The Only New England Fall Fashion Guide You Need (His & Hers)

Looking for a Fall fashion guide for New England? You’re in the right place!

In this blog, I share Fall wardrobe essentials for both women and men so you can look cute all over New England while staying warm.

I also share how to coordinate outfits as a couple, what to wear for outdoor adventures, as well as what to wear to get the stylish “New England Look” this Fall. Throughout the guide, I’ve created sections for “his & hers”, which I hope you find helpful.

And hey, ladies if there’s something you want your man to wear, don’t be afraid to share this blog with him. 😉

So, let’s get started! This is your Fall Fashion Guide for New England!

What is Fall Like in New England?

For those of you have never been to New England, I’m so excited for you. It’s the perfect place to escape this Fall whether you’re looking to visit the coast or the country.

There’s so much to do in New England in the Fall!

Wander through apple orchards to pick your own crisp, juicy apples or explore pumpkin patches where you can choose the perfect pumpkin for carving. There are also a lot of farm stands you can stop at on the side of the road for fresh pies, jams, and local cheeses.

In charming seaside villages, you’ll find adorable cafes, boutique shops, historic inns, and lighthouses, while the countryside invites you to embrace the great outdoors, which I help you pack for later in this blog.

In the mountains, you can hike through trails covered in crunchy leaves, discover hidden waterfalls, or go horseback riding. Or, set off on a Fall roadtrip and take a scenic drive through covered bridges to check out New England’s colorful foliage blazing with bright hues of red, orange, and gold, followed by a lakeside picnic.

After a day of adventure, get back to your cozy cabin or mountain lodge and snuggle up with a soft blanket over a toasty fire and indulge in smores or a cup of hot apple cider while the cool, crisp air reminds you why Fall in New England is simply magical.

You might also like:  

Fall in New Hampshire: 9 Fun New Hampshire Fall Activities

New England Climate in the Fall

When I moved to New England over a decade ago, I was totally smitten… And then this Cali girl had a wake-up call. The weather was a total change from what I was used to in sunny, Southern California!

In my experience as a New Englander for over a decade, living in almost every single state in the region (except Rhode Island), I can say that New England’s Fall temperatures usually hovers between the 50’s & 60’s, although it can get down to the 30’s & 40’s on a really chilly day.

You could be totally warm in one part of New England, then experience wind, rain, and even sometimes snow in another part. It’s what makes packing a bit tricky.

September is usually the warmest Fall month and can even show some sunshine. This is when Fall activities are the most fun in my opinion.

What to Wear in New England (His & Hers)

Now that you know the climate, here’s how you should dress in New England this Fall.

Since New England’s weather can be as unpredictable as it is beautiful, your wardrobe needs to be on point. Whether you’re wandering through adorable coastal towns, taking in the stunning fall colors, or getting cozy mountainside, layers are a must.

Ladies first…

A Girl’s Fall Wardrobe Guide

Fall is the perfect time to mix up your style with snuggly knits, stylish scarves, and cozy layers. And if you’re aiming for the New England preppy girl look, a string of pretty pearls. This guide is all about making those outfits effortlessly stylish and totally you.

Let’s find those must-have pieces that make transitioning from sunny days to crisp evenings a breeze.

Wardrobe Essentials For Her – Upper Body  

Sweaters

A classic layering piece that adds warmth and elegance to any outfit. Cozy up in a cashmere turtleneck, or a merino wool or cableknit sweater. Half-zip and oversized sweaters in soft neutrals or rich Fall shades are trending statement pieces as well.

Outfit idea: Start with a classic Cashmere Turtleneck (LL Bean) or a Cashmere Turtleneck Tank for a luxurious feel, perfect for layering under a wool cardigan or a stylish oversized blazer. You can also do the popular Band Jacket (Tommy Hilfiger X Gigi Hadid) for a sophisticated look.

Ponchos & Capes

Nothing says Fall like a poncho or cape! Easy to throw on and effortlessly chic, these stylish pieces offer both warmth and a dramatic flair, perfect for layering over slim-fitting tops.

