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Blast from the Past: Office Fashion Then and Now – Would You Still Wear It?

Reflecting on iconic workwear styles from years past and considering how modern professionals might wear—or replace—them today.

By Medha deb

Created on Jun 19, 2025

Reflecting on iconic workwear styles from years past and considering how modern professionals might wear—or replace—them today.

Blast from the Past: Would You Wear These Today?

Fashions evolve, but the memories—and sometimes the photos—linger. At Corporette®, we love looking back at pieces we’ve featured on the blog, reflecting on our initial reactions and how time has shaped our opinions. Are those styles still wearable? If so, how would you incorporate them into your current office wardrobe? Or have you swapped them for something new and updated?

The retrospective journey below draws on select highlights from August 20 posts in years past, examining what was once on-trend and how you might (or might not) want to revisit those looks for today’s professional scene.

August 20, 2018: The Brooks Brothers Sheath Dress
August 20, 2010: Platform Shootie/Booties
August 20, 2008: Nanette Lepore “Don’t You Dare” Jacket
Modern Recommendations for 2025
Frequently Asked Questions (FAQ)

August 20, 2018: The Brooks Brothers Sheath Dress

The Look: A structured sheath dress, $398 at Brooks Brothers, with a concealed back zip—a detail that made it particularly appealing at the time. The commentary noted excitement about the early advent of the loafers-with-dresses trend, which has since become a key styling choice in many professional wardrobes.

Retro Review: Even several years later, this dress retains its appeal: clean lines, durable tailoring, and an office-friendly silhouette. However, sheath dresses are not as dominant in 2025’s workwear landscape as they were a decade ago—largely due to changing attitudes about comfort, body inclusivity, and work-from-anywhere flexibility.

If You’d Wear It Today:

Pair with a sleek blazer for instant polish.
Style with modern loafers or a flat for comfort and trend relevance.
Consider a wide belt to introduce contrast or show off the waist if desired.

For those looking for something similar but more current, keep reading for updated dress recommendations.

Modern Alternatives: Sheath Dresses We’d Recommend Now

M.M.LaFleur – Renowned for high-quality, versatile work dresses in comfortable knits and practical shades.
L’Agence – Elegant sheath styles with contemporary tailoring and luxurious fabrics.
J.Crew & J.Crew Factory – For budget-friendly, office-appropriate dresses and separates.
Modern Citizen – Emphasizing minimalism with unexpected details.
Jenni Kayne – Elevated basics with a modern, California-inspired vibe.
Even more affordable options can be found at Quince and J.Crew Factory.

While the classic sheath has softened in popularity, those who love the look can easily update it with accessories and modern footwear.

August 20, 2010: Platform Shootie/Booties

The Look: Michael Antonio platform shoes, described as a cross between a bootie and a heel—commonly called a “shootie.” These were a wardrobe go-to at the time, particularly for those who preferred added support from a strap or boot-like fit.

Retro Review: The shootie/bootie style, with towering platforms, was considered very stylish at the time (and comfortable for heel fans because of the straps). Looking back from 2025, these shoes seem distinctly of their era and less aligned with this decade’s surge in minimalism and all-day comfort.

2010: The Platform Shootie	2025: Footwear Trend
Chunky heels and high platforms	Block-heeled loafers, ballet flats, sleek low-heeled mules
Closed-in design, often with straps	Open silhouettes, breathable knits, more flexible flats
Heavier, bold statement	Neutral shades, lightweight feel, understated elegance

If You’d Wear It Today:

Try balancing the boldness of the shootie with streamlined pants or midi skirts.
Opt for updated versions in more neutral colors and with less dramatic platforms, if possible.
If comfort is your priority, consider modern block-heeled or flat shoes that offer support with a lighter overall look.

Modern Alternatives: Nude-For-You Sandals for 2025

Look for “nude-for-you” sandals in shades that closely match your skin tone, for a lengthening effect and versatile wearability.
Popular brands now provide a spectrum of nude shades, moving away from the “one nude fits all” idea of the past.
Styles to consider: sleek ankle-strap sandals, sophisticated slides, and classic loafers in a nude or blush palette.
Always gauge your office’s dress code: sandals are still not suitable for every formal environment.

August 20, 2008: The Nanette Lepore “Don’t You Dare” Jacket

The Look: Nanette Lepore’s “Don’t You Dare” suit—originally highlighted as “Suit of the Week.” This ensemble featured a knit blazer with button details on the hip pockets and cuffs, ruched sleeves, and a belt at the back. The skirt included ruffled details. Initial impressions veered from a bold “yes!” to post-purchase hesitation, reflecting the cyclical, subjective nature of fashion.

