November’s sure creeping up, ain’t it? You can’t stop that month. Whether you’re a fan of The Office or not, that quote was on a loop in my head at the end of October – and sure enough, November crept in, and now it’s in full swing. Couldn’t stop that month! I know wool coat season will be here soon – at least for us in the Midwest (they’re even forecasting snow this weekend!). And while I don’t love the six months of winter we get here, I am excited to embrace the season – and the outfits that come with it. But before the gloves, scarves, and heavy layers arrive, I’m still loving lightweight trench coats, skirts with sheer tights, and finding new ways to style my basic white T-shirts for fall. Here’s to new fall outfit inspiration based on real-life looks I actually wore — no endless scrolling required!
1. white t-shirt + trench coat + black jeans + ankle boots + bucket tote
Whether I’m staying home or exploring “the city,” I like to wear – you guessed it – the basics. You just can’t go wrong! And you know what else you can’t go wrong with? Elevated basics – like this trench coat. Special little details are perfect for refreshing a piece without losing the timeless essence of a classic staple.
This trench coat was part of my round-up of favorite Sézane pieces, but since it’s definitely a splurge, you don’t need this exact one to get the look. I’ve been seeing more and more trench coats with interesting linings (and wow – this one is such a great alternative!) that add just the right amount of style without veering too far into “trendy.” Because too many trends can easily date an outfit!
I leaned into the classic vibes with a basic white tee, black jeans, and ankle boots. A leather bucket tote is the perfect finishing touch – practical, stylish, and effortlessly chic.
2. turtleneck + mini skirt + tights + riding boots + houndstooth blazer
Preppy, academia-inspired looks are the epitome of fall to me, so each week you’ll see me wearing at least one outfit that embodies this style! With the weather a bit cooler now, I’ve started wearing tights under my skirts occasionally, and I love the different vibe they give. Bare legs are great (see below), but tights add a sleek, polished touch that feels both stylish and weather-appropriate.
Once upon a time, someone said (who was that again?) that you can’t wear brown and black together – but that’s definitely not an outfit rule I live by. In fact, I love these colors together! Of course, the shade pairing matters, but I even enjoy layering different tones for more depth and interest. In this outfit, I think the brown really pops against the all-black base of a turtleneck, skirt, tights, and boots.
3. white t-shirt + mini skirt + plaid trench coat + knee-high boots
You’ve seen me wear this black skirt and white tee so many times – and I’m not embarrassed. I’m proud! Since day one, I’ve been all about wearing what you have rather than constantly buying new. Of course, I still shop and add new pieces to my wardrobe – shopping is not the point – but there’s a big difference between thoughtful shopping and getting caught up in impulse hauls every month. Fewer really is better!
And if (or when) you do start to feel a little tired of your staples – it happens – I like to make them feel fresh again through layering or by adding just one new piece to the mix. The cardigan adds a layer, which makes the proportions look more interesting, and the plaid trench coat (the new piece) really brings the style.
(And perhaps it’s worth noting — before you think I’m wearing the same pieces like this black skirt -over and over without washing them (ha!) — that sometimes it takes me a few weeks to gather enough outfit inspo that I’m actually wearing out and about for one week’s content. Most of the time, my day-to-day outfits look a lot more like home and mom life.)
4. white tee + red cardigan + leopard print trench coat + jeans + red socks + loafers + bucket bag
You may remember this trench coat — it was the top-favorite item from my Nordstrom Anniversary Sale wishlist. Though it sounds contradictory, even as a bold piece, I knew I’d actually get a lot of wear out of this leopard print trench coat. After all, leopard print is a neutral.
While leopard print looks amazing with other neutrals, it also (surprisingly!) pairs beautifully with bold pieces too. That’s why I styled it with my favorite red cardigan and matching red socks — and if you saw my lips, you’d notice a matching red lip as well. I balanced out the statement elements with wardrobe staples (jeans, loafers, and a simple bag), but honestly, you could finish the outfit however you like. Personal style, to me, is what truly completes a look!
5. turtleneck + leopard print midi skirt + knee-high boots
Not every fall outfit needs lots of layers. Sometimes, a single printed piece supported by neutrals and classic staples is all it takes to make your look shine. A leopard-print skirt (or other bottoms, like pants) can look effortlessly stylish when paired with simple pieces.
Think of the statement item as the main character and your other pieces as the supporting cast. For fall, a turtleneck and tall boots complete the look perfectly!
6. blazer + white tee + black pants + loafers + scarf
I’m all for using accessories in new ways — and how fun is this outfit idea of tying a scarf around your waist? We’ve talked about different ways to wear a scarf before, and now here’s one more styling idea to add to the list. I love how wrapping an oversized silk scarf around your waist adds an extra touch of style — and even a pop of color!
You can try this look in the fall or winter, but it would also be so cute for a beachy, vacation vibe in spring and summer. I kept the rest of the outfit simple with a white tee (yes, again — don’t worry, I have about ten of these), dress pants, and loafers.
7. turtleneck + black jeans + houndstooth blazer + tote bag
Polished yet preppy perfectly sums up this outfit. If you love preppy style but aren’t into mini or plaid skirts, this look still delivers that classic, preppy vibe — polished, timeless, and effortlessly put together using wardrobe staples.
Tucking a turtleneck into your jeans creates a clean, structured base, while layering a longer houndstooth blazer on top flatters the silhouette and balances proportions. The timeless print also adds interest and an autumnal touch. I love both flat and heeled knee-high boots, but a slight heel adds just the right amount of extra polish. To finish the look, a Longchamp bag is the perfect choice for this style!
Fall Outfit Inspo That’s Easy to Find (And Recreate!)
Have you noticed the change on Pinterest lately? It’s so hard to find things — I miss the old days! Now, searching for outfit inspo often means scrolling through AI-generated content, product pins, and sponsored ads that take up the whole feed to the point where you can’t see anything original. I hope these outfit posts give you some inspiration without making you wonder, “Wait, is that AI?” It’s so tricky these days!
Despite the algorithm challenges, Pinterest is still a platform I use daily. So, shameless plug — go ahead and follow My Chic Obsession so you’ll always be rewarded with something good. (No AI content from us!)
Love your site…don’t change a thing!
Thank you for the kind words, Teri!
Hi Carolyn,
I found you during the pandemic and have loved your posts since. Bought your book, watched you build your home and family and wish you all of the best. Love your style!❤️
Aw, thank you so much for your faithful support, Mary!