Unless otherwise specified, all sizes in this post are listed in men's.
1. A Hanes fleece pullover hoodie that comes in a vintage wash. These garment-dyed sweatshirts are a comfortable and fashionable foundation to layering your next fall outfit. Wear it under a denim jacket or pea coat, or throw it on by itself to stay cozy indoors. No matter how you wear it, or where, you'll look good in it.
2. A crewneck long-sleeve T-shirt because it's the foundation to any great ensemble. When it's chilly outside, one of these in white will give you an extra layer of warmth. And, in the spring months, break out a bolder color and it will be the star of your outfit.
3. A Levi's black denim jacket that will have you ready for a night out on the town. Whether you pair it with a dress shirt or a T-shirt, all eyes will be on this classic piece that looks better the more you wear it.
4. A short-sleeve button-down shirt for every occasion where the dress code is business casual, but you still want to look like yourself. Whether you're rocking it in a solid color or a bold print, this slim-fit shirt will help you stand out.
5. A pair of slim fit chinos that are going to give you some range. Go from business during the day to party after work seamlessly with these — they're wrinkle-resistant, have added spandex for stretch, and quick-drying wicking fabric, which means these pants will hold up no matter what kind of day or night you have when you're wearing them.
6. A pair of slip-on sneakers because having a couple of these simple-yet-sharp shoes in different colors so you can mix and match them with your favorite pants and shirts is always a good idea. They'll keep your feet comfortable and your casual fit stylish.
7. A pair of gray Skechers athletic shoes that will hold you down in the gym and maybe after the gym, too. Made with memory foam cushion on the inside and lightweight knit fabric on the outside, you may find yourself wearing these sleek, comfortable sneakers even when you're not getting a workout in.
8. A crewneck sweater you're going to want to wear for almost every occasion. Running to the store for groceries? Heading to a birthday dinner party? Making a big presentation? Time to unwind after work? This crewneck sweater works for all of this and more, so grab a few in a couple in different colors and prints.
9. A relaxed fit hoodie that will make you look good even when you're just lounging around your home. And when you pair this with the matching sweatpants, you're not just relaxing, you're styling.
10. A pair of Levi's regular fit jeans that have a zip fly and some extra room in your thighs, so this classic fit of Levi's moves with you. Stand up, and they hang loosely but they're not baggy. Sit down, and they give you the room you need without making you feel like you're going to burst out of them.
11. A pair of matching sweatpants to pair with your new favorite hoodie. Bring the whole outfit together and elevate the lazy weekend look with these sweats. They're so comfortable you probably won't want to take them off, but they're also so stylish, why would you ever not wear them?
12. A striped polo shirt will upgrade the classic polo shirt look. It's perfect for an afternoon outing or business lunch, plus the striped print on this T-shirt accentuates your pecs and will give your chest area a strong silhouette.
13. Three pairs of retro-inspired striped crew socks that will make you feel more than ready the next time you visit a no-shoes home. These moisture-wicking cotton blend socks look so good, they might attract as much attention as your sneakers.
14. A slim-fit traditional Oxford shirt, in a nontraditional color. At this point, you probably already own one or even two white Oxford dress shirts, but don't be afraid to incorporate some color in your business casual attire with this pomegranate colored button-down version.
15. A long-sleeve henley shirt that's a classic staple for the fall and winter months. Whatever color you get them in, they will add a layer of protection against chilly weather, as the three-button collar will bring out your chest and necklines.
16. A zip-up hoodie that won't make you look like a mess on your way to the gym. Just because you're about to get sweaty, doesn't mean you have to look like it. This zip-up is made from a lightweight knit fabric that keeps heat in and has thumbhole cuffs, so you're going to be able to keep the sleeves in place during that next cardio session.
17. A pair of lace-up oxfords in gray will make your next business casual occasion pop a little more. Ditch your traditional brown or black dress shoe for this gray-colored dressy-yet-casual shoe, for a mix of old-school style and new-school flair.
18. A flannel shirt to keep you cozy all season long. The lumberjack look is timeless, whether you button it up or you leave the front unbuttoned and layered over a T-shirt.
19. A short-sleeve T-shirt in charcoal black that will go with everything you own. This shirt works when you're just hanging around the house, but throw this on with a dark pair of jeans and a leather jacket and you're ready for a night on the town. This will be one of the most versatile shirts in your wardrobe.
20. A slim fit long-sleeve dress shirt because it's a wardrobe staple. Even if you already own a couple, this version, in lightly checkered blue or plaid, is going to add more versatility to your closet.
21. A collared polo shirt that doesn't really need any introduction. Chances are you probably already own a couple of them, but there's never a bad time to stock up your supply with a couple of new colors, especially when you can get them at this low price.
22. A pair of smooth black ankle rain boots to keep your feet dry and fashionable — after all, just because it's raining, doesn't mean your style has to suffer. These rubber boots are lighter than other rain boots, but just as water resistant as their higher-end counterparts. They're slip-resistant, too, so you'll have less to worry about when walking in the rain.
23. A moisture-wicking running hat that you will want to wear even on a leisurely stroll. This cap is as functional as it is fashionable, with perforated side vents designed to keep your head cool whether you're sprinting, jogging, or even just hanging out under a hot sun.
24. A camo print windbreaker that will make you look good whether you're wearing it while running, walking, or getting hit with some less-than-perfect fall weather. This water- and wind-resistant lightweight jacket is perfect to layer up during changing season.
25. A fitted hoodie with a ribbed hem that you definitely won't want to wear during your next workout. This isn't your regular activewear hoodie — it's more like a nice sweater with a hood.
26. A stretch canvas shirt jacket, also known as a shacket, that is the new fall wardrobe staple. Perfect for layering, nice enough for a holiday party, and stylish enough for a night out, buying one of these will give your closet some versatility beyond your basic hoodies and sweaters.
27. A pair of 100% cotton Wrangler cargo pants that have the pocket space you need to carry all your stuff, and the relaxed fit will help you not get weighed down by your goods.
28. A chore jacket that is too nice to wear for actual chores. With its sturdy collar, button-up front, and multiple pockets, this jacket makes it easy to turn the volume up on any casual outfit.
29. A pair of Levi's joggers that look as good as jeans but are as comfortable as sweats. With a tapered leg and a slim fit throughout, these pants will have you looking like you're ready for a night out, even though they're comfortable enough to wear on your morning run.
30. A pair of Wrangler slim-fit khaki pants that will go with practically everything in your closet. Whether you have a presentation to give at work, or you're grabbing weekend brunch, these pants will fit for any occasion.
31. A long-sleeve button-down denim shirt that is the perfect cross between jacket and dress shirt. This wardrobe staple looks good under a blazer or worn by itself. Get it in a couple of colors to keep your wardrobe interesting.
The reviews for this post have been edited for length and clarity.