There’s something about fall fashion that always makes getting dressed feel a little more fun. Give me a great pair of jeans, a beautiful jacket and a pair of boots and I’m happy.

But as much as I love putting together a great outfit, comfort matters — especially when I’m traveling. I don’t want to pack an outfit that looks amazing for dinner but is miserable to wear while walking around all afternoon. And I definitely don’t want to bring an entirely different outfit for every part of the day.

My favorite fall outfits are the ones that can do both.

Think great denim, simple layers, classic trench coats, comfortable shoes and a few accessories that can take an outfit from sightseeing and shopping during the day to cocktails or dinner at night.

And you don’t have to spend a fortune to get the look. I love mixing investment pieces with affordable finds -an inexpensive white tee with a beautiful bag, American Eagle jeans with a great coat, or an Express top with my Tieks flats I’ve owned for years.

Here are seven chic fall outfit ideas that are comfortable enough to wear all day and polished enough to take you straight into the evening.

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1. Straight-Leg Jeans + White Tee + Trench Coat

If I could only pack one fall outfit for a weekend away, it would probably be this.

Start with a really good pair of straight-leg jeans and a simple fitted white tee. Add a classic trench coat and finish the look with ballet flats or a comfortable ankle boot.

It’s effortless, but the trench instantly makes the entire outfit look more polished.

I wear American Eagle and Express denim quite a bit, and this is exactly where I don’t think you need to spend hundreds of dollars on jeans just to get a great fit.

For daytime, I’d carry a larger tote and keep the accessories simple.

For dinner, swap the tote for a smaller structured bag, add gold jewelry and a great lipstick. You don’t even have to go back to the hotel and change.

SHOP THE LOOK

SAVE: Affordable trench • American Eagle jeans • fitted white tee • Tieks flats

SPLURGE: Premium trench • designer denim • leather loafers • structured bag

DAWN’S MIX: Save on the tee and jeans. Put the money into the coat, shoes or bag you’ll wear for years.

2. Cropped Trench + Dark Denim + Ballet Flats

A cropped trench gives you the same classic look as a traditional trench but feels a little more casual and modern.

I’d pair one with dark straight-leg or slightly wide-leg jeans, a simple cream or black top and my favorite Tieks ballet flats.

This is such an easy outfit for traveling because nothing feels overly fussy. You could wear it to brunch, spend the afternoon exploring a new town and still look completely put together walking into a nice restaurant that evening.

For nighttime, add a belt, switch to a smaller bag and layer on a few pieces of jewelry.

SHOP THE LOOK

SAVE: Cropped trench • dark denim • basic knit top • ballet flats

SPLURGE: Premium cropped jacket • designer flats • leather handbag

DAWN’S MIX: This is one I’d save on the jacket if I found a great affordable version and splurge on beautiful flats that are actually comfortable like Tieks. 

3. Jeans + Striped Sweater + Flats

There are certain pieces that just never look dated, and a striped sweater is one of them.

Pair a cream-and-black or cream-and-navy knit with your favorite jeans and loafers for one of those outfits that looks like you tried harder than you actually did.

And that’s exactly the kind of outfit I want when I’m traveling.

Throw a trench over it if it’s chilly, add sunglasses and carry a roomy tote during the day.

At night, tuck the sweater slightly into your jeans, add a belt and gold earrings and swap the tote for a smaller bag.

Simple, comfortable and chic.

SHOP THE LOOK

SAVE: Striped knit • straight-leg jeans • flats

SPLURGE: Cashmere striped sweater • premium denim • 

DAWN’S MIX: I’d happily wear affordable denim with a beautiful sweater or handbag here.

4. Wide-Leg Jeans + Button-Down + Sweater

This is one of my favorite ways to get that classic, slightly preppy fall look without feeling overly dressed.

Start with wide-leg jeans and a crisp white or pale blue button-down. Wear a sweater normally, layer it over the shirt or simply drape it over your shoulders.

Add Tieks ballet flats during the day.

The combination is comfortable enough for walking around but still feels polished enough for lunch somewhere nice.