Pair a knit, solid-colored poncho with a turtleneck and leggings or skinny jeans for a modern look. Or, for a relaxed, bohemian vibe, choose a patterned cape over a knit dress. Dress a poncho or cape up with ankle or knee-high boots with heels for a polished look.

Blazers

Whether they’re structured or oversized blazers in tweed or wool add a refined touch to any outfit.

Outfit idea: Layer a blazer over a turtleneck or cashmere sweater, paired with tailored pants for a polished look or dark-wash jeans for smart-casual style. Finish the look off with a statement belt or silk scarf and voila!

Shirts & Tops

These are perfect for wearing by itself on casual, indoor days or layering.

For a lighter layer, wear a long-sleeve cashmere, merino wool tee, or even a flannel plaid shirt under a sweater, vest, wool blazer, cardigan or light jacket (denim, quilted, fleece, puffer)

Shop: Plaid Flannel Shirt (Eddie Bauer)

Vests

For a lighter layer, a vest is perfect paired with a base layer like a merino wool shirt, fleece, sweater, or flannel shirt.

Throw on a quilted or wool vest over your base layer, which adds warmth without bulk, creating a chic, layered outfit perfect for the season.

** This Amazon best-selling battery powered heated vest is a best seller! Wear on chillier nights, it’ll keep you warm for up to 10 hours on a single charge, perfect for those nature outings.

Sweater & Wrap Dresses

Fall is the perfect time for cozy yet stylish dresses. Soft, knit dresses are comfortable and chic, while wrap dresses are flattering and versatile. Choose warm tones and pair with tights and boots.

Outfit idea: Try a knit dress with knee-high boots or a midi sweater dress under a tailored coat.

Wardrobe Essentials For Her – Lower Body  

Skirts

Choose an A-line or pencil skirt in luxe materials like leather or suede, perfect for pairing with tights and boots. Maxi Skirts in heavy fabrics like wool or cotton are also great choices and look best with a sweater or top tucked in.

Style Tip: Pair a long skirt with a pair of loafers or mules. Bonus points for going monochromatic with a plaid skirt and these matching Cole Haan mules.

Pants

• Corduroy Pants

Corduroy pants offer a soft, textured feel and a chic, vintage-inspired look that effortlessly complements cozy sweaters and ankle boots. Choose earthy tones like rust, maroon, olive, or mustard.

• Tights & Leggings

When wearing skirts or dresses, layer with wool tights or fleece-lined leggings. Commando Control Top Tights are a great option for warmth and comfort.

Outfit idea: For a comfortable yet stylish look, pair leggings/tights with oversized sweaters and boots. And if you really want to make a statement, try faux leather leggings. They’re perfect for adding an edge to your Fall wardrobe and can be dressed up or down.

• Dark Wash Jeans

I love these Madewell vintage skinny jeans with their edgy, 90’s vibes. But, depending on the look you’re going for or the shoes you’re wearing, you can also find amazing jeans in all different styles and shapes from a high waisted flare jeans or a bootcut to a jegging pant with a snug fit or boyfriend jeans.

I myself have gotten a booty that tripled in size over the last few years when my mid-20s body decided to gain the “not a freshman, freshman 15”. What can I say, I was delayed in life. So, yes… these curves seemingly crawled up on me overnight, it was weird but awesome. Even though I made the mistake of donating literally 80% of my pant collection that took over a decade to acquire, I discovered some styles I really like for my body!

Then, I started doing pilates and lost my ass again, lol.

So, you never know. I recommend not giving pants away and instead, adding different sizes to your wardrobe if you’re like me and easily lose/gain trunk junk.

Classic blue jeans, high-waisted jeans and wide-leg pants are perfect for Fall. Go for Levi’s Highrise Bootcut Jeans or Signature Bootcut Jeans, for a darker wash. You can also go for overalls for that cute farm girl look. 😉

Shoes

Ladies, it’s important to remember that New England has a lot of historic, uneven cobblestone pavements that your shoe can get caught in. Therefore, I would not recommend wearing super high heels or a skinny, pointy heel.

Lucky for you, there are lots of great shoe options.

