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Timeless & Effortless: 20 Classic Outfit Pairings That Always Work


Timeless & Effortless: 20 Classic Outfit Pairings That Always Work


Timeless and Tasteful

We don’t all have the luxury of spending an hour figuring out what to wear, especially if we’re heading to the office. When it feels like you’ve exhausted your options, it might be time to go back to the classics. Check out this list below for some simple outfit pairings that will still make you sparkle.

a woman sitting in the back of a green carLance Reis on Unsplash

1. Blazer And Slip Dress

A cute option for the working professional and the professional partier, the blazer and slip dress combo is a great day-to-night option. For the day, wear a neutral shirt with a similar neckline in case you need to shed the blazer, but let those scandalous shoulders fly when the day is done.

Mikhail NilovMikhail Nilov on Pexels

2. Suit And Loafers

This power pairing never goes out of style. A matching suit with a basic t-shirt just makes your outfit look casual enough for a day out, especially when you take the blazer off. Match with your favorite loafers, and you’ll be classy and comfortable for the day ahead.

gershootsgershoots on Pixabay

3. Button Up And Blue Jeans

Like the business casual powerhouse you are, a button-up and blue jeans are an incredibly versatile option for work or play. You can play with hemlines, jean cuts, and various accessories to attune this everyday outfit to your personal style.

File:Skinny Jeans (Unsplash).jpgPete Bellis petebellis on Wikimedia

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4. Minidress And Tall Boots

This stylish pairing is perfect for a dinner party or a night out. Wear a tighter dress with knee-high boots for a more polished look, or wear a floral dress and cowboy boots if you prefer the boho vibe.

woman wearing white mini dressTamara Bellis on Unsplash

5. Maxi Skirt and Slouchy Shirt

The ultimate comfort outfit for a day out in the sun. Maxi skirts are a great option for breathable wear, while still protecting you from the sun, and a half-hazardly tucked-in t-shirt will give you an aura of effortless beauty. In the cooler months, swap your t-shirt with a sweater, and pop on some wool tights.

Pavel DanilyukPavel Danilyuk on Pexels

6. Maxi Dress And Sneakers

A maxi dress will always feel a little bit dressed up, especially if you’re not heading to the beach. Pair them with sneakers, however, and you have a comfortable outfit for a day out with your friends. If you want to go the extra mile, pop on a baseball hat for added sun protection.

person in white sneakers standing on gray concrete floorKadarius Seegars on Unsplash

7. Blazer And Pencil Skirt

A staple for the working woman, a matching (or color-matching) jacket and skirt combo will make you the fashion icon of the office. If your job requires more formal wear, pair it with a button-up, or go with a blouse or shirt in a complementary color.

woman in black blazer and black and white skirt standing beside black metal standVladimir Yelizarov on Unsplash

8. Trench Coat And Ballet Flats

Trench coats can be quite overwhelming if you don’t know how to style them. If you’re looking for something casual, pair your coat with flats, jeans, and a knit top, and you’ll look positively Parisian.

woman in brown coat wearing brown hat standing on snow covered ground during daytimeAlexandra Iva on Unsplash

9. Fitted shirt and wide-legged pants

We’re not talking JNCO jeans, but having your silhouette flair at the bottom does give the appearance of a smaller torso and longer legs. This combination is great for the professional world, but can also be tailored to a more casual look depending on the type of shirt you wear.

man in brown polo shirt and blue denim jeans holding black smartphoneAltin Ferreira on Unsplash

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10. Vest And Wide-Legged Jeans

This western-inspired duo is a super cute way to layer without looking too formal. If you’re sensitive about your stomach region, a vest is a great way to wear something fitted to your waist without tucking in a shirt, and you can wear whatever patterns you prefer.

Léo GilmantLéo Gilmant on Pexels

11. Little Black Dress With Accessories

The little black dress is a necessity in any and all wardrobes due to its versatility. You can glam it up with your best jewelry and highest heels, or dress it down with flats, sneakers, and an oversized t-shirt.

Woman poses on a balcony overlooking a cityscape.Cherosi on Unsplash

12. Denim Jacket And Midi Dress

For something casual and comfortable in cooler months, the denim and midi dress combination is a great option. It’s easy enough to throw on without putting too much time into your outfit pairings, but it looks good enough to make everyone think you’re a style icon.

woman standing on seashore near bridgeTim Mossholder on Unsplash

13. Denim-On-Denim

The Canadian Tuxedo has made a reappearance in fashion of late, and it just works so well. Go monochromatic with a matching vest or jacket paired with jeans or a skirt, or find two washes of denim that go really well with one another. The safest way to achieve this look is to pair light or dark washes with white or black.

Hardeep SinghHardeep Singh on Pexels

14. Graphic Tee, Blazer, And Jeans

A common fit for the everyday employee, you can wear this outfit to the office and then to the bar. This look works best if you’re comfortable, so it’s especially good to find jeans that fit your body type.

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15. Monochromatic Outfit

Sometimes it just takes one color to create an eye-catching outfit pairing. Certain stores will sell tops and bottoms in the same colors for this very purpose, but even combining articles of clothing in the same color family will create a statement outfit without even trying.

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16. Cardigan And Full Skirt

This modest look is a great way to look fashionable and stay warm in the winter. Reminiscent of the '50s “poodle skirt” silhouette, the cropped or French-tucked cardigan will lengthen your legs and make you cute to boot.

Engin AkyurtEngin Akyurt on Pexels

17. Black And White

Black and white outfits will always, always work. Black dress and white jacket? Yep. Black pants and a white shirt? You got it. Striped black and white shirt with a white skirt? Of course. Keeping a selection of black and white basics in your closet means you’ve always got an outfit on hand.

Đường Hoàng   GiangĐường Hoàng Giang on Pexels

18. Linen On Linen

Linen on linen is a great way to keep cool in the summer, especially if you’re working in a professional setting. Pair a button-up with some straight-leg trousers, or a cropped tank with some wide-legged pants or a skirt. You’ll look like you came straight from the yacht.

Mikhail NilovMikhail Nilov on Pexels

19. Dress and A Leather Jacket

If you want to add some edge to your favorite sundress, a leather jacket is the way to go. Pair your dresses with a leather trench or cropped jacket to keep warm and look cool.

Khalid BenfanichKhalid Benfanich on Pexels

20. Sweater And Bike Shorts

Also known as the Princess Diana staple, this outfit is the perfect blend of sporty and casual. Pair an oversized crewneck with your favorite biker shorts, and top the look off with sneakers and sunglasses. You’ll look exactly like the people's princess.

woman in yellow sweater riding black bmx bikeAmir Kiani on Unsplash