I believe it relies upon what timeless means to you! I’ve a pair of black Closed pedal pushers which can be my go to. They’re straight, they match so nicely, and I at all times have them tucked into my boots, so I don’t thoughts the little bit of ankle exhibiting. I even have a thin pair of denims from them that match brilliantly. They’re the perfect denim I’ve ever owned! Dear however I purchase mine second-hand on-line. Different good ones are AYR and Paige, however each higher for skinnies. My good friend loves the Excellent Classic Denims from Madewell, they usually’re a pleasant, straighter minimize, however I’ll say I adored Madewell denims 10 years in the past, and have some from that point in good situation, however every thing I’ve purchased from them within the final 3-4 years has lasted lower than a 12 months, so not value it for me anymore.
For boots, everybody the place I stay has these, however I can extremely suggest Blundstone Chelsea boots. I purchased mine in 2020 so I may go for impromptu hikes if I wanted to increase my lockdown walks (I stay in an space with simple mountaineering entry from the town) and I stroll 5-6 miles a day, the place them on a regular basis, and I simply needed to resole them for the primary time. They nonetheless look superb too. I’ve those with extra of a heel, a bit completely different than the flat Chelseas everybody has, and I really like them. In any other case, Repetto boots are my go to metropolis boots, mine have lasted a decade, however they’re dear. They don’t do Black Friday however they may go on sale in January when the French sale is on!
Hope that helps with both determination!