No matter what season you're in, it always helps to have an arsenal of outfit ideas in your back pocket for whenever you're rushing out the door in the morning, dressing for an important meeting, or perhaps even have a dinner date on the books that you really want to step it up for. The influx of new fashion arrivals coupled with my slight case of warm-weather dressing fatigue has me already and unabashedly planning my October and November looks and, as always, doing a little shopping while I'm at it. So now, I'm sharing some of my historical go-to outfits. To see how some of my favorite fashion girls wore the nine classic looks and shop them along the way, just keep scrolling.
1. Blazer + Jeans + Kitten Heels
No matter what color blazer, jeans, or shoes you wear, you can never really go wrong with this one.
2. Minidress + Ankle Boots
Depending on the weather, you can also throw a sweater over your shoulders.
3. Long Coat + Leather Pants + Sneakers
I 100% do not look as cool as Pernille when I wear this combo, but it's still a good one—I promise.
Shop more sizes at Nordstrom.
4. Suit + Heels
Need to look smart? Throw on a suit and heels and you will always look good.
Shop the matching Amaya Vest ($125) and Norah Trousers ($155).
5. Sweater + Midi Skirt + Kitten Heels
This easy pairing is as comfortable as it is cute.
6. Fleece + Jeans + Ankle Boots
My many fleeces were on heavy rotation last fall, and I can't wait to bring them back again. Bonus points if you also throw on some layering chains to elevate the look like Caroline.
7. Sweaters + Slacks
Knitwear is turning out to be an even bigger fall trend than usual, so double up on the sweaters (or pick a pre-styled combo) and pair with your favorite trousers.
8. Blazer + Turtleneck + Miniskirt
Any shoes will do the trick, of course, but the kitten heels look especially lovely.
9. Statement Jacket + Jeans + Ankle Boots
I love a statement jacket for making jeans look polished and applicable for a ton of settings.
This article was previously published and has since been updated. Up next? The 6 Trendy Fall Outfits Our Market Editor Is Wearing Now
-
If I Saw You in Any of These 15 Summer-to-Fall Transitional Outfits, I'd Think You Hired a StylistNice taste.
-
Put Down the Black and White Pants—This Is the Richer Color You Didn't Know You NeededElegant and on-trend.
-
What You Should and Should Not Wear to Every Major Sporting EventFrom a Liberty game to the French Open.
-
10 Outfits Europe's Chicest Dressers Are Wearing When They're *Not* on VacationStaying local is cool.
-
Just to Be Clear, *These* Are the Pants Fashion People in L.A. Are Wearing Instead of Basic JeansSpotted in Paris too.
-
The Coolest Outfits of Summer 2025 Are Actually the Laziest—Let Me ExplainEasy does it.
-
I Just Created 5 Incredibly Chic Summer Outfits From Amazon for Under $190Cool looks for less.
-
Don't Pack Up Your Sweaters Just Yet—Cool Fashion People Are Repurposing Them in the Chicest Way for SummerAll the outfit inspiration is inside.