Sam Edelman is one of my favorite shoe brands. I’ve had many of my same Sam Edelman shoes for years.. Not only are they classic and never go out of style, they withstand hours of wear and go with so many different outfit looks. They’re also surprisingly affordable for the quality. Not sponsored, I just love Sam Edelman! 🙂

For Fall, there’s nothing cuter than an ankle or knee-high boot. Try a style with sleek leather or suede. It looks great whether you wear them with a dress, skirt, or skinny jeans.

Consider Sam Edelman’s Jazmine Chelsea Boots or Clive Embellished Riding Boot.

For a lighter, closed toe shoe with some old school style, try a mule, oxford, loafer, or a classic ballet flat. One of my favorites is Tory Burch’s Minnie Travel Ballet Flat.

And of course, it wouldn’t be sweater weather without a warm and cozy UGG boot in Classic Short Boot or Tall Boot.

These wool socks by Carhartt are seriously a game changer. Not only are they inexpensive, they work like a charm! Because I get really cold feet due to my poor circulation w/ Lupus, I’ve had issues finding socks that kept my feet warm. Not only do these wool socks do the job but they last a long time and are easy to wash. I swear by them.

For thicker Carhartt socks for extra chilly days, these are a top Amazon pick.

Jackets & Coats

A great coat is your Fall essential, effortlessly pulling together any outfit while keeping you warm and stylish through crisp Autumn days.

• Trench Coats: A timeless classic, perfect for layering over everything from casual outfits to workwear. (shop here)
• Leather Jacket/Coat: Try a lambskin or suede leather jacket for a super chic Fall look. I love my knee length coat. (shop here)
• Quilted Jackets: Lightweight yet warm, ideal for those in-between weather days. (shop here)
• Denim Jackets: A versatile piece that adds a casual, laid-back touch to your wardrobe and great for grabbing a bite or going for a horseback ride. (shop here)
• Waterproof Jacket: For rainy days, choose a versatile, lightweight jacket. This one has a removeable hood.
• Wool Coats: Tailored wool coats in classic shades like camel, navy, or charcoal are a must-have for colder days. (shop here)
• Peacoats: Originating in the military, women’s peacoats bring a touch of timeless, structured elegance to any fall outfit. A double-breasted wool coat is perfect for colder climates, combining warmth with a heritage of classic style. (shop here)

Stylish Fall Accessories for Women

• Belts: Wide, statement belts to cinch your waist over dresses or coats, adding a stylish finish to your outfit.

• Scarves: A large, oversized wool or cashmere scarf in plaids, solid colors, or houndstooth patterns adds warmth, a pop of color and pairs well with any outfit.

• Hats: Wide-brimmed felt hats (a la Schitt’s Creek’s Alexis), classic berets, and knit beanies are perfect for adding a chic touch. Knit hair headbands also look super cute.

• Gloves: For for leather or wool with cashmere lining which look stylish while keeping your hands warm.

• Crossbody Bags: Functional and stylish, perfect for keeping your essentials close while on the go.

Ladies, if you know a man who could benefit from some style tips this Fall, (including your own), share this blog with him. 😉 Now we dive into a man’s Fall wardrobe….

A Guy’s Fall Wardrobe Guide

Now it’s your turn gentlemen. I must admit, I love men’s fashion just as much as women’s fashion.. I used to love shopping for my ex’s wardrobe.

As the weather cools down and the leaves change, it’s the perfect time to level up your fall wardrobe.

But, that doesn’t mean you have to break the bank, I’ve also included some budget friendly options as well.

Fall is all about layering up with stylish, cozy pieces that keep you warm and looking sharp.

Whether you’re out for a casual day or need to dress up a bit, the right flannels, boots, and jackets will not only have you ready for anything this season, but have you turning a head or two. 😉

Wardrobe Essentials For Him – Upper Body  

Shirts

Start with a classic Fall staple that keeps you warm and comfortable like a Land’s End flannel shirt or a Calvin Klein long-sleeve henley, which are both versatile base layers perfect for layering or wearing on its own. Top it with a quilted vest or a lightweight jacket for added warmth without bulk.

Sweaters

The ultimate Fall staple, sweaters offer comfort and style, whether you’re cozying up in a thick cableknit, a wool crewneck sweater, or layering a sleek cashmere turtleneck under your favorite coat.