For evening, tuck in the shirt, add a leather belt and swap the flats for ankle boots.

SHOP THE LOOK

SAVE: Wide-leg jeans • cotton button-down • crewneck sweater • Biscotti Tieks

SPLURGE: Cashmere knit • premium denim • leather belt • designer flats

DAWN’S MIX: Spend where you’ll notice quality. A beautiful sweater and leather accessories can elevate even very inexpensive basics.

5. Dark Jeans + Black Top + Camel Blazer + Ankle Boots

This is my day-to-night fall outfit.

Dark denim automatically feels a little dressier, especially when you pair it with a fitted black top and camel blazer.

During the day, wear comfortable flats and carry a tote.

Before dinner?

Switch into ankle boots, add earrings, grab a smaller bag and you’re done.

No complete wardrobe change required.

This is exactly the kind of outfit I like packing for trips because every piece can also be worn separately with something else in my suitcase.

SHOP THE LOOK

SAVE: Dark jeans • fitted black top • camel blazer • ankle boots 

SPLURGE: Wool blazer • premium denim • leather boots • investment handbag

DAWN’S MIX: I’d wear my favorite affordable jeans and top and let the blazer, boots and bag do the heavy lifting.

6. Black Pants + Soft Knit + Ballet Flats

You don’t have to wear jeans every day to be comfortable.

A pair of relaxed black trousers with a soft cream, camel or grey knit can be every bit as comfortable while looking considerably more polished.

Add ballet flats or loafers and a trench during the day.

For evening, add a pointed shoe, statement earrings and a smaller handbag.

This is also one of my favorite outfit formulas for travel days when I want to be comfortable but don’t necessarily want to look like I just stepped off a plane.

SHOP THE LOOK

SAVE: Black trousers • soft knit • ballet flats

SPLURGE: Cashmere sweater • tailored trousers • suede boots 

DAWN’S MIX: Save on trendier versions of the pants and spend more on the sweater or shoes you’ll wear season after season

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7. Jeans + Cashmere-Style Sweater + Boots

Sometimes the simplest outfit is the best one.

A beautiful crewneck sweater, flattering jeans and a pair of boots is basically my fall uniform.

Choose cream, camel, chocolate brown, burgundy or navy and you really can’t go wrong.

For daytime, keep everything relaxed with a tote and minimal jewelry.

For dinner, do a little front tuck, add a belt, switch bags and add a beautiful coat.

It’s comfortable. It’s easy to pack. And it works almost anywhere.

SHOP THE LOOK

SAVE: Crewneck sweater • favorite jeans • ankle boots

SPLURGE: Cashmere sweater • premium boots • investment coat

DAWN’S MIX: I’d rather have one beautiful pair of boots I can walk in and wear repeatedly than five uncomfortable pairs that only look good in photos.

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How I Take a Fall Outfit From Day to Night

The secret isn’t packing two outfits.

It’s packing better pieces.

I usually start with an outfit that’s comfortable enough for whatever we’re doing during the day and then change just a few details for dinner.

A larger tote becomes a smaller handbag.

Ballet flats become boots. Or boots become flats thanks to Tieks’ portability. I love keeping a pair folded in my purse to change into later. 

Simple jewelry gets layered with a few more pieces.

A casual jacket gets swapped for a blazer or beautiful coat.

Add lipstick or fragrance and suddenly the same jeans and top feel completely different.

It saves suitcase space and, more importantly, means I’m not spending half the trip changing clothes.

The Fall Pieces Worth Having in Your Closet

You don’t need an entirely new wardrobe every season.

If I were building a fall wardrobe from scratch, I’d start with:

A great pair of jeans • classic trench • cropped jacket • white tee • button-down • striped sweater • soft neutral knit • black trousers • ballet flats • comfortable boots • leather belt • structured bag

Those pieces can create dozens of outfits without your closet being packed with things you only wear once.

And that’s ultimately what I want from my wardrobe – clothes that make getting dressed easier, not harder.

Dawn

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