I think it depends on what timeless means to you! I have a pair of black enclosed pedal pushers that I prefer. They’re straight, they fit so well, and I’ve always tucked them into my boots, so I don’t mind the ankle showing. I also have a pair of skinny jeans that fit me perfectly. This is the best denim I’ve ever owned! Expensive but I buy mine used online. Other good ones are AYR and Paige, but both better for skinny. My friend loves Madewell’s Perfect Vintage jeans, and they have a nice straighter fit, but I will say that I loved Madewell jeans 10 years ago, and I have a few from that era in good condition , but everything I’ve purchased from them in the last 3-4 years, it lasted less than a year, so it’s no longer worth it to me.
For boots, everyone where I live has them, but I can highly recommend the Blundstone Chelsea boots. I bought mine in 2020 so I could go on impromptu hikes if I needed to extend my lockdown walks (I live in an area with easy hiking access from the city) and I walk 5-6 miles per day, where I do them every day, and I just had to resole them for the first time. They still look amazing too. I have the ones with more of a heel, a little different from the flat Chelseas everyone has, and I love them. Otherwise, Repetto boots are my favorite city boots, mine lasted a decade, but they are expensive. They don’t do Black Friday but they will go on sale in January when the French sales launch!
Hope this helps with either decision!