Brooks Brothers has great styles for men. Choose textured sweaters in shades like gray, navy, or olive.

Shop: Cashmere Turtleneck (J.Crew ), great for layering over button-down shirts.

Vests

You have fleece, quilted, puffer…. For a stylish look that’ll keep you warm outdoors, a quilted vest is perfect for layering with a fleece, flannel shirt, or a light sweater.

Outfit idea: For a casual yet polished look, try the Cole Haan Water Resistant Puffer Vest. Pair with a light jacket like the Barbour Waxed Jacket and you’ll be able to handle the unpredictable New England weather with style​. 😉

For extra chilly days, this battery powered heated vest for men is a very popular Amazon pick and keeps you warm for up to 10 hours on a single charge. Perfect for those long Fall days exploring outdoors. 😉

Blazers

A blazer paired with a sweater goes a long way. In perfect Fall fashion, try a blazer in suede, corduroy, or tweed herringbone or with a bold pattern like plaid. A blazer with suede patches on the shoulders or elbows can also give a simple blazer that nostalgic vintage look synonymous with Fall.

Outfit idea: Try a vest underneath your blazer and top off the look with a bow tie.

You might also like:  

Vermont in the Fall | Your Guide to the Perfect Vermont Fall Getaway

Wardrobe Essentials For Him – Lower Body  

Pants

• Dark Denim Jeans

For a sleek, put-together look, opt for a slim or straight-leg jean in dark washes like Levi’s 511 Slim Fit Jeans, which offers a cozy fit, perfect for everyday wear.

• Corduroy Pants

For a more relaxed vibe, consider LL Bean’s corduroy pants. For added texture and warmth, choose corduroy pants in rich, autumnal colors. You can also go for a monochromatic style here to match your sweater or vest or coat.

• Chinos

Versatile and comfortable, chinos in earthy tones like khaki, olive, or brown are a Fall essential. (shop: Nordstrom | Amazon)

• Cargo Pants

For a more casual, functional option, cargo pants are perfect. With plenty of pockets and a relaxed fit, they’re great for outdoor adventures or a laid-back weekend look. Very military chic. 😉

• Wool Trousers

For a more sophisticated look, try wool trousers in a tweed material.

Shoes

Opt for versatile that can handle both city streets and nature trails. Pair with wool or cashmere socks for warmth.

View this post on Instagram

A post shared by Trey Bryant (@treybryantstyle)

• Leather Sneakers

A polished alternative to regular sneakers, perfect for casual fall outings. Try Cole Haan’s Grand Crosscourt Ii Sneakers.

• Chelsea Boots

Choose sleek leather or suede boots that can be dressed up or down and can handle varied terrain so you can wear them in the city or on a hiking trail. For a stylish boot, consider Clark’s Suede Jaxen Chelsea Boots or, for something a bit more rugged, Blundstone’s Chelsea Boot.

• Motorcycle / Combat Boots

This give a rough, edgier look. Pair with skinny jeans and a leather jacket or blazer.

Jackets & Coats for Men

Wool Overcoat
A classic choice for dressier occasions, offering warmth and style. Opt for neutral colors like grey or camel for versatility. Try London Fog’s Classic Fit Signature Wool Blend Overcoat. For a shorter length, try Kenneth Cole’s Wool Top Coat.

Peacoat

Ideal for a sophisticated yet casual look. This double-breasted peacoat by Van Heusen features wide lapels and works well with jeans or chinos.

Field Jacket
Perfect for outdoor activities, a field jacket is durable and functional with multiple pockets. Choose muted earth tones for a classic look. (shop here)

Stylish Fall Accessories for Men

Fall accessories are all about layering and adding eye catching details to your outfit. If you’re the kind of guy that likes a little somethin’ extra, add a bow tie to jazz up your vest or suit jacket. Here are some more ideas….

Watches

Men can’t go wrong with a nice watch. (Ladies, it also makes the perfect gift ;))

Rugged and practical, field watches like the Seiko SNK809 with earthy tones and durable straps are perfect for Autumn adventures, while the Omega Speedmaster offers a touch of sophistication. Vintage watches with a brown or tan leather strap, retro designs, and patina finishes can add nostalgic flair that pairs well with Fall’s classic aesthetic.

