It’s not easy picking out clothes as a guy. Trends change, seasons turn, and suddenly the paisley button down you wore last year becomes the laughing stock of the office. Frankly, a lot of men just don’t really care about their clothes are content cycling through their closet’s content no matter how dated a particular piece may be.

And that’s certainly fine. As I’ve said before, I disagree with the saying that clothes make the man, but there are some occasions in which it would benefit you to pay a thought or two about what you’re wearing — especially this time of year.

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It’s not a good look to roll into fall wearing the same distressed jeans and worn-out sandals that you lived in all summer. Whether you go out to dinner or out for drinks, to the mall or to the grocery store, women like to see a subtle air of sophistication, represented by some forethought in your appearance.

The good news is that you don’t need to break the bank to dress like a gentleman; all you need is these five wardrobe staples and you’ll be able to fool anyone into thinking you’re the King of Cool.

  • Classic Watch

It’s a bold move to begin this list with an accessory over a piece of apparel, but there is possibly nothing more iconic than a classic timepiece. You can browse all sorts of nice watches for men to ensure you find the right one that fits your style. Whether you prefer a timeless leather brown wrist strap or you opt for a black, bold-faced number, you can count on your watch to deliver that polished, debonair look.

  • Dark Denim

Men, if the back pocket of your jeans displays the permanently faded outline of your wallet, then it’s time to invest in a new pair of denim. Forget the acid wash, fancy stitching, embellished rhinestone, and all the other bells and whistles associated with high-fashion jeans.

When it comes to denim, all I wear these days — and all you’ll ever need — are a go-to pair of Levi’s jeans. There are several reasons why I swear by this staple: for starters, they’ll never go out of style, unlike stonewashing and artificial distress marks; they’re extremely durable, holding up for 1-2 years no matter how hard I wear them; they’re inexpensive and won’t break the bank; and best of all, they’re comfortable as hell.

Grab a dark, boot cut style and say hello to your new best friend.

  • Earth-Toned Henley

We get it — you want to look stylish without putting in the effort to dress up. Queue the timeless Henley thermal, the All-American fall favorite in terms of under layers. That pack of Hanes white-tees probably got you through summer, but chances are that they’re now yellowed with sweat stains – and even if they weren’t, that’s not the direction to dress if you want to look like a fashion-minded gent. Henleys have a popular waffle texture that makes them immediately recognizable. They’re snug in the most flattering places and hang loosely everywhere else for unparalleled comfort. Grab one in a neutral olive green that can be paired with any ensemble you put together. 

  • Stately Shoes
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They might not be in immediate eyesight, but shoes can really make or break an outfit, so keep those Vans and Converse in the closet for the times you want to dress to impress. Other alternatives you should lean toward are classic leather boots and loafers. These guys can be dressed up or down, matching with pretty much everything but basketball shorts (hopefully you know not to wear these out, anyway).

If you don’t feel right without wearing a dash of color on your feet, then check out Samuel Hubbard’s chukka low tops. The nubuck fabric looks great with business casual attire and they come in a variety of shades that will add a pop to your outfits. Those who are adamant about the sneaker game should go with something a little classier like a demure pair of New Balance shoes — these kicks have seriously elevated their style game since being dubbed Dad shoes way back when.

  • Messenger Bag

Last but not least, upgrade from your old school briefcase in favor of a stylish messenger bag that can carry all your daily essentials. You’ll instantly receive a style upgrade just by switching out this accessory staple.

Choose your own way by mix and matching these wardrobe must-haves to ensure you never go out of style this season, next year, and beyond.