Two Fall Transition Outfits That Are Comfortable and Look Stylish
Fall is one of those seasons that asks a lot from our closets. One minute it’s 58 degrees, the next it’s pushing 90, and by dinnertime, you’re reaching for a sweater. That’s why I love having a few transitional outfits on hand that layer well, feel comfortable, and still look stylish.
Today I’m sharing two outfits that help me feel put-together even when the weather can’t make up its mind. Both feature pieces that are flattering, versatile, and easy to mix and match as fall rolls in. Let’s start with the first look.
Western-Inspired Denim With a Feminine Twist
This outfit is equal parts modern western and casual chic. Western styles are trending this year, and this dress looks modern and chic. I love the structure of the dress mixed with soft, wearable textures. It’s a great option for those early fall days when you want coverage without feeling overdressed.
Why This Outfit Works
- The soft denim dress is structured but forgiving and easy to move in.
- The shrug adds coverage without warmth, ideal for warm days and cool evenings.
- Accessories tie together texture and tone, creating a cohesive seasonal look.
- Perfect for lunch with friends, casual weekends, or sightseeing.
Frayed Denim Maxi Dress
This denim maxi dress instantly became a favorite. It’s surprisingly soft and drapes nicely without feeling heavy. The frayed hem and seamed waistline add just enough visual interest while keeping the overall look relaxed. The fit is comfortable through the bust and flows gently through the hips, creating flattering curves. Did I mention that it has pockets!!! I’m wearing a size 1, and it fits true to size with room to move.
- Flattering midi-to-maxi length
- Seamed waistline provides gentle shaping
- Lightweight denim with soft structure
- Frayed hem adds a casual fall vibe
Western Harness Boot And A Cow Print Handbag Add To The Western Vibe
These boots are the perfect early fall shoe. First off, I’m not normally a western style fan. But these boots are stylish without being overly rugged, and they pair beautifully with the dress. The slightly pointed toe elongates the leg, and the harness detail gives just a touch of that western flair without going full cowboy.
- Runs true to size
- Easy to walk in with a modest heel
- Pull-on style with a secure feel
- Pairs well with dresses or jeans
The cow-print bag adds just the right amount of western charm to the outfit. It’s fun, functional, and can be worn as a shoulder or crossbody style. I like how it ties in with the boots and gives the entire look a little more personality.
- Fun print without being too bold
- Adjustable strap for crossbody or shoulder wear
- Holds daily essentials easily
- Sturdy construction with clean seams
Jasper Layered Pendant Necklace & Baby Knot Earrings
I finished off the look with this layered Jasper necklace and my favorite knot earrings. The necklace draws the eye downward (always flattering!) and complements the neckline of the dress. The earrings are simple enough for daily wear but still polished.
- Adds vertical interest to the neckline
- Lightweight and easy to wear all day
- Matches with both casual and dressy looks
- Polished but not flashy
Open-Knit Shrug For Added Warmth During Chilly Mornings and Evening
I added this Open-Knit Shrug as a lightweight layering piece, and it worked beautifully. It gives just enough coverage over the arms and shoulders without overheating. The relaxed fit makes it easy to wear over dresses or tops, and the texture adds softness to the denim.
- Easy to layer without bulk
- Provides arm coverage for modesty
- Soft open-weave knit adds dimension
- Great size range, I ordered the XL/3X for an oversized fit.
Hear My Thoughts About This Look
Breezy Neutrals That Say “Chic and Polished”
This second outfit feels like a soft sigh of relief. It’s neutral, polished, and above all, comfortable. I love how each piece moves with you, especially on those days when you’re on the go but still want to feel good in your clothes.
Why This Outfit Works
- Relaxed pieces with structure help you feel dressed without being fussy.
- A neutral palette is easy to mix and match across seasons.
- Comfortable for errands, travel, or casual dinners out.
- Each piece is flattering without clinging or adding bulk.
Crewneck Beach Sweater With Nautical Links Necklace & Stretch Bracelet
This beach sweater surprised me with how lightweight it is. It’s the kind of top you can wear on a warm September day and still feel cool. I sized up to a Large for a more relaxed fit. The texture gives it interest, and it layers well if you need more warmth later.
- Breathable knit for mild weather
- Slightly relaxed fit (wearing a Large)
- Versatile neutral color
- Easy to dress up or down
I kept the accessories minimal but impactful. This nautical necklace and bracelet add shine without overwhelming the outfit. The chunky links give structure and draw the eye upward, especially important when wearing wide-leg pants.
- Bold but wearable jewelry set
- Lightweight and easy on the wrist
- Ties the outfit together
- Adds interest to the sweater
Cotton Linen Wide-Leg Trousers And Celina Bucket Bag
These trousers are one of my go-to styles this time of year. They’re breezy enough for daytime wear but look more polished than shorts or jeans. The wide leg balances the body and skims over hips and thighs without clinging. I’m wearing a large, and they’re generous through the waist and seat.
