American Classic Style Is Always A Winning OOTD

American Classic is one of the most timeless styles. This post presents its key elements and how to put them together into great outfits.

Contents

Key Elements of American Classic Style
Polo Shirt Styling
Tweed Skirt and Cardigan
A Simple American Classic Style Recipe: Baseball Jacket with Denim
Riding Boots, Tweed Skirt and Motorcycle Jackets
The Button-down Shirt, Jeans and Cardigan
Skirt with (faux) Twinset
Black Turtleneck plus Jeans and Blazer Equal Instant Style
American West Coast Style Leather Blazer
Trick to Wear a Short Jacket over a Blazer
American Classic Style Icons and Their Famous Looks
Wrapping Up American Classic Style

Key Elements of American Classic Style

Here is a list of Must-have items

Polo shirt
The iconic white button-down shirt (replace each year)
The blazer in navy blue or West Coast Style brown leather
Straight jeans
Riding boots
Around the knee tweed skirt
Grandpa cable knit cardigan and cashmere cardigan
Bias-cut slip dress for summer
Corduroy or denim skirt
Button-front skirt
Turquoise cuff
White summer dresses (more on American women wearing white in summer)
Baseball and/or utility jacket
Denim or trucker jacket
Hawaiian shirt, skirt or dress
Pearls
Oversize sunglasses

The next sections show how to pull it all together, and lead you to guides on how to style the respective item(s).

Polo Shirt Styling

An above the knee straight denim skirt in a dark wash looks great when paired with a thin striped polo shirt and a belt. Make sure that the buckle’s picks up the hardware of your denim. To complete the vibe go with wedge sandals and Jackie O type sunglasses.

details of belt, buckle, watch — Details of belt and watch

over 50 years old style blogger in Jackie O sunglasses and denim skirt — Oliveo denim skirt, The Limited thin striped polo shirt, Kieselstein Cord belt and belt buckle, Ray Ban Jackie O. sunglasses, Tissot stone watch, and suede wedge sandals

Tweed Skirt and Cardigan

The iconic tweed skirt looks best with a short or long-sleeve cashmere sweater and driving shoes or riding boots. In winter, a cardigan is added for some extra insulation. It hasn’t to be a real twinset like in Euro Chic. Create a faux twinset with a neutral color cardigan that works with the other (neutral) colors of the look. More on great tweed skirt looks.

influencer in American Classic tweed skirt Argyle sweater, cardigan — LandsEnd Argyle cashmere sweater under cashmere cardigan worn over tweed skirt and tights with Vince Camuto suede boots accessorized with multiple strings of pearls

A Simple American Classic Style Recipe: Baseball Jacket with Denim

Stylist tip: A baseball jacket with striped Tee and denim is always a winner.

The following look shows a striped T-shirt, denim and baseball jacket combination a simple recipe for an casual, posh of American Classics outfit. BTW, the shirt is made in the USA from sustainable resources. I love when style meets sustainability.

woman in America Classic style — Front view jeans skirt with Tee

style blogger Nicole in versatile leather jacket and jean skirt — Zoom-in on accessories

fashion blogger wearing an American classic look with baseball jacket and a knee length denim skirt — Michael Kors baseball leather jacket with Oliveo denim skirt, Anne Klein T-strap pumps, Chanel bag and striped 3/4 sleeve T-shirt c/o Marine Layer

Riding Boots, Tweed Skirt, and Motorcycle Jackets

Riding boots and everything equestrian like horse buckle belts are key elements of the style. Also motorcycle boots, motorcycle vests, motorcycle jackets, motorcycle coats, and motorcycle shearlings, motorcycle booties. Just think, what does one need to explore the Southwest. The tweed skirt is an icon in all collections from American designers. More on how to style a tweed skirt at the link.

Stylist illustrating how to wear riding boots, tweed and leather motorcycle jacket — Graham and Spencer motorcycle jacket, Oliveo chambray button down shirt, GNW tights, Eddie Bauer tweed skirt, Sanchez riding boots

The Button-down Shirt, Jeans and Cardigan

US fashion blogger in button-down top with jeans skirt — Side view of look with button-down top

influencer in Chambray button-down shirt, denim skirt, sandals — Oliveo Chambray button-down shirt, GNW cardigan, denim skirt, Kieselstein Cord belt and buckle, gold sandals, Picasso print scarf, and statement bag

Summer Skirt with (Faux) Twinset

Jill.E Designs tablet tote close-up to show size — Details of accessories

Nicole with a floral skirt, sweater, cardigan and Jill.E tablet tote — Isaac Mizrahi cardigan, Lands Ends sweater, Ray Ban sunglasses, Eric Michael wedge sandals, and Loft skirt, tablet tote c/o Jill.E Designs and necklace c/o Almo Jewellery

stylist in cardigan, shirt, pantyhose, Mary Janes and straight bottom — Ray Ban Jackie O. sunglasses, Oliveo chambray shirt, G-III red suede skirt, Jones New York striped cardigan, Apostrophe Mary Janes, pantyhose and DIY necklace

Black Turtleneck plus Jeans and Blazer Equal Instant Style

Today I keep it short with just an update on my outfit and a little styling trick. I like to refer to the look as my American West casual style. The outfit is a great for Casual Friday outfits. The cashmere sweater instead of a T-shirt makes this casual look stylish at any age.