Scarves

Keep warm and stylish with a cashmere scarf, perfect for layering over a peacoat. Or, a wool scarf by Pendleton or Mulberry. Opt for neutral tones like charcoal, navy, or camel, or try a classic tartan pattern.

Hats

Depending on your style, there are lots of different hats a guy could go for. If you usually wear a ball cap, change it up this Fall and go for a ball cap style with leather or tweed details instead.

If you want to take it to the next level, try a Lambskin Leather Ivy Newsboy Cap or a sleek fedora. If you want to keep it simpler, a basic knit North face beanie always does the trick.

Gloves

Leather gloves with a cashmere lining are perfect for keeping hands warm without sacrificing style. Consider these Italian made leather gloves by Brooks Brothers, which are both functional and sleek.

Belts

A suede or leather belt looks super sharp. Consider shades of brown or tan. Brands like Levi’s or Lucky Brand have stylish options.

Fall is the perfect time to cozy up with your partner and show off some serious style as a duo. Coordinating your outfits as a couple doesn’t mean you have to look identical (unless you’re into that). It’s more about syncing your vibes and looking effortlessly stylish together.

Here’s how you can nail that coordinated look without going overboard.

Color Match, But Not Too Much

• Pick a Palette: Start by agreeing on a color scheme that you both like. Neutrals like beige, gray, and navy are super versatile, but fall tones like burgundy, mustard, and olive green can really make your outfits pop.
• Complement, Don’t Clone: Instead of wearing the exact same colors, try complementary shades. If you’re rocking a mustard sweater, maybe your partner goes for a deep burgundy jacket. You’ll look connected without being too matchy-matchy.

Layer Like Pros

• Twinsies on Outerwear: Fall is all about layers, and matching coats or jackets is an easy way to sync up your look. Think leather jackets, trench coats, or cozy flannels that both of you can vibe with.
• Mix It Up: If you’re not into matching exactly, play with textures. Maybe one of you wears a chunky knit sweater while the other rocks a sleek wool coat. Different textures can look amazing together and show off your individual styles.

Accessories That Say “We’re Together”

• Small Matching Details: Subtle accessories like matching scarves, beanies, or gloves can tie your looks together without being too obvious. Go for similar colors or patterns to keep things coordinated.
• Balanced Statement Pieces: If one of you is going bold with an accessory—like a cool hat or a standout bag—let the other’s outfit be more understated. It’s all about balance, so you both shine without outshining each other.

Dress for the Occasion

• Casual Hangouts: For a laid-back day, think cozy but stylish. Both girls and guys can’t go wrong with classic flannels, comfy jeans, and some sturdy boots that can handle everything from cobblestone streets to muddy trails. Pair your jeans with comfy sweaters or casual button-downs in colors that vibe together. And don’t forget a warm jacket for those chilly nights, plus a cute scarf or hat to nail that New England vibe.

• Fancy Nights Out: When you’re dressing up, coordination is key. If one of you is going all out in a suit, the other could wear a dress or outfit in a matching or complementary color. You’ll look like a power couple without being over the top.

Keep It Balanced

• Subtle Coordination: If you both love bold patterns or bright colors, pick just one statement piece each and keep the rest neutral. For example, if one of you is wearing a patterned shirt, the other could wear a solid color that pulls from the pattern.

• Layering for the Win: Layering is the perfect way to play with patterns and colors. Try wearing a patterned shirt under a solid jacket or coat, and coordinate that with your partner’s outfit.

Remember, coordinating your outfits is all about having fun and showing off your connection. It’s not about matching exactly but creating a look that complements both of your styles.

That’s a Wrap!

I had a blast creating this his & her Fall wardrobe guide for you!

Going to New England? What looks do you want to wear this Fall? Comment below and subscribe to the blog for upcoming retreats & trips I’m hosting, travel inspiration, tips & travel rewards for free trips!

Happy traveling!

If you enjoyed this post, you might also like:

20 Helpful Tips for Traveling with a Chronic Illness

Rhode Island in the Fall: Make New Discoveries this Fall