- Lightweight linen blend
- Elastic waistband for comfort
- Wide-leg cut flatters a fuller figure
- Great for dressing up or wearing casually
This Brahmin bag pulls the outfit together with a slightly structured shape and a timeless design. It holds everything I need while still looking stylish and compact. The soft camel tone matches the wedges perfectly.
- Chic and functional
- Bucket shape with secure closure
- Works well for everyday use
- Neutral tone adds polish
Dressing Between Seasons Doesn’t Have to Be Hard
If fall sneaks up on you like it always does for me, you don’t need a whole new wardrobe; you just need a few well-chosen pieces that can shift with the weather. Think soft sweaters, longer hemlines, breathable fabrics, and accessories that help pull it all together. These two outfits are a good reminder that when you feel good in your clothes, the rest of your day tends to follow suit.
Hear My Thoughts About This Look
FAQs: Fall Transition Outfit Questions
What are the best layering pieces for early fall?
Look for open-knit sweaters, shrugs, lightweight cardigans, and utility jackets. These can be added or removed easily as temperatures shift.
Can I still wear wedges or sandals in the fall?
Yes! Early fall is a great time to wear wedges and open-toed shoes, especially if you’re in a warmer climate. Transition to boots as the weather cools.
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Verse Of The Day
James 4:14 (NIV)
14 Why, you do not even know what will happen tomorrow. What is your life? You are a mist that appears for a little while and then vanishes.
😀 I love the “coastal grandmother” look. The similar tones seem to elevate the style. Now to find pants that fit my short legs.
Loved the denim dress! You looked really great in it.
Love these two outfits!!! Particularly am drawn to the cream colored light weight sweater & slacks!! And the purse is so perfect, too!!!
😊. Found It!!
Love these looks! Both outfits transition so well from late summer to mid or even late fall.
Thanks for sharing.
🙂. I can see me wearing both outfits during this season transition!
Cute outfits! ☺️
🙂 Nice post and great tips.
🙂great post!
😀cute outfits
🙂 Found it! Love the frayed denim dress, but wish it had sleeves.
I love the neutral outfit. It looks so cool and polished. The denim dress is cute too, and different from typical denim dresses.
🙂
😀 really like the lightweight sweater.
😊 I have always loved beige / white on white. You look great in that outfit.
Stephanie
😃 I really like the denim dress and the Coastal Grandma outfit. I’d love to find a very similar dress in my budget. I bet you two really enjoyed the banana split.
I like both outfits! The neutral one is very much in my wheelhouse- I love linen pants in summer- but I’m surprised at how much I like the denim dress because Western has never been for me. I’d want to style it with more boho accessories, but your look is great.
😊. Both are great outfits! Tips are helpful too.
😊The neutral outfit is so pretty. I love the Celina bucket bag!
😀. Love your boots with the denim dress!
I loved all the neutral colors! You always look good in everything you wear.
☺️ I love the Coastal Grandmother Vibe of the second outfit!
😊 Great advice and tips as we transition to Fall. I’m in no hurry, though!
😀. Love the neutral outfit! Perfect for fall!
🙂 Both of these outfits (and how you styled them) are perfect for Fall transition! Thank you!
You look fantastic in both outfits! The “coastal beachy grandma vibe” is a great description..love it!!!
The DQ story made me smile :o) I have found memories of visiting DQ on summer evenings as a child and ordering the Peanut Buster Parfait!! Found it!
😊 in the post Dressing Between Seasons Doesn’t Have to Be Hard.
:). The denim dress looks so cute on you! I would buy the white sweater for fall.
🙂 HOME RUN POST!! I love the denim dress and the fray! I think it could be western or just basic denim. The sweater proved it can be non-western wear. The 2nd outfit is great! So simple and classy. All out of my budget, but still super inspiration!
🙂 found it … love the white linen pants!
🙂 I really like the denim dress for Fall. I plan on getting it once it goes on sale. Great little videos!
☺️ I absolutely love your Joe stories Tania!!! You’re making me want a banana split at our little local ice cream shop that is very close to our home which is not a good thing because I like to go there quite frequently😁. My favorite is the denim dress. It looks great on you, but of course what doesn’t look great on you Tania?
~Lisa~
I lost my subscription for awhile and now just resubscribed. I love the style inspiration you provide as well as the daily scripture reference and Sunday devotional. I am turning 60 in a few weeks and I am hoping that “60 is not old” either. 🙂 I like that you have included video clips now, and I like the new font you use! Fun improvements. Finally…I couldn’t find the smiley and was wondering if it’s okay to ask if it’s hidden somewhere in the copy or also possible to find it on the photos. Thank you!
The smiley is always on a photo, not in the text.
😊 The denim frayed maxi dress looks like it would be perfect for those too-warm-to-be-fall days.
😃 love the suede boots with he denim dress.