Stylist tip: A black turtleneck sweater plus jeans and a suede blazer are instant American casual posh style.

#fashionover40 Casual office look with short jacket over a blazer — Orvis suede blazer, Isaac Mizrahi cashmere turtleneck sweater, London Jean boyfriend jeans, Aldo leopard print pony-hair pumps and pearls for a posh casual Friday office look

Trick to Wear a Short Jacket over a Blazer

When a jacket is shorter than your blazer, fold the blazer underneath so it would not show. The jacket’s belt allows for this little styling trick when tied tightly. In this outfit, the blue gloves and blue beret and the satchel complete the outerwear.

#fashionover50 casual winter outerwear — Andrew Marc motorcycle shearling jacket worn over the outfit shown above with Michael Kors leopard print satchel bag and heeled duck booties

The American West Coast Style Blazer

American Classic outfit idea West Coast vibe — Orvis suede blazer over GNW Luxe sweater with white Newport News leather pants, Gloria Vanderbilt pumps, Kieselstein Cord belt and buckle, and statement necklace

The Iconic White Button Down Shirt

The most important thing of a button-down shirt in general, is the placement of the second button. You know, these awkward gaps that may occur when that button is in the wrong place.

An easy fix: Add a push button.

Look for a wrinkle-free one. Most the time, it’s one wear and back into the laundry. Thus, unless ironing is your hobby, make sure you get a low maintenance version. Replace the shirt every year. Sweat and deodorizer yield yellow spots under the arms. Not stylish at all.

Tip: About 10 to 15 min before washing, add white vinegar on the underarm fabric to slow that “aging” process down. Wash as usual.

Replace your white button-down shirt every year to have a crisp appearance. The shirt looks great with pants, straight skirts or jeans like in the photo below. A classic blazer makes the look work appropriate for a business casual style work place.

example outfit of American iconic button down white shirt styled with flared jeans, blazer, high heels, belt and necklace — Ralph Lauren silver snake imprint pumps, studded headband, statement belt, amber modernist necklace, Sam Edelman bucket bag, Vittoria Virani linen blazer, quartz earrings, white sun-protective shirt c/o Coolibar and flared jeans c/o Femme Luxe

American Classic Style Icons

Jackie Kennedy, Grace Kelly, Meg Ryan as Kathleen Kelly in You’ve Got Mail, Michelle Obama, Karlie Kloss and Melania Trump are some of the best known American Classic style icons. They are famous for wearing pearls.

Pearls are always appropriate. – Jackie Kennedy

Jacqueline Kennedy in Venezuela from Wiki Commons — Jacqueline Kennedy in Venezuela during December 1961 trip to South America. Source JOHN F. KENNEDY PRESIDENTIAL LIBRARY AND MUSEUM. Author Cecil Stoughton, White House. This file is a work of an employee of the Executive Office of the President of the United States, taken or made as part of that person’s official duties. As a work of the U.S. federal government, it is in the public domain.

The inspiration for the look below was Mrs Kennedy wearing light capris and a fine knit short sleeve sweater at the beach.

American Classic Jackie Kennedy inspired summer outfit — Side view of American Classic weekend summer outfit

fashion blogger in casual summer look — A classic Jackie Kennedy inspired outfit to stay warm on a chilly summer evening. Star denim jacket, knit sweater, capri and nude Anne Klein sling backs to elongate the legs

The Jackie O. oversize sunglasses are an eternal classic. As a child I wondered whether they were a fashion statement or whether Jackie tried to hide behind them. Find out which frames are best for you with my free face shape finder.

stylist in American Classic spring outfit with Ray Ban Jackie O. sunglasses — Burberry Trench coat over G-III skirt with Celine bag, Apostrophe Mary Janes, and Ray Ban Jackie O. sunglasses

A great Karlie Kloss famous look inspiration is her camel wool coat with jeans and sneakers outfit. Don’t forget Princess Patricia‘s cool monochromatic look with cable-knit sweater, pearls, boat-shoes, and white denim with a pop of red on a sailing boat in Monaco.

Wrapping Up American Classic Style

This style is the most timeless and ageless style. No matter who your style icon is, take the inspiration. However, make the look your own. In the example with the skirt, the material (suede leather) is so me. In the look with capris, adding a denim jacket is so me.

Like the red skirt outfit? You might also like to see how I wore this skirt in fall with another cardigan and a vest.

You can find outfit ideas with patriotic attire for Independence Day as well as another American Classic OOTD at these links.