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Weekly Outfit Recaps
See what I wore, how I styled it, and what mood I was in each day.

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What I Wore in Florence (aka When I Chose Fashion Over Function—and Still Had the Time of My Life)
Latest Trip Outfits Lesli Olson Latest Trip Outfits Lesli Olson

What I Wore in Florence (aka When I Chose Fashion Over Function—and Still Had the Time of My Life)

From Aperol spritzes and sightseeing to blisters and bike-induced panic, this trip was one for the books. Brant and I spent four full days in Florence, Italy to celebrate 19 years of marriage and my 45th birthday, and I wore every outfit I packed. Here’s everything I wore, what worked (and what didn’t), and a few honest reflections from a midsize traveler embracing both comfort and confidence.

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19 Years, 4 Days, One Incredible City: Florence with Brant
From My Life Lately Lesli Olson From My Life Lately Lesli Olson

19 Years, 4 Days, One Incredible City: Florence with Brant

We spent four days in Florence celebrating our 19th anniversary and my 45th birthday — just the two of us, Aperol spritz in hand, walking until our feet gave out and our hearts felt full. From climbing the Leaning Tower of Pisa to belting out Shoop at an Irish pub, this trip was equal parts pasta, connection, and magic. Here’s a peek into the places we wandered, the food we devoured, and a few moments I never want to forget.

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What I Wore in SoCal (aka When Friendship and Sunshine Outweighed My Insecurities)
Latest Trip Outfits Lesli Olson Latest Trip Outfits Lesli Olson

What I Wore in SoCal (aka When Friendship and Sunshine Outweighed My Insecurities)

Five college roommates, reunited after 23 years, in sunny SoCal. You’ll find me in comfy (but stylish) spring-to-summer looks—light layers, elastic-waist barrel legs, and my trusty hat—on car trips, pool days, tequila tastings, and sunset nights. And yes: despite body changes, I still wore the swimsuit, struck the pose, and joined the fun. A reminder to take the trip, no matter what.

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Weekly Outfit Recap | Easy Looks, Dirty Hair, and a Barrel Leg Jeans
Weekly Outfit Round-Ups Lesli Olson Weekly Outfit Round-Ups Lesli Olson

Weekly Outfit Recap | Easy Looks, Dirty Hair, and a Barrel Leg Jeans

A slow and cozy week back in real life after a busy season of travel and contests. This week's outfits were all about comfort, layering, and finding joy in easy style — including a few surprise barrel-leg moments I didn’t even realize I wore. Sharing everything I wore from Monday to Saturday in this laid-back, real-life outfit recap.

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What I Wore in Homer, Alaska
Latest Trip Outfits Lesli Olson Latest Trip Outfits Lesli Olson

What I Wore in Homer, Alaska

A cozy girls' weekend in Homer, Alaska filled with charcuterie boards, Bravo marathons, hot tub hangs, and just the right amount of adventure. We stayed at the beautiful West Wind Cabins, explored town, and soaked up the slow pace — all while keeping comfort and style top of mind. Sharing everything I wore (plus a few must-shop favorites) from a perfect spring break getaway.

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