😊 Love these looks! I’ll be heading to Chicos today! 😊
😊 I like both outfits and the videos!
🙂 cute denim dress. The beige top and slacks are so versatile.
I love both outfits. I’m enjoying the videos too. 🙂
Hey Tania, my husband & I also have ice cream together at our neighborhood shop. It’s just a nice time. Also just to chill. I really liked that jean dress. For right now, u can wear it as is. & on cool days u can add a little sweater. Very nice. 👍🏻👍🏻☮️☮️☮️✝️✝️
Found it!
While I’m not a fan of frayed clothing, I love all of the jewelry featured and the cow print bag is adorable. I do like the wide leg cotton trousers outfit.
And, I am also enjoying the videos 😉
😊Love the neutral outfit
I love this post!😀 It was 49 here this morning so very timely for the northern part of the US right now!!
😊 Thank You Tania! Love the vibe of both. Ive ordered the dress:)
😃 I love the look of the linen slacks. I just might put those in my Amazon cart.😇 The whole neutral outfit is beautiful.
🙂 I love both of these outfits!
🙂 Love the Coastal Grandmother vibe outfit!
The denim dress is cute, but I’d have to go with a more boho vibe. I’ve never been into western style.
😊LOVE everything about both of these outfits. They are right up my alley!
🙂 Cute outfits! I like the crewneck sweater! I enjoy the videos!
😊Love the denim dress!
Absolutely love the frayed denim dress with the cow hide print purse! Just what I want to wear to a western theme party coming up.
😊 I love both outfits. That jean dress is so cute.
😊Pretty white outfit.
Love those pants and that they are longer and drape. 🙂
😊 I like the necklace.
That’s probably the most flattering denim dress I’ve seen, really like it—
But I’d really like to find that exact chain link necklace you have on— I’m guessing it’s not available. I’ve seen it on you before— it’s perfect!
and Found It!!
That link necklace is from Kendra Scott, but it is very old.
😊 Thanks, Tania!
🙂I love the denim dress! Especially since it has pockets! You look great in it!
😀 I love the grandmother vibes
🙂I really love the denim dress
😊. Pretty transitional outfits. Cute story about the little date over a banana split 🥰. You and Joe are such a sweet couple.
☺️
😊I like the coastal grandma outfits.
Love the denim dress from Chicos! 🙂
: ) Love the beige outfit.
😊 The banana split bribe worked! And it was fun. You look amazing in both outfits.
I do like the videos.
🙂 I try to keep a light sweater with me wherever I go in the fall. I really like the linen white trousers and love the Celina bucket bag.
🙂Found it
:)The denim dress is very cute! I like the linen pants outfit, as well, but the wrinkles in linen make me crazy!
🙂 love the denim dress outfit
🙂
I adore the second outfit.
The sweater reminds me of the “Mersea” ones you see advertised. Have you tried one of their’s? I’d love to see it on a real person…
I’ve never heard of them.
Love both of the featured handbags. The Brahmin is a beauty.
🙂 I like the chic and polished look. I think I will attempt to purchase more casual but chic and polished outfits.
😊
😊love the all neutral outfit
I really like the linen pants with the beach sweater. To me a great pulled together look. The hand bag is a great addition.
I don’t wear a lot of jewelry, but with this look it works.
Thank you, You keep me looking current.
What is the little button you are wearing on the right chest area? I have seen it before but not sure what it is for. Also, I really like hearing the verbal comments.
It is a microphone for when I do the videos.
I like the sweater and the bucket bag! 😊
Love the linen pants. I have a light blue pair that are just perfect for our Florida weather.
I definitely favor the second outfit, but, unlike me, you really can wear a western-inspired look well!
🙂 Cute frayed denim dress! Love the white linen pants, I have black ones that are my go to pants, can dress then up or dress them down! Thanks for sharing!
🙂 Love the coastal grandmother vibe!
🙂 How fun that you and Joe had a fun impromptu date. Love the beach sweater!
😊 love, love, love the linen pants and sweater outfit!
found it 🙂
love hearing your voice, hope you talk to us more often!
the western theme you have going with the denim dress is so cute!
The beach sweater and linen pants are so pretty. 🙂
🙂 I am totally a beach Gramma, well I used to be. We lived in Boca for about 10 years. Love the denim dress.
🙂 love the coastal grandma outfit. Very cute
Love both outfits, they look great in them.
Love the Jean dress!
Found it 😊
🙂 Found it! Cute outfits and I love the accessories.
Tania, I have followed your blog for a few years now and have never heard you talk! I think I love you even more now with your sweet southern sound! Lol. Never realized until I heard your DIL that I’ve never heard you speak!
Oh and nice touch with adding our first name to the beginning of our emails. Great suggestions today!
🙂 I really like the linen sweater and loose pants. It’s great to read your Joe stories. Have a blessed week.
I love the linen like pants. I have a similar pant in black and wear them dressy or at the office. 🙂
😀love both outfits