Do you have trips planned for the fall? Even if you’re not going far or staying long, autumn is a beautiful time to get out for a long drive or maybe a weekend getaway. Those excursions often take us to the mountains where the temperatures are a little cooler. It’s still hot outside, but it’s not too early to get ready to travel in style this fall.

We’ll be exploring a little of Wisconsin in late September, when I speak at a women’s retreat there. And then in October we’re spending a week in the Finger Lakes area of New York, while James attends a landscape photography workshop. So I’m excited about building a small capsule wardrobe for our fall travels.

Comfort is definitely king when I plan my travel wardrobe, but I also want to look stylish, polished and pulled together. I like to look for a few standout pieces for travel that I can mix and match with other basics already in my wardrobe. And I want those selections to be elevated so that I can comfortably wear them for “getting there” as well as dining out or touring.

I started this elevated travel capsule with the 52% organic cotton, 48% recycled nylon stand collar jacket (or here) from Eileen Fisher. You’ll see that I actually couldn’t decide between this beautiful azalea jacket and the reed one, so I purchased both. I intended to return one, but…! The windbreaker is meant to have a full, relaxed fit, but I did size down to a small as I usually do at Eileen Fisher. I love that the jacket features a zip-away hood, and that it both zips and snaps very easily. It has two functional front flap pockets and snaps at the cuffs keep rain and wind at bay.

I already had the azalea linen and cotton jewel-neck top in my wardrobe. I can easily wear it into the fall if I layer it with these pieces. But Eileen Fisher has other sweaters, tees and blouses in this beautiful color as well. I’ll link some in the shopping widget at the bottom of this post.
Next, I added the black washable stretch crepe cargo pants (or here) to the lineup. These lightweight cargo pants feel substantial enough for fall, but still comfortable for car or plane travel. Whereas I generally size down to a small in Eileen Fisher, I ordered the medium in these trending pants. I’ve learned that their more structured pieces run a little smaller than the others.

Above you see me wearing my black athletic sandals with the stretch crepe cargo pants. This is how I would wear them now and for car travel. But when I travel by plane I prefer to wear my sneakers with no-show socks. I think you have several footwear options with these travel separates.

Eileen Fisher has other beautiful pieces that would mix and match with mine. And you’ll find similarly comfortable and versatile black pants in different silhouettes, too. I’ve linked additional options in the shopping widget below.

My black stretch crepe cargo pants will also work beautifully with the reed stand collar jacket I included in my travel wardrobe. I’m going to justify this additional jacket because one might get wet and I’ll need a second just in case. Ha! But truly, they do create completely different vibes. And keep in mind that you can also wear these lightweight but substantial stand collar jackets with other things in your wardrobe, too, such as jeans or cords.

So while the reed jacket pairs beautifully with the black pants, I’ve created a monochromatic look here with the coordinating reed organic cotton cargo pants. Again, I opted for my TTS medium in these zip and button closure pants.

I love the fullness and relaxed fit of this comfortable travel ensemble. But if you’d prefer a more slim fit pant, check out the reed organic cotton tapered pant, also available in black. I’ve worn my Naot Whetu sandals here for a comfortable day of car travel or touring.


For this super casual travel look, I wore the organic cotton French terry top, also by Eileen Fisher. As usual, I sized down to a small for a comfortable fit. This French terry top is a little more substantial than your average cotton tee, but still soft and lightweight enough to wear now. In fact, I wore this second outfit for a mini road trip last Saturday morning.


Just to change things up a bit, this time I wore my Veronica Beard Valentina sneakers. I love that they are a slip on shoe, so they’re perfect for airplane travel if you have to take them off to pass through TSA screening.

I’ll be sharing more comfortable options to help you travel in style this fall. I know that these Eileen Fisher selections are very much on the pricey side. But if you’re trying to thoughtfully build a sustainable wardrobe that mixes and matches and that you can enjoy on repeat, Eileen Fisher is a great brand to consider. As promised above, I’m sharing a few additional EF pieces that work with these beautifully in the shopping widget below.
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You can shop the look through the links in the copy above or through the shopping widget below. Sale prices are not always reflected in the widget, so click through to get pricing info. Remember, if you purchase anything through these links I potentially earn a commission, but at no cost to you. Thank you for shopping through Dressed for My Day. I am grateful!
Thanks so much for dropping in for a little inspiration to help you travel in style this fall. I hope you have a blessed and beautiful day!
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Blessed for My Day
One thing is for sure, we will all experience losses and struggles. We will all grieve. Even believers will feel the depth of the pain associated with the greatest losses. So when you do lose someone you love or experience other catastrophic losses, do not beat yourself up for having those heart-wrenching emotions. Grief is a part of the human experience, and even those who have eternity in their hearts will feel the desperation of great loss.
That said, we do not have to grieve as those who do not know the Lord. We do indeed have hope and a future. And when the ground feels shaky, we can remember that we have a foundation that stands. How do you find your way through the pain of grief and back to the security and warmth of God’s love and faithfulness? You worship Him. Yes, you mourn and weep and struggle. But choose to turn your thoughts to the assurances of God’s Word and spend time in devoted worship of the God who loves you. In time, your grief will become more manageable and the weight of your loss will lessen.
Then Job arose and tore his robe and shaved his head, and he fell to the ground and worshiped. ~ Job 1:20

Love your Eileen Fisher selections. I’m going to have to try some to see how they work for me. I’ve never worn her clothing. Very pricey, but if well made and look terrific, it’s worth the money.
The azalea jacket is beautiful on you!
I just always love your devotional message. That color looks so good on you.
You will adore the Finger Lakes region. My favorite town is Geneseo. Beautiful historic homes, Main Street is full of artsy boutiques and coffee/pastry shops. Let us know where you visit. Autumn is a colorful, magical and romantic tme in the Finger Lakes!
Sounds lovely! I’m not sure exactly where we’ll be but I’m sure I’ll share in time. Thanks for sharing. I’m so excited! We passed through there last year as we returned from Maine and it was just beautiful.
Hi Kay! You look great in your travel wear. My travel lately is extremely limited but I just love your travel jacket with matching tee! So pretty with your light hair and beautiful smile!
You always look smashing in pinks, Kay! I have never worn the azalea color until last winter. You inspired me with a beautiful sweater you modeled. I may also try a shirt as well. Where will you be going in Wisconsin? I live in Madison and hope that our weather is coming your way. We’ve had sweltering heat but storms came through last night and we’ll be in the 70’s all week. Thank goodness!
Yes, we’re supposed to be in the 70s this weekend. Praise the Lord! We’ll be in the Dells and in Door County. Not sure exactly where; James has planned the itinerary and I haven’t really looked at it yet.