

Knit Beanie

16. Knit Beanie

Price: $15 at Target

Ear warmer, messy hair hider, or just a well-placed accessory, the beanie is a must-have for any fall and winter wardrobe. Dress it down in athletic wear, or use it to complement your winter coat and sweater, this knit beanie from Goodfellow & Co has what it takes to satisfy any occasion.

Sign up for daily deals.

Get personalized inspiration and exclusive deals from your favorite brands straight to your inbox.

We take your privacy seriously.
Read our Privacy Policy

Sign up for our newsletter