Retro Review:

Pros: Unique knit texture, interesting detailing, the wide neckline, shrunken fit that feels fresh thanks to its tailored silhouette.
Cons: Ruffled skirt and bold styling now appear less wearable or versatile. The knit fabrication is also less associated with modern, sharp suiting.
Even in 2008, the popularity was mixed, and 2025’s preferences lean toward cleaner lines and classic suiting shapes.
Personal Attachment: Nostalgia can make an item feel special, as with the author’s memory of a short-sleeved Nanette Lepore jacket worn during a significant moment (engagement!).

Ultimately, this suit is “a LOT OF LOOK,” and perhaps not for everyone—even back then. The shrunken blazer, however, gets another chance in today’s fashion cycle.

Shrunken Blazers: The 2025 Revival

Shrunken blazers are having a resurgence, with brands like J.Crew and J.Crew Factory revisiting the schoolboy blazer (in cotton and sweater knit).
Luxury options, such as Smythe’s classic and asymmetric blazers, and L’Agence’s tailored pieces, offer updated interpretations.
Pair a shrunken blazer with high-waisted trousers or a midi skirt for modern balance.

Modern Recommendations for 2025

While some past trends can feel out of place today, others are prime for reinvention. If you’re looking to update your professional wardrobe, focus on these areas:

1. Sweater Jackets

Soft structure and comfort remain key for offices in 2025.
Brands to try: M.M.LaFleur Jardigan (the original sweater-jacket hybrid), L’Agence, J.Crew, Modern Citizen, Jenni Kayne.
Budget-friendly options at J.Crew Factory and Quince.

2. Comfortable, Versatile Dresses

Ponte, crepe, or stretch-knit dresses offer flexibility for desk-to-dinner wear.
Look for discreet closures (like concealed zippers), pockets, and washable fabrics.

3. Footwear Trends

Loafers—especially block-heeled versions—are the new go-to. They balance comfort with a structured look.
Ballet flats, slides, and updated Mary Janes are back, often featuring soft leathers and flexible soles.
Neutral sandals can work in creative or business-casual settings, but always check office dress codes first.

4. Blazers and Suiting

Schoolboy and shrunken blazers offer a nod to past trends but are made modern with updated fabrics and tailored fits.
Pair with wide-leg trousers, cropped pants, or streamlined dresses for a look that is current but classic.

5. Color and Pattern

Neutral palettes dominate, but don’t be afraid to incorporate accent colors or subtle patterns for personality.
Monochromatic dressing is trending for its streamlined effect and ease of outfit creation.

Style Evolution: What Drives Change?

Many factors contribute to how workwear evolves—cultural shifts toward comfort, the rise of hybrid and remote work, and a growing appreciation for individual style expression. Some notable drivers include:

Comfort-first dressing: Stretch fabrics, flats, and sweater jackets reflect modern workers’ priorities.
Gender inclusivity and diversity: Workwear has become less prescriptive and more adaptive.
Sustainability: More professionals seek higher-quality, fewer pieces that offer longevity and flexibility.
Return of nostalgia: Brands often revisit old trends, updating them for today’s context—hence the renewed interest in items like shrunken blazers or classic loafers.

Frequently Asked Questions (FAQ)

Q: Why do certain workwear pieces become outdated?

Workwear trends shift in response to broader changes in workplace culture and societal priorities: comfort, flexibility, sustainability, and personal expression all influence which items stay relevant.

Q: How can I make a vintage or outdated piece look modern?

Pair with current staples such as structured blazers, updated footwear, or minimalist accessories.
Opt for a modern fit: tailoring can turn an old piece into a wardrobe hero.
Accessorize thoughtfully—sometimes swapping a dated belt or jewelry can make all the difference.

Q: Are sheaths and pencil skirts still appropriate for the office?

While not as dominant as in previous years, sheath dresses and pencil skirts remain classics. Update them with soft suiting, modern flats or loafers, and a mindful approach to unique details like fabric and closure.

Q: What’s the best way to try a new workwear trend?

Start with accessories or layering pieces like a new shoe style or a statement blazer.
Shop budget-friendly brands for trend-driven experiments, saving investment funds for timeless staples.
Observe your office’s culture and dress code to guide your choices.

Inspiration for Your Next Workwear Update

Don’t shy away from past favorites if they suit your taste—update them with a new perspective.
Focus on comfort, versatility, and personal flair to make your work wardrobe feel fresh and functional for 2025.
Stay open to evolving trends, but trust your instincts: the best wardrobe choices are the ones you feel confident in.

Have you kept, reworked, or replaced pieces like these from previous years? How would you style them for the modern office? Share your thoughts!