1. Maison Martin Margiela Chelsea Boots: I kid you not I wore shoes like this as a 3 year-old and year-after-year they make a comeback with some stylish edits. They go with a lot: rolled up chinos or cargos, cropped trousers, drop-crotch extra long shorts, you name it. I love these Margiela boots because of their slightly sporty appeal that you can dress up or down, along with their two-toned nature to give any head-to-toe look that final pop.

2. Victorinox I.N.O.X Watch: Swiss Army is a brand I’ve long respected. I remember my dad buying me my first swiss army pocket knife on my first camping trip. It was my go-to for everything I needed in a convenient little package. And for most, it continues to serve as a survival necessity whether you’re in the woods or coming home from work needing to open a bottle of Pinot Noir for that 1 de-stresser glass. And now, they’ve come out with its complementary companion: Victorinox I.N.O.X. I had the pleasure of attending the launch party for the release of their new watch just last week up the street from where I live. Point blank, this solid steel (inox in French) watch was designed and built to last and, quite frankly, may be the very last staple watch you’ll ever need (dare I say it?) for the rest of your life. I’ve seen this watch go through it all: being run over by a fire truck and a 64 ton tank, boiled in water, churned through a washing machine for hours, frozen in ice, and dropped from 30 feet. Not a scratch. So feel free take it with you to the extent you take your lifestyle. In fact, use it as a subtle reminder to push your own limits! There’s a good feeling about wearing investment pieces that you don’t have to be so cautious about every waking moment. Bump it against the counter? No sweat. Turn the corner too soon and bang it against the wall? Not a problem. And beyond its durability, it’s a sleek, modern watch you can throw on with a pair of jeans, a suit or with an outfit like you see in this post. Check it out here and put it through your own series of tests… or not and trust that you’re set for life with this timeless timepiece.

3. Wooyoungmi Cropped Trousers: Pants like these are going to carry me through fall. Period. They transition nicely from the end of summer sock-less and good pair of shoes, or with socks wearing a great pair of Chelsea boots like the Margiela numbers I mentioned above.

4. Comme des Garçon Blazer: I own several statement blazers like this one or that one. Each has its own unique quality and I’m a true testament to the fact that your cost per wear on these types of blazers will be down to a bare minimum over the course five plus years. You can wear this black wool-blend lurex distressed blazer with the pants that go with or break it up with a good dark trouser. Any functional hardware that makes the blazer extra special — count me in. There’s a certain “glam” to it that gives nod to a NYE look, which you can certainly plan for, or not and go for a cool deconstructed look.

5. Soulland Fischer Shirt: The next time you tell yourself I could always use a white shirt!, stop and count how many white shirts you do, in fact, have that still look crisp and white, and consider upgrading that notion over a quirky printed one… well, at least I will.

A special thanks to Victorinox for sponsoring a portion of this post. All thoughts and opinions expressed herein are my own.